case study on inorganic chemistry

Department of Chemistry

College of Natural & Agricultural Sciences

Welcome to the UCR Department of Chemistry Case Study Collection  

Supported by funding from the National Science Foundation TUES (Transforming Undergraduate Education in STEM) program and the U.S. Department of Agriculture Higher Education Challenge Grant Program, we are creating a series of problem-based case studies that we hope instructors will implement during the first two years of their undergraduate chemistry program. This site is intended to provide general chemistry and organic chemistry instructors with a cohesive set of cases that correlate with the two year introductory chemistry curriculum, and improve student achievement in carrying out higher order problem solving and critical thinking. We also aim to create learning activities that help students see the link between chemistry and real-world issues, thereby increasing student interest and engagement in chemistry and science.

As the collection of cases grows, most of them will be published at the National Center for Case Study Teaching in Science (NCCSTS). Links will take you to the NCCSTS site, where the case materials will be freely available for you to download. If you are an instructor and wish to receive the answer key for any of the cases, you can sign up as a member of the NCCSTS site and the site administrators will send you answer keys via email.  For cases not published at the NCCCSTS, we will provide direct links to the case materials, and instructors can email us to gain access to answer keys. We are still in the process of publishing the entire case collection, but we will ultimately have two or three cases for each quarter of general chemistry and one or two cases for each quarter of organic chemistry (at UCR, general chemistry and organic chemistry are each taught in a three-quarter, year-long sequence). Additionally, we will soon be creating Blackboard interfaces which can be used by your students to answer the case questions online. Once we create these Blackboard interfaces, we will provide downloadable zip files that can be uploaded into your own course management site. We expect these downloadable files to be available by the end of summer 2013. It is our hope that these materials improve the teaching and learning environment in your classrooms. If you have questions or comments about any of the cases, do not hesitate to contact us.

Dr. Jack Eichler (Principal Investigator; general chemistry; [email protected] )

Dr. Leonard Mueller (co-Principal Investigator; general chemistry; [email protected] )

Dr. Richard Hooley (co-Principal Investigator; organic chemistry; [email protected] )

General Chemistry Problem-Based Cases

• “The Global Warming Debate: A Case Study” Note: This case is done in the 3 rd  or 4 th  week of our first general chemistry course, and is done in order to provide an introduction to data analysis and scientific reasoning. The answer key and teaching notes are available upon request ( [email protected] ). Case Study Intro ( Click Here ) Case Study Activity ( Click Here ) Blackboard Test File for Case Study Questions ( link to zip file ) (Note: The questions for the case activity were downloaded from a Blackboard course management site, however the test file can be uploaded into any course management system that is capable of importing IMS files).  
• Fossil Fuels – “Liquid Coal: Producing Liquid Fuel from Non-Petroleum Sources" Case Study at NCCSTS ( Click Here )  
• Acid/Base Chemistry - "Using Oceans to Fight Global Warming?" Case Study at NCCSTS ( Click Here )  
• Kinetics - "Corn Ethanol: Using Corn to Make Fuel?" Case Study at NCCSTS ( Click Here )  
• Gas Laws - "Hydrogen Powered Cars: The Wave of the Future?" Case Study at NCCSTS ( Click Here )

General Chemistry Clicker Cases

• Atomic Theory – “History of the Atom – Part I” Case Study at NCCSTS ( Click Here )

Organic Chemistry Problem-Based Cases

• "Organic Chemistry and Your Cellphone: Organic Light-Emitting Diodes"  Case Study at NCCSTS ( Click Here )  
• Chirality and the Origins of Life  Case Study at NCCSTS ( Click Here )

Honors Organic Chemistry Problem-Based Cases

“Selective COX-II Inhibitors - the Story of Vioxx®: A Case Study in Drug Discovery"  This case was done in order to facilitate a high level discussion in our third quarter honors organic chemistry seminar. If you have questions about the case or need assistance with the answer key, email Dr. Richard Hooley ([email protected]).

 Case Study ( Click Here )  

“Overcoming Bacterial Antibiotic Resistance - the Story of Penicillin, Augmentin ®  and Vancomycin” This case was done in order to facilitate a high level discussion in our third quarter honors organic chemistry seminar. If you have questions about the case or need assistance with the answer key, email Dr. Richard Hooley ([email protected]). Case Study ( Click Here )  

We’re fighting to restore access to 500,000+ books in court this week. Join us!

Internet Archive Audio

• This Just In
• Grateful Dead
• Old Time Radio
• 78 RPMs and Cylinder Recordings
• Audio Books & Poetry
• Computers, Technology and Science
• Music, Arts & Culture
• News & Public Affairs
• Spirituality & Religion
• Radio News Archive

• Flickr Commons
• Occupy Wall Street Flickr
• NASA Images
• Solar System Collection
• Ames Research Center

• All Software
• Old School Emulation
• MS-DOS Games
• Historical Software
• Classic PC Games
• Software Library
• Kodi Archive and Support File
• Vintage Software
• CD-ROM Software
• CD-ROM Software Library
• Software Sites
• Tucows Software Library
• Shareware CD-ROMs
• Software Capsules Compilation
• CD-ROM Images
• ZX Spectrum
• DOOM Level CD

• Smithsonian Libraries
• FEDLINK (US)
• Lincoln Collection
• American Libraries
• Canadian Libraries
• Universal Library
• Project Gutenberg
• Children's Library
• Biodiversity Heritage Library
• Books by Language
• Additional Collections

• Prelinger Archives
• Democracy Now!
• Occupy Wall Street
• TV NSA Clip Library
• Animation & Cartoons
• Arts & Music
• Computers & Technology
• Cultural & Academic Films
• Ephemeral Films
• Sports Videos
• Videogame Videos
• Youth Media

Search the history of over 866 billion web pages on the Internet.

Mobile Apps

• Wayback Machine (iOS)
• Wayback Machine (Android)

Browser Extensions

Archive-it subscription.

• Explore the Collections
• Build Collections

Save Page Now

Capture a web page as it appears now for use as a trusted citation in the future.

Please enter a valid web address

• Donate Donate icon An illustration of a heart shape

Inorganic chemistry : concepts and case studies

Bookreader item preview, share or embed this item, flag this item for.

• Graphic Violence
• Explicit Sexual Content
• Hate Speech
• Misinformation/Disinformation
• Marketing/Phishing/Advertising
• Misleading/Inaccurate/Missing Metadata

plus-circle Add Review comment Reviews

33 Previews

2 Favorites

DOWNLOAD OPTIONS

No suitable files to display here.

PDF access not available for this item.

IN COLLECTIONS

Uploaded by station03.cebu on January 5, 2021

SIMILAR ITEMS (based on metadata)

Thank you for visiting nature.com. You are using a browser version with limited support for CSS. To obtain the best experience, we recommend you use a more up to date browser (or turn off compatibility mode in Internet Explorer). In the meantime, to ensure continued support, we are displaying the site without styles and JavaScript.

• View all journals
• Explore content
• About the journal
• Publish with us
• Sign up for alerts
• Open access
• Published: 10 August 2024

Intramolecular chalcogen bonding activated SuFEx click chemistry for efficient organic-inorganic linking

• Minlong Wang   ORCID: orcid.org/0000-0001-8631-3523 1 ,
• Jiaman Hou 1 ,
• Hainam Do 2 ,
• Chao Wang 1 ,
• Xiaohe Zhang 1 ,
• Ying Du 1 ,
• Qixin Dong 1 ,
• Lijun Wang 1 ,
• Fazheng Ren   ORCID: orcid.org/0000-0002-5485-6862 1 &
• Jie An   ORCID: orcid.org/0000-0002-1521-009X 1  

Nature Communications volume  15 , Article number:  6849 ( 2024 ) Cite this article

1 Altmetric

Metrics details

• Materials chemistry
• Synthetic chemistry methodology

SuFEx click chemistry demonstrates remarkable molecular assembly capabilities. However, the effective utilization of alkyl sulfonyl fluoride hubs in SuFEx chemistry, particularly in reactions with alcohols and primary amines, presents considerable challenges. This study pioneers an intramolecular chalcogen bonding activated SuFEx (S-SuFEx) click chemistry employing alkyl sulfonyl fluorides with γ-S as the activating group. The ChB-activated alkyl sulfonyl fluorides can react smoothly with phenols, alcohols, and amines, exhibiting enhanced reactivity compared to SO 2 F 2 . Excellent yields have been achieved with all 75 tested substrates. Pioneering the application of S-SuFEx chemistry, we highlight its immense potential in organic-inorganic linking, considering the critical role of interfacial covalent bonding in material fabrication. The S-SuFEx hub 1c , incorporating a trialkoxy silane group has been specifically designed and synthesized for organic-inorganic linking. In a simple step, 1c efficiently anchors various organic compounds onto surfaces of inorganic materials, forming functionalized surfaces with properties such as antibacterial activity, hydrophobicity, and fluorescence.

Similar content being viewed by others

SuFExable polymers with helical structures derived from thionyl tetrafluoride

C–H activation

Toward azo-linked covalent organic frameworks by developing linkage chemistry via linker exchange

Introduction.

The important role of click chemistry in modern science has been recognized by the 2022 Nobel Prize in Chemistry 1 , 2 . Recently, a new generation of click chemistry, sulfur fluoride exchange (SuFEx) promoted by Sharpless, Moses and co-workers, has demonstrated impressive molecular assembly capabilities 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 . Benefited from the diverse collection of SuFExable hubs 3 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , SuFEx chemistries offer tremendous scope for exploring chemical space and wide range of sulfuryl-heteroatom connectors to meet more diverse linking needs, thus enabling its rapid development as the technology of choice in organic synthesis 18 , 19 , 20 , drug discovery 21 , 22 , 23 , chemical biology 24 , 25 and polymer chemistry 26 , 27 , 28 (Fig.  1a ). Typically, SuFEx chemistries require activated substrates 3 , 29 , 30 or additional activators 5 , 6 , 31 to broaden the SuFEx substrate scope. At the same time, intramolecular activation of sulfonyl fluorides has been relatively unexplored. Of note, the effective utilization of alkyl sulfonyl fluoride hubs in SuFEx chemistry remains elusive, particularly in their reactions with aliphatic alcohols and primary amines 4 , 5 , 6 . Alkyl sulfonyl fluorides are less electrophilic, which often requires high base loadings and extended reaction times to react with nucleophiles. However, alkyl sulfonyl fluorides are not well compatible with strong bases due to the facile deprotonation of α -H 30 , 32 . Therefore, significant challenges persist in effectively activating alkyl sulfonyl fluorides (Fig.  1b ).

a Diverse collection of SuFExable hubs and their applications in organic synthesis, drug discovery, chemical biology and polymer chemistry. b State of the art strategies aiming at activating alkyl sulfonyl fluorides and current challenges. c Chalcogen bonding. d This work: intramolecular ChB-activated SuFEx chemistry. e Clickable platform for efficient covalent organic-inorganic linkages based on the S-SuFEx chemistry.

Non-covalent interactions represent a powerful and promising activation mode in organic synthesis 33 , 34 , 35 , among which chalcogen bonding (ChB) has been attracting more and more interest 36 , 37 , 38 , 39 , 40 , 41 . The low-lying C − S σ* called σ-holes is available for interaction with electron-donating atoms, particularly O and N 41 , 42 , 43 (Fig.  1c ). ChB interactions have gained the relatively wide applications in medicinal chemistry 44 , solid–state chemistry 45 , material science 46 , and anion recognition/transport 47 . Recently, ChB interactions have increasingly found applications in organic synthesis, regulating conformation and activating various functional groups, such as nitro derivatives 36 , carbonyl compounds 48 , imine groups 49 , and alkenes 50 . Notably, ChB activation provides an alternative that avoids the need for stoichiometric Lewis acids used in traditional synthetic methods 38 . Considering the validated use of stoichiometric Lewis acids to activate sulfonyl fluoride 31 , we postulated that leveraging intramolecular ChB interactions could enhance the efficiency of SuFEx chemistry.

In this study, alkyl sulfonyl fluorides bearing γ-S were designed and synthesized. γ-S will engage in intramolecular non-bonding 1,5-sulfur···fluorine interactions, enhancing the activity of sulfonyl fluoride group towards nucleophilic attack. These S-SuFEx hubs were synthesized through a straightforward thiol-ene reaction using thiols and ESF. Remarkably, our results revealed that S-SuFEx hubs did react smoothly with a wide variety of O , N -nucleophiles, exhibiting one of the broadest substrate scopes among all the reported SuFEx reactions 5 , 6 . The high reactivity of S-SuFEx chemistry will enable the facile connection between thiols and various O , N - nucleophiles using ESF as the linkage (Fig.  1d ). Within the realm of potential applications of S-SuFEx chemistry, our initial emphasis was placed on the construction of organic-inorganic linkages. This focus arises from the recognized importance of interfacial covalent bonding, representing a pivotal approach for integrating the tailoring capabilities of organic molecules with the diverse properties of inorganic materials. This strategy has seen extensive utilization in the fabrication of functionalized materials 51 , 52 . Nevertheless, establishing efficient linkages between a wide range of functional organic molecules and inorganic materials remains a significant challenge. Herein, we introduced S-SuFEx hub 1c , distinguished by the presence of a trialkoxy silane group, designed and synthesized to facilitate efficient organic-inorganic linking. The sulfonyl fluoride group within 1c readily engages with a spectrum of O , N - nucleophiles through S-SuFEx chemistry. Simultaneously, its trialkoxy silane group adeptly anchors onto surfaces of inorganic materials. Employing 1c , we have achieved a one-step creation of functionalized self-assembled monolayers (SAMs) on glass surfaces. These monolayers exhibit diverse properties based on the covalently attached organic compounds, including antibacterial activity, hydrophobicity, and fluorescence. Ultimately, this protocol establishes a versatile clickable platform, offering an efficient and practical method for constructing a diverse range of customizable organic-inorganic hybrid materials (Fig.  1e ).

Development of intramolecular chalcogen bonding activated SuFEx click chemistry

In order to improve the reactivity of alkyl sulfonyl fluoride towards nucleophilic attack through intramolecular non-bonding 1,5-S···F interactions 53 , we designed the alkyl sulfonyl fluorides bearing γ-S (S-SuFEx hubs). These S-SuFEx hubs were synthesized via the robust thiol-ene reaction between readily available thiols and ESF. To evaluate the reactivity of S-SuFEx hubs, alkyl sulfonyl fluoride 1a was used as the model compound, and its analog 2a/2b without γ-S was used as the control compound. Significantly, the SuFEx reaction of 1a with phenol 4a performed well in a near quantitative yield to give the desired product 5a using 0.5 equiv. of BTMG (2-tert-butyl-1,1,3,3-tetramethylguanidine) as the base (Fig.  2a , Eq. 1 ). Under identical reaction conditions, 2a/2b reacted with phenol very slowly, delivering sulfonate 6a/6b in only 23%/16% yield (Fig.  2a , Eq. 2 ). These results exhibited that the intramolecular ChB interaction has dramatically improved the efficiency of the SuFEx reaction. Changing the thiol precursor from 1a to 1b / 1c leads to a similar high reactivity. Nor Me 3 Si- group or (EtO) 3 Si- group has an impact on the reactivity of S-SuFEx reaction, and (EtO) 3 Si- group was well retained under the reaction conditions (Fig.  2a , Eq. 3 and 4 ). To further prove the effect of ChB on this reaction, 1a and 1b were oxidized to the corresponding sulfones ( 3a and 3b ), which hindered the formation of ChB. As expected, the SuFEx reaction between 3a and 3b with phenol gave sulfonates 7 in extremely low yield (Fig.  2a , Eq. 5 and 6 ).

a SuFEx reaction efficiencies of different alkyl sulfonyl fluorides. Reaction conditions: alkyl sulfonyl fluoride (0.3 mmol), phenol (0.3 mmol), and BTMG (0.15 mmol) were stirred in MeCN- d 3 (1 mL) for 2 h at room temperature. b Variation in phenol concentration over time in its reaction with 1b , 2b , or SO 2 F 2 . Reaction conditions: alkyl sulfonyl fluoride 1b or 2b (0.3 mmol), phenol (0.3 mmol), and BTMG (0.15 mmol) were stirred in MeCN- d 3 (1 mL) for 2 h at room temperature. SO 2 F 2 was introduced by needle from a balloon filled with the gas.

Subsequently, we explored the activation of alkyl sulfonyl fluorides through intermolecular ChB interaction. Dibutyl sulfide (1.0 equiv.) was introduced into the SuFEx reaction to act as the intermolecular ChB donor. However, despite this addition, there was no observed enhancement in the reaction efficiency between 2b / 3b and phenol (Fig.  2a , Eq. 7 and 8 ). This outcome unequivocally highlights that the efficiency of SuFEx reactions can only be augmented through intramolecular ChB interaction. To compare the reactivity of SO 2 F 2 , 1b , and 2b in SuFEx reactions, we monitored the variation in phenol concentration over time for these three reactions (Fig.  2b , Supplementary Table  2 ). The results indicated that 1b exhibited significantly higher reactivity compared to 2b and even surpassed SO 2 F 2 , widely acknowledged as one of the most efficient SuFEx hubs with excellent reactivity towards phenols 3 . These findings substantiate the effectiveness of ChB activation in S-SuFEx chemistry as well.

Design of S-SuFEx click hub for organic-inorganic linking

After establishing the S-SuFEx chemistry, we devised S-SuFEx hub 1c to enable efficient covalent organic-inorganic linkages. The chemical structure of S-SuFEx hub 1c comprises three functional moieties: a sulfonyl fluoride group, a ChB donor, and an anchoring group (Fig.  3 ). The sulfonyl fluoride group reacts with a variety of O , N -nucleophiles, forming a covalent bond that links the organic compound to the hub. Concurrently, the ChB donor enhances the reactivity of the sulfonyl fluoride through intramolecular non-bonding 1,5-S···F interactions, initiating the S-SuFEx reaction. The trialkoxy silane group can effectively anchor the organic moiety linked to the hub onto the inorganic surface by the formation of stable Si–O–X covalent bonds, as its capability to react with hydroxyl groups on the surface of inorganic materials has been extensively validated 54 . The synthesis of 1c has been achieved via a straightforward thiol-ene reaction between a prevalent silicon coupling agent, 3-mercaptopropyltriethoxysilane, and ESF.

Design of the S-SuFEx hub 1c for efficient covalent organic-inorganic linking.

We continued to explore the reactivity of 1c towards different O , N -nucleophiles. Given the high reactivity of trialkoxy silane group towards water, its analog 1b with a trimethyl silane group was employed as the model compound for the study to avoid the hydrolysis of the trialkoxy silane group during the aqueous workup process.

The S-SuFEx chemistry with phenols

We initiated our exploration by examining the reaction between S-SuFEx hub 1b with phenols. Upon optimizing the reaction conditions (see Supplementary Section  2.1.5 ), it was determined that the addition of 0.5 equiv. of BTMG represented the most favorable condition for triggering the reaction. No supplementary silicon additives or elevated temperatures, typically employed in accelerated SuFEx click chemistry, were deemed necessary. The required amount of BTMG could be further reduced by employing a sacrificial base, such as triethylamine (see Supplementary Section  2.1.8 ). The substrate scope investigation revealed the successful reactivity of the S-SuFEx hub with a wide range of phenols (Fig.  4 ). Phenols, whether containing electron-donating or electron-withdrawing groups on the aromatic ring, demonstrated comparable reactivity and were smoothly converted into sulfonates 8 . Various functional groups, including fluoride ( 8d ), chloride ( 8e ), hydroxy ( 8j ), amide ( 8k, 8q ), aldehyde ( 8   l ), carboxylate ( 8   m, 8w ), ester ( 8o ), ketone ( 8   v ), and alkenyl ( 8w ), at the p , o , m -positions, were well-tolerated in the reaction. Significantly, this reaction also highlights the exceptional chemoselectivity of phenols compared to anilines ( 8k, 8t ) and alcohols ( 8j ). Regarding bisphenols ( 8z, 8aa, 8ag, 8ah ), the precise control of monosulfonate or bissulfonate formation is achievable by adjusting the amount of sulfonyl fluoride added. Moreover, in order to highlight the potential applicability of this synthetic protocol, fluorescein ( 8af ) and a selection of bioactive phenols, such as acetaminophen ( 8n ), triclosan ( 8ab ), vitamin E ( 8ac ), and estrone ( 8ae ) were subjected to the S-SuFEx reaction with 1b , resulting in the production of the desired products with excellent yields ranging from 81% to 99%. Additionally, the reaction between 1b and 4a using DCM/H 2 O (v/v, 4/1) as the solvent produced an 85% yield of 8a . Even when employing a PBS buffer solution (pH = 7.4) as the solvent for the reaction between 1b and 4a , a moderate yield of 48% was still achieved (see Supplementary Section  2.1.9 ).

Reaction conditions: alkyl sulfonyl fluoride 1b (0.3 mmol), phenol 4 (0.3 mmol), and BTMG (0.15 mmol) were stirred in MeCN (1 mL) for 2 h at room temperature. a Reaction run for 0.5 h. b With BTMG (0.3 mmol). c Phenol (0.15 mmol). d In DMF.

The S-SuFEx chemistry with aliphatic alcohols

The SuFEx reactions involving alkyl sulfonyl fluorides and alkyl alcohols present a more significant challenge than those with phenols, which have been notably elusive within the reported SuFEx chemistry. However, this investigation explored the compatibility of S-SuFEx chemistry with alcohols. Remarkably, the S-SuFEx reactions of 1b with various alcohols exhibited excellent reactivity (Fig.  5 ). Primary alcohols ( 10a–10d ) and more sterically hindered secondary alcohols ( 10e ) all gave excellent yields ranging from 72% to 97%. Notably, primary alcohols exhibited relatively higher reactivity compared to the more hindered secondary and tertiary alcohols (see Supplementary Section  7.8 ). Cyclic enols ( 10   f, 10i ) also reacted smoothly under the reaction conditions. The excellent chemoselectivity of S-SuFEx chemistry was once again exemplified by its remarkable tolerance of various functional groups ( 10c, 10e, 10   f ) and the distinct selectivity of alcohols over primary amines ( 10b ). In the case of amino alcohol 9b , only the target product 10b derived from the reaction between the hydroxyl group and sulfonyl fluoride was detected, with the remaining mass balance accounted for by the unreacted starting material.

Reaction conditions: alkyl sulfonyl fluoride 1b (0.3 mmol), aliphatic alcohol 9 (0.3 mmol) and BTMG (0.15 mmol) were stirred in MeCN (1 mL) for 6 h at room temperature. a Reaction run for 0.5 h.

The S-SuFEx chemistry with amines

N -nucleophiles constitute a wide spectrum of bioactive compounds. Harmonious with N -nucleophiles, click chemistry will offer substantial potential for the progression of functionalized materials and novel drugs. In contrast to the enduring challenges posed by conventional SuFEx chemistry when dealing with N -nucleophiles, particularly primary amines, our investigation revealed the remarkable efficacy of the innovative S-SuFEx chemistry in facilitating smooth reactions with primary, secondary, and cyclic amines, anilines, as well as diverse N -heteroaromatic compounds (Fig.  6 ). Generally, aliphatic amines showed higher reactivity compared to anilines, with secondary amines proving to be the most reactive N -nucleophiles in S-SuFEx chemistry. High yields were achieved with both linear ( 12a - 12c ) and cyclic ( 12d – 12i ) secondary amines. In the case of amino alcohol ( 12   f ), S-SuFEx chemistry exhibited higher selectivity toward cyclic secondary amines compared to secondary alcohols, resulting in a moderate yield of 64%. Although primary amines displayed slightly lower reactivity than secondary amines, the S-SuFEx reactions with primary amines, including sterically hindered primary amines ( 12k ) and benzyl amines ( 12l – 12q ), also gave high yields by extending the reaction time to 12 h. Anilines, while less nucleophilic than aliphatic amines, also proved effective in S-SuFEx chemistry when the reaction time was further extended to 24 h\. Anilines with electron-donating MeO- groups ( 12w ) yielded a perfect 94%, while anilines with electron-withdrawing groups ( 12x, 12   y ) resulted in slightly lower yields. Additionally, N -heteroaromatic compounds, such as pyrrole ( 12aa ), indoles ( 12ab ), imidazoles ( 12ad ) and benzimidazole ( 12ae ), also exhibited high compatibility with S-SuFEx chemistry. To further underscore the potential applications of S-SuFEx chemistry in constructing bioactive functionalized materials, we extended our testing to a series of drugs and pesticides, including amlodipine ( 12   v ), melatonin ( 12ac ), and carbendazim ( 12ae ). Remarkably, all of them yielded perfect sulfonylation products, with sensitive functional groups like ester and amide remaining entirely unaffected. These results demonstrate the potential of S-SuFEx chemistry for broad synthetic applications.

Reaction conditions: alkyl sulfonyl fluoride 1b (0.3 mmol), amine 11 (0.3 mmol), and BTMG (0.3 mmol) were stirred in MeCN (1 mL) for 12 h at room temperature. a Reaction run for 2 h. b Reaction run for 24 h. c With BTMG (0.15 mmol); Reaction run for 2 h.

Organic-inorganic linking via S-SuFEx click chemistry

Upon establishing the pronounced reactivity of the S-SuFEx click hub with various O , N- nucleophiles, we proceeded to apply click hub 1c for the creation of functionalized SAMs on the surface of inorganic materials via organic-inorganic linking. Glass slides were selected as the exemplar inorganic substrates. To prepare functionalized SAM, we initiated the process by coupling 1c with the selected organic compounds using S-SuFEx chemistry. Notably, 1c displayed a slightly higher reactivity than its analog 1b , reacting smoothly with phenols, alcohols, and amines in the presence of 0.2 equiv. BTMG. The reactions between 1c and the 15 tested substrates gave 76 – 99% yields (Fig.  7a ). In a typical approach for the preparation of SAM, the reaction mixture of 1c and organic compounds can be directly employed to react with the glass surface without the need for purification. Covalent linkage between the glass and selected organic compounds is achieved by simply immersing the glass slides in the hydrolysate of the reaction mixture for 24 h (Fig.  7b ). The hydrolyzed trialkoxy silane group effectively anchors the organic moiety onto the glass surface, forming SAMs. In this study, we examined the linkage of four representative organic compounds to the glass surface, namely, triclosan (TC), fluorescein (FR), 1 H ,1 H ,2 H ,2 H -perfluoro-1-decanol (PD), and nonylphenol (NP).

a SuFEx reactivity of the S-SuFEx hub 1c . Reaction conditions: alkyl sulfonyl fluoride 1c (0.3 mmol), 13 (0.3 mmol), and BTMG (0.06 mmol) were stirred in MeCN (1 mL) for 2 h at room temperature. b Preparation of functionalized SAM using 1c on the surface of inorganic material.

The glass slides linked with TC, FR, PD and NP displayed no significant changes in appearance, remaining colorless and transparent. However, the contact angles of water on their surfaces were markedly changed (Fig.  8 and Supplementary Fig.  8 ). Atomic force microscopy (AFM) analysis revealed that both the pristine slide and the TC linked slides exhibited a rough surface with irregularities and protuberances. The subsequent AFM-IR spectra provided further confirmation of the covalently linked TC molecules on the glass surfaces (Fig.  8b , c ). TC is a widely recognized antimicrobial agent. Covalently linking TC to the glass surface was expected to render it antibacterial. Indeed, the antibacterial tests confirmed that the SAM exhibited excellent antibacterial efficacy against Staphylococcus aureus , with a remarkable reduction in the counts of S. aureus , resulting in an antibacterial efficacy (R) of 4.59 (Fig.  9a and Supplementary Fig.  9 ). Furthermore, linking FR to the glass surface using the S-SuFEx hub 1c resulted in a glass surface with fluorescence, as confirmed by fluorescence microscope images (Fig.  9b and Fig. Supplementary Fig.  10 ). This provides an effective method for preparing inorganic materials with fluorescence labeling. Functionalizing the glass surface with PD and NP rendered it hydrophobic. The highest hydrophobicity of 98.5 degree was achieved with PD functionalized glass surfaces (Fig.  9c ). As expected, NP-functionalized glass surfaces also exhibited excellent antibacterial properties against S. aureus (Supplementary Fig.  9 ). Using FR-functionalized glass as the model, we tested the stability of this organic-inorganic linking system. The results indicated that the system exhibited excellent stability, with robust tolerance to acid (pH = 2) (Supplementary Fig.  11 ), high temperature (Supplementary Fig.  12 ) or flushing with organic solvents (Supplementary Fig.  13 ). However, the functionalized glass slides showed poor base tolerance, which was primarily caused by the dissolution of Si–O–Si network structure in a strong alkaline environment 55 . Furthermore, we specifically attempted to immobilize the peptide oxytocin on the glass surface using 1c (Supplementary Fig.  14 ). The successful outcomes of the peptide immobilization process suggested that this clickable platform may have significant application value in biological detection. In summary, the covalent linkage of various functional organic molecules and inorganic materials has been successfully established, showcasing the general versatility and simplicity of the organic-inorganic linking strategy using 1c . This approach generates a versatile platform for achieving any desired organic-inorganic linking.

a AFM image of the untreated glass slide. b AFM-IR image obtained at 1475 cm −1 of the triclosan-functionalized glass surface. c AFM-IR spectra obtained at untreated glass surface (CK), and triclosan-functionalized SAM on glass surface (TC).

a Antibacterial effect against S. aureus of the glass surface with triclosan-functionalized SAM. b Fluorescence imaging of the glass surface with fluorescein-functionalized SAM. The experiment was independently repeated three times with similar results. c Hydrophobicity of glass surface functionalized with 1 H ,1 H ,2 H ,2 H -perfluoro-1-decanol.

Mechanistic investigations

A series of experiments were conducted to elucidate the mechanism of S-SuFEx click chemistry, using the SuFEx reaction between 1b and phenol 4a as the model reaction. Initial investigations focused on the base’s role in this process, as illustrated in Fig.  10 . The absence of BTMG resulted in no observable reaction between 1b and 4a , underscoring the indispensable role of BTMG (Fig.  10a ). With BTMG present, two potential reaction mechanisms were considered. The first hypothesis suggests that the base deprotonates the α -position of 1b to form intermediate 15 , which then reacts with nucleophile 4a to yield the final product 8a through a deprotonation-elimination-addition mechanism, involving sulfene 16 as the reactive intermediate (Fig.  10d ). Alternatively, BTMG might first interact with 4a to produce deprotonated phenol 17 , which could then undergo an S N 2 reaction with 1b to form the final product (Fig.  10e ). To determine the prevailing mechanism, further experiments were conducted. Introduction of 0.5 equiv. of BTMG to 1b in MeCN- d 3 revealed partial deprotonation at the α -position to give 15 through 1 H NMR analysis (Fig.  10b and Supplementary Fig.  16 ), yet without evidence of S-F bond dissociation according to the 19 F NMR (Fig.  10c ), indicating the absence of sulfene 16 formation. Further adding 1.0 equiv. of phenol 4a to the deprotonated alkyl sulfonyl fluoride 15 and stirring for 2 hours led to no detectable product 8a , suggesting the reaction between alkyl sulfonyl fluorides and BTMG was a non-productive side pathway. Conversely, introducing BTMG to a MeCN- d 3 solution of 4a induced a significant upfield shift in the aromatic region of the 1 H NMR spectrum (Supplementary Fig.  17 ), indicative of the formation of 17 5 . Addition of 1b to the solution of 17 resulted in a quantitative yield of the product 8a (Fig.  10b ), strongly supporting the S N 2 pathway between 1b and 17 as the primary reaction route. Considering the high yields achieved with most substrates, it is hypothesized that the side reaction between 1b and BTMG progresses much more slowly than the favorable S N 2 reaction.

a 1 H NMR spectra for the reaction between 1b and 4a with or without BTMG (500 MHz, MeCN- d 3 ). b 1 H NMR spectra for the control reaction (500 MHz, MeCN- d 3 ). c 19 F NMR spectra for the reaction between BTMG and 1b (500 MHz, MeCN- d 3 ). d Proposed mechanism disproved by experiments. e Proposed mechanism. f Electrostatic potential map of 1b . Red = electron excess and blue = electron deficiency. g The S···F distance of 1b is 3.11 Å, falling into the range of chalcogen bonding distance. The E (2) is the second order perturbation stabilization energy. h Role of phenoxide guanidinium complex in the S-SuFEx process. i Further expansion of the S-SuFEx chemistry.

Despite the generally slow S N 2 reactions observed with most alkyl sulfonyl fluorides, we propose that the presence of an intramolecular ChB could significantly increase the electrophilicity of 1b , thereby enhancing its reactivity towards nucleophiles. To validate our hypothesis, we undertook computational studies. The initial step involved determining the conformation of 1b using DFT computations at the M062X/6-311 G(d,p) level. Our findings indicated that the gauche conformation of 1b is only marginally less stable than its anti counterpart, with a free energy barrier of approximately 1.0 kcal/mol between them (Supplementary Fig.  18 ). This barrier is sufficiently low to allow for easy interconversion between these conformations at room temperature. Further analysis was focused on the electrostatic potential map of the gauche conformation (Fig.  10f ), revealing distinct electrostatic interactions between the negatively charged fluorine and the positively charged sulfur atoms. We further computationally measured the distance and strength of the ChB between S and F in 1b using NBO analysis. The measured distance was 3.11 Å, which is less than the sum of their van der Waals radii (∑ r vdW (S···F) = 3.27 Å) 56 . The strength of this interaction was measured to be 5.37 kcal/mol (Fig.  10g ). These computational insights strongly advocate for the existence of an intramolecular ChB between sulfur and fluorine in the gauche conformation. The ChB will make the fluorine a better leaving group and thus accelerating the S-SuFEx chemistry.

Furthermore, inspired by the discovery of BTMG as an exceptional SuFEx catalyst by Moses et al. 5 , we hypothesized that the phenoxide guanidinium complex 17 might also facilitate sulfonyl fluoride group activation via hydrogen bonding with fluorine. Empirical validation involved direct interaction of 1b with sodium phenoxide 4a’ , achieving an impressive 87% yield of 8a (Fig.  10h , Eq. 9 ), albeit slightly lower than the 99% yield obtained with 4a and BTMG (Fig.  10h , Eq. 3 ). Conversely, the reaction of 3b with sodium phenoxide yielded a mere 31% of 8a (Fig.  10h , Eq. 10 ), underscoring the intramolecular ChB as the predominant factor in alkyl sulfonyl fluoride activation, with the phenoxide guanidinium complex playing a supportive role in this activation process.

Given the established activation of alkyl sulfonyl fluorides through non-bonding 1,5-S···F interactions, we explored the possibility of achieving a similar activation effect via 1,6-S···F interactions. Accordingly, we synthesized compound 18 , using 1-propanethiol, and 2-propene-1-sulfonyl fluoride as precursors and 2,2’-azobis(2-methylpropionitrile) as the reagent. The reaction between 18 and 4a , in the presence of 0.5 equiv. of BTMG, gave an exceptional 99% yield of 19 within 0.5 h (Fig.  7i , Eq. 11 ), demonstrating the feasibility of ChB activation by 1,6-S···F interactions. The Markovnikov addition product 20 and 4a also exhibited high reactivity towards nucleophile 4a , achieving a 99% yield using 0.5 equiv. of BTMG within 0.5 h (Fig.  10i , Eq. 12 ). Furthermore, the reactivity of phenyl fluorosulfonate could also be moderately enhanced by a 2-thio group via a 1,6-S···F interaction (see Supplementary Section  3.7 ). These outcomes collectively underscore the broader applicability of the intramolecular ChB-activated S-SuFEx reaction, demonstrating its potential for diverse synthetic applications.

In summary, we present the intramolecular SuFExability activation strategy of alkyl sulfonyl fluorides using γ-S atom. The introduction of γ-S may take advantage of intramolecular chalcogen bonding to active sulfonyl fluoride unit and facilitate attack of O , N -nucleophiles. The activated SuFEx reactivity of alkyl sulfonyl fluorides is achieved with relatively low base loadings under mild and simple conditions while circumventing the need to prepare silyl-ether substrates or additional stoichiometric activators/additives. Thus, we realize the efficient SuFEx process between alkyl sulfonyl fluorides and O , N -nucleophiles with great abundance and structural diversity. This intramolecular activation strategy offers a potentially general and practically sustainable approach for straightforward transformation to useful molecules, which is a valuable addition to the synthetic toolkit. Significantly, the S-SuFEx hub 1c , which incorporates a trialkoxy silane group, has been established as a universal clickable platform for the highly efficient covalent linkage of organic compounds and inorganic materials. Its application was showcased in creating SAMs that impart glass surfaces with antibacterial activity, hydrophobicity, and fluorescence. In our ongoing investigation into the potential applications of S-SuFEx chemistry, we will focus on an in-depth examination of utilizing ESF as a linking agent for the efficient coupling of thiols with O- and N -nucleophiles. The strategy reported herein may open a new avenue in SuFEx chemistries.

Synthesis of alkyl sulfonyl fluorides bearing γ-S

A 50 mL round bottom flask was charged with ESF (2.2 g, 20 mmol), thiol (20 mmol, 1.0 equiv.) in THF (20 mL), then added triethylamine (0.1 g, 1 mmol) dropwise. The reaction mixture was stirred at room temperature for 3 h. After completion of the reaction, the solvent was removed directly under reduced pressure. The crude product was purified by a flash column chromatography eluted with petroleum ether PE/EA to afford the products 2-(thiol)ethane-1-sulfonyl fluoride 1 .

General procedure for the sulfonylation with O, N -nucleophiles

A 10 mL round bottom flask was charged with 1 (0.3 mmol, 1 equiv.), O , N -nucleophile (0.3 mmol, 1 equiv.) in MeCN (1 mL), then added BTMG (0.5 equiv.). The reaction mixture was stirred at room temperature. When the reaction was completed, the solvent was concentrated in vacuo. The residue was purified via a flash chromatography to afford the pure product.

General procedure for covalently linking organic compounds and inorganic materials

A 10 mL round bottom flask was charged with 1c (0.3 mmol, 1 equiv.), 13 (0.3 mmol, 1 equiv.) in anhydrous MeCN (1 mL), then added BTMG (0.06 mmol, 0.2 equiv.). The reaction mixture was stirred at room temperature for 2 h. When the reaction was completed, 100 μL of reaction mixture was added to the hydrolysate (EtOH/H 2 O, 10:1 v/v, 10 mL), and the pH was adjusted to 4.0 by acetic acid. Subsequently, the hydroxylated glass substrates were immersed to the solution and incubated for 24 h at room temperature. The treated cover slides were sonicated for 10 min in deionized water and then in acetone, ethanol and dried under the Ar flow.

Reporting summary

Further information on research design is available in the  Nature Portfolio Reporting Summary linked to this article.

Data availability

Experimental data as well as characterization data for all new compounds prepared in the course of these studies are provided in the Supplementary Information. The data supporting the findings of this study are available within the main text and the supplementary information. Source data are provided in this paper. All data are available from the corresponding author upon request.  Source data are provided with this paper.

Kolb, H. C., Finn, M. G. & Sharpless, K. B. Click chemistry: diverse chemical function from a few good reactions. Angew. Chem. Int. Ed. 40 , 2004–2021 (2001).

Article   CAS   Google Scholar  

Finn, M. G., Kolb, H. C. & Sharpless, K. B. Click chemistry connections for functional discovery. Nat. Synth. 1 , 8–10 (2022).

Article   ADS   Google Scholar  

Dong, J., Krasnova, L., Finn, M. G. & Sharpless, K. B. Sulfur(VI) fluoride exchange (SuFEx): another good reaction for click chemistry. Angew. Chem. Int. Ed. 53 , 9430–9448 (2014).

Lou, T. S. B. & Willis, M. C. Sulfonyl fluorides as targets and substrates in the development of new synthetic methods. Nat. Rev. Chem. 6 , 146–162 (2022).

Article   CAS   PubMed   Google Scholar  

Smedley, C. J. et al. Accelerated SuFEx click chemistry for modular synthesis. Angew. Chem. Int. Ed. 61 , e202112375 (2022).

Article   ADS   CAS   Google Scholar  

Wei, M. et al. A broad-spectrum catalytic amidation of sulfonyl fluorides and fluorosulfates. Angew. Chem. Int. Ed. 60 , 7397–7404 (2021).

Li, S., Wu, P., Moses, J. E. & Sharpless, K. B. Multidimensional suFEx click chemistry: sequential sulfur(VI) fluoride exchange connections of diverse modules launched from an SOF 4 hub. Angew. Chem. Int. Ed. 56 , 2903–2908 (2017).

Smedley, C. J. et al. 1-Bromoethene-1-sulfonyl fluoride (BESF) is another good connective hub for SuFEx click chemistry. Chem. Commun. 54 , 6020–6023 (2018).

Guo, T. et al. A new portal to SuFEx click chemistry: a stable fluorosulfuryl imidazolium salt emerging as an “F-SO2 +” donor of unprecedented reactivity, selectivity, and scope. Angew. Chem. Int. Ed. 57 , 2605–2610 (2018).

Smedley, C. J. et al. Diversity oriented clicking (DOC): divergent synthesis of SuFExable pharmacophores from 2-substituted-alkynyl-1-sulfonyl fluoride (SASF) hubs. Angew. Chem. Int. Ed. 59 , 12460–12469 (2020).

Sun, S., Gao, B., Chen, J., Sharpless, K. B. & Dong, J. Fluorosulfuryl Isocyanate Enabled SuFEx Ligation of Alcohols and Amines. Angew. Chem. Int. Ed. 60 , 21195–21199 (2021).

Li, B. Y. et al. Ex situ generation of thiazyl trifluoride (NSF 3 ) as a gaseous SuFEx hub. Angew. Chem. Int. Ed. 62 , e202305093 (2023).

Smedley, C. J., Giel, M. C., Fallon, T. & Moses, J. E. Ethene-1,1-disulfonyl difluoride (EDSF) for SuFEx click chemistry: synthesis of SuFExable 1,1-bissulfonylfluoride substituted cyclobutene hubs. Angew. Chem. Int. Ed. 62 , e202303916 (2023).

Wang, P., Zhang, H., Nie, X., Xu, T. & Liao, S. Photoredox catalytic radical fluorosulfonylation of olefins enabled by a bench-stable redox-active fluorosulfonyl radical precursor. Nat. Commun. 13 , 3370 (2022).

Article   ADS   CAS   PubMed   PubMed Central   Google Scholar  

Zeng, D., Deng, W. P. & Jiang, X. Advances in the construction of diverse SuFEx linkers. Natl. Sci. Rev. 10 , nwad123 (2023).

Homer, J. A. et al. Sulfur fluoride exchange. Nat. Rev. Methods Primers 3 , 58 (2023).

Article   CAS   PubMed   PubMed Central   Google Scholar  

Barrow, A. S. et al. The growing applications of SuFEx click chemistry. Chem. Soc. Rev. 48 , 4731–4758 (2019).

Lee, C. et al. The emerging applications of sulfur(VI) fluorides in catalysis. ACS Catal 11 , 6578–6589 (2021).

Nielsen, M. K., Ugaz, C. R., Li, W. & Doyle, A. G. PyFluor: a Low-cost, stable, and selective deoxyfluorination reagent. J. Am. Chem. Soc. 137 , 9571–9574 (2015).

Nielsen, M. K., Ahneman, D. T., Riera, O. & Doyle, A. G. Deoxyfluorination with sulfonyl fluorides: navigating reaction space with machine learning. J. Am. Chem. Soc. 140 , 5004–5008 (2018).

Meng, G. et al. Modular click chemistry libraries for functional screens using a diazotizing reagent. Nature 574 , 86–89 (2019).

Article   ADS   CAS   PubMed   Google Scholar  

Brighty, G. J. et al. Using sulfuramidimidoyl fluorides that undergo sulfur(VI) fluoride exchange for inverse drug discovery. Nat. Chem. 12 , 906–913 (2020).

Cheng, Y. et al. Diversity oriented clicking delivers β-substituted alkenyl sulfonyl fluorides as covalent human neutrophil elastase inhibitors. Proc. Natl. Acad. Sci. 119 , e2208540119 (2022).

Article   PubMed   PubMed Central   Google Scholar  

Zhao, Q. et al. Broad-spectrum kinase profiling in live cells with lysine-targeted sulfonyl fluoride probes. J. Am. Chem. Soc 139 , 680–685 (2017).

Liu, F. et al. Biocompatible SuFEx click chemistry: thionyl tetrafluoride (SOF 4 )-derived connective hubs for bioconjugation to DNA and proteins. Angew. Chem. Int. Ed. 58 , 8029–8033 (2019).

Li, S. et al. SuFExable polymers with helical structures derived from thionyl tetrafluoride. Nat. Chem. 13 , 858–867 (2021).

Subramaniam, M., Ruggeri, F. S. & Zuilhof, H. Degradable click-reaction-based polymers as highly functional materials. Matter 5 , 2490–2492 (2022).

Li, H. et al. High-performing polysulfate dielectrics for electrostatic energy storage under harsh conditions. Joule 7 , 95–111 (2023).

Liang, D. D. et al. Silicon-free SuFEx reactions of sulfonimidoyl fluorides: scope, enantioselectivity, and mechanism. Angew. Chem. Int. Ed. 59 , 7494–7500 (2020).

Gao, B. et al. Bifluoride-catalysed sulfur(VI) fluoride exchange reaction for the synthesis of polysulfates and polysulfonates. Nat. Chem. 9 , 1083–1088 (2017).

Mukherjee, P. et al. Sulfonamide synthesis via calcium triflimide activation of sulfonyl fluorides. Org. Lett. 20 , 3943–3947 (2018).

Shirota, Y., Nagai, T. & Tokura, N. Reactions of alkanesulphonic acid derivatives with organoalkali metal compounds: formation and reactivity of α-sulphonylcarbanions. Tetrahedron 25 , 3193–3204 (1969).

Gutiérrez López, M. Á., Tan, M. L., Frontera, A. & Matile, S. The origin of anion-π autocatalysis. JACS Au 3 , 1039–1051 (2023).

Banik, S. M., Levina, A., Hyde, A. M. & Jacobsen, E. N. Lewis acid enhancement by hydrogen-bond donors for asymmetric catalysis. Science 358 , 761–764 (2017).

Sutar, R. L. & Huber, S. M. Catalysis of organic reactions through halogen bonding. ACS Catal 9 , 9622–9639 (2019).

Wonner, P., Dreger, A., Vogel, L., Engelage, E. & Huber, S. M. Chalcogen bonding catalysis of a nitro-michael reaction. Angew. Chem. Int. Ed. 58 , 16923–16927 (2019).

Liu, J., Zhou, M., Deng, R., Zheng, P. & Chi, Y. R. Chalcogen bond-guided conformational isomerization enables catalytic dynamic kinetic resolution of sulfoxides. Nat. Commun. 13 , 4793 (2022).

Zhu, H., Zhou, P. P. & Wang, Y. Cooperative chalcogen bonding interactions in confined sites activate aziridines. Nat. Commun. 13 , 3563 (2022).

Bitai, J., Nimmo, A. J., Slawin, A. M. Z. & Smith, A. D. Cooperative palladium/isothiourea catalyzed enantioselective formal (3+2) cycloaddition of vinylcyclopropanes and α,β-unsaturated esters. Angew. Chem. Int. Ed. 61 , e202202621 (2022).

Lu, Y., Liu, Q., Wang, Z. X. & Chen, X. Y. Alkynyl sulfonium salts can be employed as chalcogen-bonding catalysts and generate alkynyl radicals under blue-light irradiation. Angew. Chem. Int. Ed. 61 , e202116071 (2022).

Benz, S. et al. Catalysis with chalcogen bonds. Angew. Chem. Int. Ed. 56 , 812–815 (2017).

Vogel, L., Wonner, P. & Huber, S. M. Chalcogen bonding: an overview. Angew. Chem. Int. Ed. 58 , 1880–1891 (2019).

Pascoe, D. J., Ling, K. B. & Cockroft, S. L. The origin of chalcogen-bonding interactions. J. Am. Chem. Soc. 139 , 15160–15167 (2017).

Beno, B. R., Yeung, K. S., Bartberger, M. D., Pennington, L. D. & Meanwell, N. A. A survey of the role of noncovalent sulfur interactions in drug design. J. Med. Chem. 58 , 4383–4438 (2015).

Werz, D. B. et al. Self-organization of chalcogen-containing cyclic alkynes and alkenes to yield columnar structures. Org. Lett. 4 , 339–342 (2002).

Gleiter, R., Haberhauer, G., Werz, D. B., Rominger, F. & Bleiholder, C. From noncovalent chalcogen-chalcogen interactions to supramolecular aggregates: experiments and calculations. Chem. Rev. 118 , 2010–2041 (2018).

Biot, N. & Bonifazi, D. Chalcogen-bond driven molecular recognition at work. Coord. Chem. Rev. 413 , 213243 (2020).

Wang, W. et al. Chalcogen-chalcogen bonding catalysis enables assembly of discrete molecules. J. Am. Chem. Soc. 141 , 9175–9179 (2019).

He, X. et al. Bis-selenonium cations as bidentate chalcogen bond donors in catalysis. ACS Catal 11 , 12632–12642 (2021).

Zhang, Q., Chan, Y. Y., Zhang, M., Yeung, Y. Y. & Ke, Z. Hypervalent chalcogenonium···π bonding catalysis. Angew. Chem. Int. Ed. 61 , e202208009 (2022).

Al Zoubi, W. et al. Recent advances in hybrid organic-inorganic materials with spatial architecture for state-of-the-art applications. Prog. Mater. Sci. 112 , 100663 (2020).

Zhou, C. et al. Hybrid organic-inorganic two-dimensional metal carbide MXenes with amido- and imido-terminated surfaces. Nat. Chem. 15 , 1722–1729 (2023).

Young, C. M. et al. The importance of 1,5-oxygen···chalcogen interactions in enantioselective isochalcogenourea catalysis. Angew. Chem. Int. Ed. 59 , 3705–3710 (2020).

Wang, L., Schubert, U. S. & Hoeppener, S. Surface chemical reactions on self-assembled silane based monolayers. Chem. Soc. Rev. 50 , 6507–6540 (2021).

Dove, P. M., Han, N., Wallace, A. F. & De Yoreo, J. J. Kinetics of amorphous silica dissolution and the paradox of the silica polymorphs. Proc. Natl. Acad. Sci. 105 , 9903–9908 (2008).

Ho, P. C., Wang, J. Z., Meloni, F. & Vargas-Baca, I. Chalcogen bonding in materials chemistry. Coordin. Chem. Rev. 422 , 213464 (2020).

Download references

Acknowledgements

This work was financially supported by the National Key Research and Development Program of China (2022YFF0710402, J.A.).

Author information

Authors and affiliations.

Key Laboratory of Precision Nutrition and Food Quality, Department of Nutrition and Health, China Agricultural University, Beijing, 100193, China

Minlong Wang, Jiaman Hou, Chao Wang, Xiaohe Zhang, Ying Du, Qixin Dong, Lijun Wang, Ke Ni, Fazheng Ren & Jie An

Department of Chemical and Environmental Engineering, University of Nottingham Ningbo China, Ningbo, 315100, China

You can also search for this author in PubMed   Google Scholar

Contributions

J.A. and M.W. designed the experiments. J.A. and F.R. directed the project. M.W., J.H., C.W., Q.D. and X.Z. conducted the experiments. H.D. performed the DFT calculations. M.W., H.D., Y.D., C.W., L.W. and K.N. contributed to the data analysis and visualization. J.A. and M.W. prepared the paper with contribution from all authors.

Corresponding author

Correspondence to Jie An .

Ethics declarations

Competing interests.

The authors declare no competing interests.

Peer review

Peer review information.

Nature Communications thanks Jianguo Lin and the other anonymous reviewer(s) for their contribution to the peer review of this work. A peer review file is available.

Additional information

Publisher’s note Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary information

Supplementary information, peer review file, reporting summary, source data, source data, rights and permissions.

Open Access This article is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License, which permits any non-commercial use, sharing, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if you modified the licensed material. You do not have permission under this licence to share adapted material derived from this article or parts of it. The images or other third party material in this article are included in the article’s Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by-nc-nd/4.0/ .

Reprints and permissions

About this article

Cite this article.

Wang, M., Hou, J., Do, H. et al. Intramolecular chalcogen bonding activated SuFEx click chemistry for efficient organic-inorganic linking. Nat Commun 15 , 6849 (2024). https://doi.org/10.1038/s41467-024-50922-9

Download citation

Received : 29 November 2023

Accepted : 25 July 2024

Published : 10 August 2024

DOI : https://doi.org/10.1038/s41467-024-50922-9

Share this article

Anyone you share the following link with will be able to read this content:

Sorry, a shareable link is not currently available for this article.

Provided by the Springer Nature SharedIt content-sharing initiative

By submitting a comment you agree to abide by our Terms and Community Guidelines . If you find something abusive or that does not comply with our terms or guidelines please flag it as inappropriate.

Quick links

• Explore articles by subject
• Guide to authors
• Editorial policies

Sign up for the Nature Briefing newsletter — what matters in science, free to your inbox daily.

• Exploring Inorganic Chemistry Through Real-World Scenarios | Chemistry Assignment Help

Real-World Case Studies in Inorganic Chemistry

Medicine's Platinum-Based Anticancer Drugs: Inorganic Chemistry:

Particularly in the field of cancer treatment, inorganic compounds have made significant advancements. The use of platinum-based medications like cisplatin, carboplatin, and oxaliplatin is a well-known example. These substances have been shown to be effective in chemotherapy treatments for a number of cancers, including colorectal, ovarian, and testicular cancer.

These medications' effectiveness is attributed to their capacity to bind to the DNA of cancer cells, prevent those cells from proliferating, and ultimately cause cell death. For instance, cisplatin inhibits transcription and replication by altering the structure of the DNA by creating intrastrand cross-links.

The mechanism of action of these medications and their side effects may be examined in a project based on this case study. It might also entail investigating recent studies designed to increase these drugs' efficacy or lessen their side effects. This could entail looking into other metal-based medications, comprehending their benefits and drawbacks, and considering how these medications can be enhanced using the concepts of inorganic chemistry assignment .

Hydrogen Fuel Cells and Inorganic Chemistry in Energy Production:

Different energy production technologies, such as the creation and use of hydrogen fuel cells, depend on inorganic chemistry. The functionality of these cells, which transform the chemical energy of hydrogen into electricity, depends on a number of inorganic compounds.

At the anode, which is frequently made of platinum, hydrogen gas (H2) is split into protons (H+) and electrons (e-) in a hydrogen fuel cell. The electrons are compelled to move through an external circuit, creating an electric current, while the protons proceed through a proton exchange membrane. Inorganic catalysts make it possible for oxygen (O2) from the air to combine with protons and electrons at the cathode (often made of platinum or another catalyst) to create water (H2O).

Researching the operation of hydrogen fuel cells and their function in the development of a sustainable energy future may be the subject of a chemistry assignment  related to this case study. This could entail looking into the various fuel cell components' material options, the difficulties associated with storing and transporting hydrogen, and the ongoing efforts to increase the effectiveness and affordability of these cells.

Industrial Inorganic Chemistry: The Haber-Bosch Process for Ammonia Synthesis

Processes used in industry, especially those that produce important chemicals, heavily rely on inorganic chemistry. A well-known example is the Haber-Bosch process, which creates ammonia (NH3) from nitrogen (N2) and hydrogen (H2).

Iron serves as a catalyst in the Haber-Bosch process, which uses high pressure and heat to help turn nitrogen and hydrogen into ammonia. The ammonia produced from this inorganic chemical reaction, a crucial component in the production of fertilizers and a key factor in raising agricultural productivity, has had a significant impact on the world.

The chemistry underlying the Haber-Bosch process, including the function of the iron catalyst and the conditions necessary for the reaction to happen, could be examined as part of a case study-related assignment. It could also entail investigating potential alternate processes for producing ammonia as well as researching the environmental effects of this process, particularly the energy use and CO2 emissions connected with it.

Lithium-Ion Batteries and Inorganic Chemistry in Battery Technology

The creation of effective and dependable energy storage systems is becoming more and more important as society moves toward renewable energy sources. Here, inorganic chemistry is essential, especially for the development and use of lithium-ion batteries.

Anode (typically made of graphite), cathode (typically a lithium metal oxide), and electrolyte (a lithium salt in an organic solvent) are the three main parts of a lithium-ion battery. Lithium ions move through the electrolyte from the anode to the cathode during the discharge of the battery, while electrons move through the external circuit to power devices. During charging, the process is turned around.

Examining the nuances of lithium-ion battery operation, the selection of materials for the anode, cathode, and electrolyte, as well as the difficulties associated with the life cycle, efficiency, and safety of these batteries, are possible assignments related to this case study. Students could also research new battery technologies, such as sodium-ion, solid-state, and lithium-sulfur batteries, and contrast their potential benefits and drawbacks with those of lithium-ion batteries.

The Chemistry of CFCs and Ozone Depletion in Inorganic Chemistry and the Ozone Layer

We can better understand and address important environmental problems like the ozone layer depletion thanks to inorganic chemistry. CFCs, which were once commonly used in aerosols and refrigerants, are a major factor in this phenomenon.

When CFCs are released into the atmosphere, a problem occurs. They gradually ascend to the stratosphere, where solar radiation breaks them down, releasing chlorine atoms. These chlorine atoms can catalyze a reaction that turns ozone (O3) into molecular oxygen (O2) by destroying ozone (O3). This process lowers the stratospheric ozone concentration, resulting in the development of the infamous "ozone hole."

A project based on this case study might investigate the chemical interactions between CFCs and ozone in the stratosphere. Additionally, it could explore the effects of ozone depletion on the environment and the steps taken to mitigate this issue, like the Montreal Protocol. To further emphasize how inorganic chemistry contributes to the design of environmentally friendly materials, the development of CFC substitutes could be investigated.

Carbon dating and inorganic chemistry in archaeology:

Through methods like carbon dating, inorganic chemistry also plays a critical role in areas like archaeology. The age of ancient artifacts and fossils can be ascertained by scientists using carbon dating, also known as radiocarbon dating.

Living things absorb carbon-14, a radioactive isotope that is produced in the atmosphere by cosmic radiation. When a living thing passes away, it stops absorbing carbon-14, which then starts to degrade at a predetermined rate. The amount of Carbon-14 still present in a sample and that of a living organism can be compared to determine how long it has been since the organism died.

Understanding the underlying concepts and procedures of carbon dating, its uses and restrictions, and the function of inorganic chemistry in this and other dating techniques may be part of an assignment on this case study. This could go even further and look at how carbon dating has helped us understand human history and evolution, as well as how it has been used in other disciplines like geology and climatology.

Conclusion:

There is more to inorganic chemistry than just textbooks. These case studies show how it supports a wide range of real-world scenarios. It has the potential to address a number of global issues, including medical conditions, energy production, and industrial applications as well as environmental degradation. Students gain a deeper understanding of inorganic chemistry concepts as well as an appreciation of their practical relevance and potential impact on our world by examining these real-world scenarios through assignments.

Post a comment...

Exploring inorganic chemistry through real-world scenarios | chemistry assignment help submit your assignment, attached files.

• StudentHome
• IntranetHome
• SponsorHome
• Contact the OU
• Accessibility
• Postgraduate
• News & media
• Business & apprenticeships

• Collections
• OU Study Materials
• Module S247

Inorganic chemistry :concepts and case studies

Related Archive Content

The Open University

• Conditions of use
• Privacy and cookies
• Modern Slavery Act (pdf 149kb)

© 2021 . All rights reserved. The Open University is incorporated by Royal Charter (RC 000391), an exempt charity in England & Wales and a charity registered in Scotland (SC 038302). The Open University is authorised and regulated by the Financial Conduct Authority in relation to its secondary activity of credit broking.

• © Copyright
• +44 (0) 845 300 60 90

Journal of Materials Chemistry A

Spin texture evolution of rashba splitting under pressure: a case study of inorganic nitride perovskite crystal.

Spin-orbit coupling (SOC) effects in non-centrosymmetric systems lead to a uniform spin configuration in momentum space known as persistent spin texture (PST). The PST has been predicted to support an extraordinarily long spin lifetime of carriers promising for spintronics applications. Using density functional theory, we report the existence of PST in nitrogen-based perovskite (CeTaN 3 ), a non-centrosymmetric ferroelectric material with spontaneous polarization of 5.6 μC/cm 2 along [100] direction. Our calculations showed that CeTaN 3 is a direct band gap (0.436 eV) semiconductor and exhibits PST both in the conduction and valence bands. The calculated Rashba parameter was 0.399 eVÅ (0.282 eVÅ) for the conduction (valence) band. A comprehensive investigation of the stability of CeTaN 3 was performed by calculating its elastic constants, reaction decomposition enthalpy, and phonon dispersion. All three methods showed that CeTaN 3 is stable. We also investigated the effects of the hydrostatic pressure on the spin splitting of the bands. We found that CeTaN 3 preserved the PST up to 6 GPa and the splitting of the bands disappeared at 8 GPa. The present study paves the way for using external pressure as a prime factor in tuning not-yet-synthesized perovskite materials suitable for spintronics and optoelectronic applications.

Supplementary files

• Supplementary information PDF (1406K)

Article information

Download citation, permissions.

S. Mir and S. Chakraborty, J. Mater. Chem. A , 2024, Accepted Manuscript , DOI: 10.1039/D4TA02555E

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page .

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page .

Read more about how to correctly acknowledge RSC content .

Social activity

Search articles by author.

This article has not yet been cited.

Inorganic Chemistry: Concepts and Case Studies: Study Units: Case Study 3: Molecules in Space (Inorganic Chemistry: Concepts and Case Studies)

By e. moore and h. kroto.

• 0 Want to read
• 0 Currently reading
• 0 Have read

Inorganic Chemistry: Concepts and Case Studies: Study Units: Case Stud ...

My Reading Lists:

Use this Work

Create a new list

My book notes.

My private notes about this edition:

Check nearby libraries

• Library.link

Buy this book

This edition doesn't have a description yet. Can you add one ?

Showing 1 featured edition. View all 1 editions?

Add another edition?

Book Details

The physical object, source records, community reviews (0).

• Created April 30, 2008
• 5 revisions

Wikipedia citation

Copy and paste this code into your Wikipedia page. Need help?

• Science & Math

Sorry, there was a problem.

Download the free Kindle app and start reading Kindle books instantly on your smartphone, tablet, or computer - no Kindle device required .

Read instantly on your browser with Kindle for Web.

Using your mobile phone camera - scan the code below and download the Kindle app.

Image Unavailable

• To view this video download Flash Player

Inorganic Chemistry: Case Studies 1-4: Concepts and Case Studies (Course S247) Paperback – January 1, 1982

• Print length 76 pages
• Language English
• Publisher Open UP
• Publication date January 1, 1982
• ISBN-10 0335170277
• ISBN-13 978-0335170272
• See all details

Product details

• Publisher ‏ : ‎ Open UP (January 1, 1982)
• Language ‏ : ‎ English
• Paperback ‏ : ‎ 76 pages
• ISBN-10 ‏ : ‎ 0335170277
• ISBN-13 ‏ : ‎ 978-0335170272
• Item Weight ‏ : ‎ 1.11 pounds

Customer reviews

• 5 star 4 star 3 star 2 star 1 star 5 star 0% 0% 0% 0% 0% 0%
• 5 star 4 star 3 star 2 star 1 star 4 star 0% 0% 0% 0% 0% 0%
• 5 star 4 star 3 star 2 star 1 star 3 star 0% 0% 0% 0% 0% 0%
• 5 star 4 star 3 star 2 star 1 star 2 star 0% 0% 0% 0% 0% 0%
• 5 star 4 star 3 star 2 star 1 star 1 star 0% 0% 0% 0% 0% 0%

Customer Reviews, including Product Star Ratings help customers to learn more about the product and decide whether it is the right product for them.

To calculate the overall star rating and percentage breakdown by star, we don’t use a simple average. Instead, our system considers things like how recent a review is and if the reviewer bought the item on Amazon. It also analyzed reviews to verify trustworthiness.

No customer reviews

• About Amazon
• Investor Relations
• Amazon Devices
• Amazon Science
• Sell products on Amazon
• Sell on Amazon Business
• Sell apps on Amazon
• Become an Affiliate
• Advertise Your Products
• Self-Publish with Us
• Host an Amazon Hub
• › See More Make Money with Us
• Amazon Business Card
• Shop with Points
• Reload Your Balance
• Amazon Currency Converter
• Amazon and COVID-19
• Your Account
• Your Orders
• Shipping Rates & Policies
• Returns & Replacements
• Manage Your Content and Devices

• Conditions of Use
• Privacy Notice
• Consumer Health Data Privacy Disclosure
• Your Ads Privacy Choices

Information

• Author Services

Initiatives

You are accessing a machine-readable page. In order to be human-readable, please install an RSS reader.

All articles published by MDPI are made immediately available worldwide under an open access license. No special permission is required to reuse all or part of the article published by MDPI, including figures and tables. For articles published under an open access Creative Common CC BY license, any part of the article may be reused without permission provided that the original article is clearly cited. For more information, please refer to https://www.mdpi.com/openaccess .

Feature papers represent the most advanced research with significant potential for high impact in the field. A Feature Paper should be a substantial original Article that involves several techniques or approaches, provides an outlook for future research directions and describes possible research applications.

Feature papers are submitted upon individual invitation or recommendation by the scientific editors and must receive positive feedback from the reviewers.

Editor’s Choice articles are based on recommendations by the scientific editors of MDPI journals from around the world. Editors select a small number of articles recently published in the journal that they believe will be particularly interesting to readers, or important in the respective research area. The aim is to provide a snapshot of some of the most exciting work published in the various research areas of the journal.

Original Submission Date Received: .

• Active Journals
• Find a Journal
• Proceedings Series
• For Authors
• For Reviewers
• For Editors
• For Librarians
• For Publishers
• For Societies
• For Conference Organizers
• Open Access Policy
• Institutional Open Access Program
• Special Issues Guidelines
• Editorial Process
• Research and Publication Ethics
• Article Processing Charges
• Testimonials
• Preprints.org
• SciProfiles
• Encyclopedia

Article Menu

• Subscribe SciFeed
• Recommended Articles
• Google Scholar
• on Google Scholar
• Table of Contents

Find support for a specific problem in the support section of our website.

Please let us know what you think of our products and services.

Visit our dedicated information section to learn more about MDPI.

JSmol Viewer

Predicting coastal water quality with machine learning, a case study of beibu gulf, china.

Share and Cite

Bai, Y.; Xu, Z.; Lan, W.; Peng, X.; Deng, Y.; Chen, Z.; Xu, H.; Wang, Z.; Xu, H.; Chen, X.; et al. Predicting Coastal Water Quality with Machine Learning, A Case Study of Beibu Gulf, China. Water 2024 , 16 , 2253. https://doi.org/10.3390/w16162253

Bai Y, Xu Z, Lan W, Peng X, Deng Y, Chen Z, Xu H, Wang Z, Xu H, Chen X, et al. Predicting Coastal Water Quality with Machine Learning, A Case Study of Beibu Gulf, China. Water . 2024; 16(16):2253. https://doi.org/10.3390/w16162253

Bai, Yucai, Zhefeng Xu, Wenlu Lan, Xiaoyan Peng, Yan Deng, Zhibiao Chen, Hao Xu, Zhijian Wang, Hui Xu, Xinglong Chen, and et al. 2024. "Predicting Coastal Water Quality with Machine Learning, A Case Study of Beibu Gulf, China" Water 16, no. 16: 2253. https://doi.org/10.3390/w16162253

Article Metrics

Article access statistics, supplementary material.

ZIP-Document (ZIP, 10144 KiB)

Further Information

Mdpi initiatives, follow mdpi.

Subscribe to receive issue release notifications and newsletters from MDPI journals