Sensing mechanism for a fluoride chemosensor: invalidity of excited-state proton transfer mechanism
Our density functional theory (DFT)/time-dependent DFT calculations for the fluoride anion sensor, 5,7-dibromo-8-tert-butyldimethylsilyloxy-2-methylquinoline (DBM), suggested a different sensing mechanism from the experimentally proposed one (Chem. Commun., 2011, 47, 7098). Instead of the formation...
Gespeichert in:
| Veröffentlicht in: | Physical chemistry chemical physics : PCCP 2013-10, Vol.15 (38), p.16183-16189 |
|---|---|
| Hauptverfasser: | , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 16189 |
|---|---|
| container_issue | 38 |
| container_start_page | 16183 |
| container_title | Physical chemistry chemical physics : PCCP |
| container_volume | 15 |
| creator | CHEN, Jun-Sheng ZHOU, Pan-Wang YANG, Song-Qiu FU, Ai-Ping CHU, Tian-Shu |
| description | Our density functional theory (DFT)/time-dependent DFT calculations for the fluoride anion sensor, 5,7-dibromo-8-tert-butyldimethylsilyloxy-2-methylquinoline (DBM), suggested a different sensing mechanism from the experimentally proposed one (Chem. Commun., 2011, 47, 7098). Instead of the formation of fluoride-hydrogen-bond complex (DBMOHF) and excited-state proton transfer mechanism, the theoretical results predicted a sensing mechanism based on desilylation reaction and intramolecular charge transfer (ICT). The fluoride anion reacted with DBM and formed an anion (DBMO), with the ICT causing a red shift in the absorbance and emission spectra of the latter. The calculated vertical excitation energies in the ground and first excited states of both DBM and DBMO, as well as the calculated (1)H NMR spectra, significantly reproduced the experimental measurements, providing additional proofs for our proposed sensing mechanism for DBM. |
| doi_str_mv | 10.1039/c3cp51482j |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1567074898</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1432617008</sourcerecordid><originalsourceid>FETCH-LOGICAL-c523t-2f51d93e7591b6d80bedac5a72de99e984a248e7668350e9ca361c2644cc65783</originalsourceid><addsrcrecordid>eNqN0EtLAzEUhuEgiq3VjT9AshFEGM394k7EGwgu1PWQZs7YlJlJTaZi_71TrHbrKlk8fBxehI4puaCE20vP_UJSYdh8B42pULywxIjdv79WI3SQ85wQQiXl-2jEuLWKWDZG_gW6HLp33IKfuS7kFtcxYYfrZhlTqAD7GbQxDyqmKxy6T9eEKvQrHGsMXz70UBW5dz3gRYp97HCfXJdrSNvFQ7RXuybD0eadoLe729ebh-Lp-f7x5vqp8JLxvmC1pJXloKWlU1UZMoXKeek0q8BasEY4JgxopQyXBKx3XFHPlBDeK6kNn6Czn93hko8l5L5sQ_bQNK6DuMwllUoTLYz9BxWcKaoJWdPzH-pTzDlBXS5SaF1alZSU6_7ltv-ATza7y2kL1R_9DT6A0w1w2bumHmL5kLdOa6mEofwbsnuOSg</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1432617008</pqid></control><display><type>article</type><title>Sensing mechanism for a fluoride chemosensor: invalidity of excited-state proton transfer mechanism</title><source>Royal Society Of Chemistry Journals 2008-</source><source>Alma/SFX Local Collection</source><creator>CHEN, Jun-Sheng ; ZHOU, Pan-Wang ; YANG, Song-Qiu ; FU, Ai-Ping ; CHU, Tian-Shu</creator><creatorcontrib>CHEN, Jun-Sheng ; ZHOU, Pan-Wang ; YANG, Song-Qiu ; FU, Ai-Ping ; CHU, Tian-Shu</creatorcontrib><description>Our density functional theory (DFT)/time-dependent DFT calculations for the fluoride anion sensor, 5,7-dibromo-8-tert-butyldimethylsilyloxy-2-methylquinoline (DBM), suggested a different sensing mechanism from the experimentally proposed one (Chem. Commun., 2011, 47, 7098). Instead of the formation of fluoride-hydrogen-bond complex (DBMOHF) and excited-state proton transfer mechanism, the theoretical results predicted a sensing mechanism based on desilylation reaction and intramolecular charge transfer (ICT). The fluoride anion reacted with DBM and formed an anion (DBMO), with the ICT causing a red shift in the absorbance and emission spectra of the latter. The calculated vertical excitation energies in the ground and first excited states of both DBM and DBMO, as well as the calculated (1)H NMR spectra, significantly reproduced the experimental measurements, providing additional proofs for our proposed sensing mechanism for DBM.</description><identifier>ISSN: 1463-9076</identifier><identifier>EISSN: 1463-9084</identifier><identifier>DOI: 10.1039/c3cp51482j</identifier><identifier>PMID: 23996092</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Anions ; Charge transfer ; Chemistry ; Detection ; Doppler effect ; Exact sciences and technology ; Excitation ; Excitation spectra ; Fluorides ; General and physical chemistry ; Mathematical analysis</subject><ispartof>Physical chemistry chemical physics : PCCP, 2013-10, Vol.15 (38), p.16183-16189</ispartof><rights>2014 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c523t-2f51d93e7591b6d80bedac5a72de99e984a248e7668350e9ca361c2644cc65783</citedby><cites>FETCH-LOGICAL-c523t-2f51d93e7591b6d80bedac5a72de99e984a248e7668350e9ca361c2644cc65783</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=27756481$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23996092$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>CHEN, Jun-Sheng</creatorcontrib><creatorcontrib>ZHOU, Pan-Wang</creatorcontrib><creatorcontrib>YANG, Song-Qiu</creatorcontrib><creatorcontrib>FU, Ai-Ping</creatorcontrib><creatorcontrib>CHU, Tian-Shu</creatorcontrib><title>Sensing mechanism for a fluoride chemosensor: invalidity of excited-state proton transfer mechanism</title><title>Physical chemistry chemical physics : PCCP</title><addtitle>Phys Chem Chem Phys</addtitle><description>Our density functional theory (DFT)/time-dependent DFT calculations for the fluoride anion sensor, 5,7-dibromo-8-tert-butyldimethylsilyloxy-2-methylquinoline (DBM), suggested a different sensing mechanism from the experimentally proposed one (Chem. Commun., 2011, 47, 7098). Instead of the formation of fluoride-hydrogen-bond complex (DBMOHF) and excited-state proton transfer mechanism, the theoretical results predicted a sensing mechanism based on desilylation reaction and intramolecular charge transfer (ICT). The fluoride anion reacted with DBM and formed an anion (DBMO), with the ICT causing a red shift in the absorbance and emission spectra of the latter. The calculated vertical excitation energies in the ground and first excited states of both DBM and DBMO, as well as the calculated (1)H NMR spectra, significantly reproduced the experimental measurements, providing additional proofs for our proposed sensing mechanism for DBM.</description><subject>Anions</subject><subject>Charge transfer</subject><subject>Chemistry</subject><subject>Detection</subject><subject>Doppler effect</subject><subject>Exact sciences and technology</subject><subject>Excitation</subject><subject>Excitation spectra</subject><subject>Fluorides</subject><subject>General and physical chemistry</subject><subject>Mathematical analysis</subject><issn>1463-9076</issn><issn>1463-9084</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNqN0EtLAzEUhuEgiq3VjT9AshFEGM394k7EGwgu1PWQZs7YlJlJTaZi_71TrHbrKlk8fBxehI4puaCE20vP_UJSYdh8B42pULywxIjdv79WI3SQ85wQQiXl-2jEuLWKWDZG_gW6HLp33IKfuS7kFtcxYYfrZhlTqAD7GbQxDyqmKxy6T9eEKvQrHGsMXz70UBW5dz3gRYp97HCfXJdrSNvFQ7RXuybD0eadoLe729ebh-Lp-f7x5vqp8JLxvmC1pJXloKWlU1UZMoXKeek0q8BasEY4JgxopQyXBKx3XFHPlBDeK6kNn6Czn93hko8l5L5sQ_bQNK6DuMwllUoTLYz9BxWcKaoJWdPzH-pTzDlBXS5SaF1alZSU6_7ltv-ATza7y2kL1R_9DT6A0w1w2bumHmL5kLdOa6mEofwbsnuOSg</recordid><startdate>20131014</startdate><enddate>20131014</enddate><creator>CHEN, Jun-Sheng</creator><creator>ZHOU, Pan-Wang</creator><creator>YANG, Song-Qiu</creator><creator>FU, Ai-Ping</creator><creator>CHU, Tian-Shu</creator><general>Royal Society of Chemistry</general><scope>IQODW</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20131014</creationdate><title>Sensing mechanism for a fluoride chemosensor: invalidity of excited-state proton transfer mechanism</title><author>CHEN, Jun-Sheng ; ZHOU, Pan-Wang ; YANG, Song-Qiu ; FU, Ai-Ping ; CHU, Tian-Shu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c523t-2f51d93e7591b6d80bedac5a72de99e984a248e7668350e9ca361c2644cc65783</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Anions</topic><topic>Charge transfer</topic><topic>Chemistry</topic><topic>Detection</topic><topic>Doppler effect</topic><topic>Exact sciences and technology</topic><topic>Excitation</topic><topic>Excitation spectra</topic><topic>Fluorides</topic><topic>General and physical chemistry</topic><topic>Mathematical analysis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>CHEN, Jun-Sheng</creatorcontrib><creatorcontrib>ZHOU, Pan-Wang</creatorcontrib><creatorcontrib>YANG, Song-Qiu</creatorcontrib><creatorcontrib>FU, Ai-Ping</creatorcontrib><creatorcontrib>CHU, Tian-Shu</creatorcontrib><collection>Pascal-Francis</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Physical chemistry chemical physics : PCCP</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>CHEN, Jun-Sheng</au><au>ZHOU, Pan-Wang</au><au>YANG, Song-Qiu</au><au>FU, Ai-Ping</au><au>CHU, Tian-Shu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Sensing mechanism for a fluoride chemosensor: invalidity of excited-state proton transfer mechanism</atitle><jtitle>Physical chemistry chemical physics : PCCP</jtitle><addtitle>Phys Chem Chem Phys</addtitle><date>2013-10-14</date><risdate>2013</risdate><volume>15</volume><issue>38</issue><spage>16183</spage><epage>16189</epage><pages>16183-16189</pages><issn>1463-9076</issn><eissn>1463-9084</eissn><abstract>Our density functional theory (DFT)/time-dependent DFT calculations for the fluoride anion sensor, 5,7-dibromo-8-tert-butyldimethylsilyloxy-2-methylquinoline (DBM), suggested a different sensing mechanism from the experimentally proposed one (Chem. Commun., 2011, 47, 7098). Instead of the formation of fluoride-hydrogen-bond complex (DBMOHF) and excited-state proton transfer mechanism, the theoretical results predicted a sensing mechanism based on desilylation reaction and intramolecular charge transfer (ICT). The fluoride anion reacted with DBM and formed an anion (DBMO), with the ICT causing a red shift in the absorbance and emission spectra of the latter. The calculated vertical excitation energies in the ground and first excited states of both DBM and DBMO, as well as the calculated (1)H NMR spectra, significantly reproduced the experimental measurements, providing additional proofs for our proposed sensing mechanism for DBM.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><pmid>23996092</pmid><doi>10.1039/c3cp51482j</doi><tpages>7</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1463-9076 |
| ispartof | Physical chemistry chemical physics : PCCP, 2013-10, Vol.15 (38), p.16183-16189 |
| issn | 1463-9076 1463-9084 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1567074898 |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Anions Charge transfer Chemistry Detection Doppler effect Exact sciences and technology Excitation Excitation spectra Fluorides General and physical chemistry Mathematical analysis |
| title | Sensing mechanism for a fluoride chemosensor: invalidity of excited-state proton transfer mechanism |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-21T06%3A15%3A25IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Sensing%20mechanism%20for%20a%20fluoride%20chemosensor:%20invalidity%20of%20excited-state%20proton%20transfer%20mechanism&rft.jtitle=Physical%20chemistry%20chemical%20physics%20:%20PCCP&rft.au=CHEN,%20Jun-Sheng&rft.date=2013-10-14&rft.volume=15&rft.issue=38&rft.spage=16183&rft.epage=16189&rft.pages=16183-16189&rft.issn=1463-9076&rft.eissn=1463-9084&rft_id=info:doi/10.1039/c3cp51482j&rft_dat=%3Cproquest_cross%3E1432617008%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1432617008&rft_id=info:pmid/23996092&rfr_iscdi=true |