A Photoexcitation‐Induced Twisted Intramolecular Charge Shuttle
Charge transfer and separation are important processes governing numerous chemical reactions. Fundamental understanding of these processes and the underlying mechanisms is critical for photochemistry. Herein, we report the discovery of a new charge‐transfer and separation process, namely the twisted...
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Veröffentlicht in: | Angewandte Chemie International Edition 2019-05, Vol.58 (21), p.7073-7077 |
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creator | Chi, Weijie Qiao, Qinglong Lee, Richmond Liu, Wenjuan Teo, Yock Siong Gu, Danning Lang, Matthew John Chang, Young‐Tae Xu, Zhaochao Liu, Xiaogang |
description | Charge transfer and separation are important processes governing numerous chemical reactions. Fundamental understanding of these processes and the underlying mechanisms is critical for photochemistry. Herein, we report the discovery of a new charge‐transfer and separation process, namely the twisted intramolecular charge shuttle (TICS). In TICS systems, the donor and acceptor moieties dynamically switch roles in the excited state because of an approximately 90° intramolecular rotation. TICS systems thus exhibit charge shuttling. TICSs exist in several chemical families of fluorophores (such as coumarin, BODIPY, and oxygen/carbon/silicon–rhodamine), and could be utilized to construct functional fluorescent probes (i.e., viscosity‐ or biomolecule‐sensing probes). The discovery of the TICS process expands the current perspectives of charge‐transfer processes and will inspire future applications.
Twisted intramolecular charge shuttle (TICS): In TICS systems, the donor and acceptor moieties dynamically switch roles in the excited state due to an approximately 90° intramolecular rotation that is induced upon photoexcitation. This results in charge shuttling. TICSs exist in several families of fluorophores and could be utilized in the construction of fluorescent probes. |
doi_str_mv | 10.1002/anie.201902766 |
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Twisted intramolecular charge shuttle (TICS): In TICS systems, the donor and acceptor moieties dynamically switch roles in the excited state due to an approximately 90° intramolecular rotation that is induced upon photoexcitation. This results in charge shuttling. TICSs exist in several families of fluorophores and could be utilized in the construction of fluorescent probes.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201902766</identifier><identifier>PMID: 30916461</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Biomolecules ; biosensors ; Charge transfer ; charge transfer and separation ; Chemical compounds ; Chemical reactions ; Coumarin ; donor–acceptor systems ; Fluorescent indicators ; fluorescent probes ; fluorophore ; Fluorophores ; Organic chemistry ; Photochemistry ; Photoexcitation ; Probes ; Rhodamine ; Separation ; Viscosity</subject><ispartof>Angewandte Chemie International Edition, 2019-05, Vol.58 (21), p.7073-7077</ispartof><rights>2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4766-944959fffdd7e71f9b511e927377dee279e98c04c82a82ca4162b5fc34fa65523</citedby><cites>FETCH-LOGICAL-c4766-944959fffdd7e71f9b511e927377dee279e98c04c82a82ca4162b5fc34fa65523</cites><orcidid>0000-0002-1927-3688</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fanie.201902766$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201902766$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>315,781,785,1418,27929,27930,45579,45580</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30916461$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Chi, Weijie</creatorcontrib><creatorcontrib>Qiao, Qinglong</creatorcontrib><creatorcontrib>Lee, Richmond</creatorcontrib><creatorcontrib>Liu, Wenjuan</creatorcontrib><creatorcontrib>Teo, Yock Siong</creatorcontrib><creatorcontrib>Gu, Danning</creatorcontrib><creatorcontrib>Lang, Matthew John</creatorcontrib><creatorcontrib>Chang, Young‐Tae</creatorcontrib><creatorcontrib>Xu, Zhaochao</creatorcontrib><creatorcontrib>Liu, Xiaogang</creatorcontrib><title>A Photoexcitation‐Induced Twisted Intramolecular Charge Shuttle</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>Charge transfer and separation are important processes governing numerous chemical reactions. Fundamental understanding of these processes and the underlying mechanisms is critical for photochemistry. Herein, we report the discovery of a new charge‐transfer and separation process, namely the twisted intramolecular charge shuttle (TICS). In TICS systems, the donor and acceptor moieties dynamically switch roles in the excited state because of an approximately 90° intramolecular rotation. TICS systems thus exhibit charge shuttling. TICSs exist in several chemical families of fluorophores (such as coumarin, BODIPY, and oxygen/carbon/silicon–rhodamine), and could be utilized to construct functional fluorescent probes (i.e., viscosity‐ or biomolecule‐sensing probes). The discovery of the TICS process expands the current perspectives of charge‐transfer processes and will inspire future applications.
Twisted intramolecular charge shuttle (TICS): In TICS systems, the donor and acceptor moieties dynamically switch roles in the excited state due to an approximately 90° intramolecular rotation that is induced upon photoexcitation. This results in charge shuttling. TICSs exist in several families of fluorophores and could be utilized in the construction of fluorescent probes.</description><subject>Biomolecules</subject><subject>biosensors</subject><subject>Charge transfer</subject><subject>charge transfer and separation</subject><subject>Chemical compounds</subject><subject>Chemical reactions</subject><subject>Coumarin</subject><subject>donor–acceptor systems</subject><subject>Fluorescent indicators</subject><subject>fluorescent probes</subject><subject>fluorophore</subject><subject>Fluorophores</subject><subject>Organic chemistry</subject><subject>Photochemistry</subject><subject>Photoexcitation</subject><subject>Probes</subject><subject>Rhodamine</subject><subject>Separation</subject><subject>Viscosity</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNqFkL1OwzAUhS0EoqWwMqJILCwpthPb8VhVBSJVgESZLde5oanyU-xEpRuPwDPyJLhqAYmF6dzhu0fnHITOCR4SjOm1rgsYUkwkpoLzA9QnjJIwEiI69HccRaFIGOmhE-eWnk8SzI9RL8KS8JiTPhqNgsdF0zbwZopWt0VTf75_pHXWGciC2bpwrde0bq2umhJMV2objBfavkDwtOjatoRTdJTr0sHZXgfo-WYyG9-F04fbdDyahib2yUIZx5LJPM-zTIAguZwzQkBS4bNmAFRIkInBsUmoTqjRMeF0znITxbnmjNFogK52vivbvHbgWlUVzkBZ6hqazilKZMKY74U9evkHXTadrX06RSmNhG_OuaeGO8rYxjkLuVrZotJ2owhW23HVdlz1M65_uNjbdvMKsh_8e00PyB2wLkrY_GOnRvfp5Nf8C8huhcs</recordid><startdate>20190520</startdate><enddate>20190520</enddate><creator>Chi, Weijie</creator><creator>Qiao, Qinglong</creator><creator>Lee, Richmond</creator><creator>Liu, Wenjuan</creator><creator>Teo, Yock Siong</creator><creator>Gu, Danning</creator><creator>Lang, Matthew John</creator><creator>Chang, Young‐Tae</creator><creator>Xu, Zhaochao</creator><creator>Liu, Xiaogang</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-1927-3688</orcidid></search><sort><creationdate>20190520</creationdate><title>A Photoexcitation‐Induced Twisted Intramolecular Charge Shuttle</title><author>Chi, Weijie ; Qiao, Qinglong ; Lee, Richmond ; Liu, Wenjuan ; Teo, Yock Siong ; Gu, Danning ; Lang, Matthew John ; Chang, Young‐Tae ; Xu, Zhaochao ; Liu, Xiaogang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4766-944959fffdd7e71f9b511e927377dee279e98c04c82a82ca4162b5fc34fa65523</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Biomolecules</topic><topic>biosensors</topic><topic>Charge transfer</topic><topic>charge transfer and separation</topic><topic>Chemical compounds</topic><topic>Chemical reactions</topic><topic>Coumarin</topic><topic>donor–acceptor systems</topic><topic>Fluorescent indicators</topic><topic>fluorescent probes</topic><topic>fluorophore</topic><topic>Fluorophores</topic><topic>Organic chemistry</topic><topic>Photochemistry</topic><topic>Photoexcitation</topic><topic>Probes</topic><topic>Rhodamine</topic><topic>Separation</topic><topic>Viscosity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chi, Weijie</creatorcontrib><creatorcontrib>Qiao, Qinglong</creatorcontrib><creatorcontrib>Lee, Richmond</creatorcontrib><creatorcontrib>Liu, Wenjuan</creatorcontrib><creatorcontrib>Teo, Yock Siong</creatorcontrib><creatorcontrib>Gu, Danning</creatorcontrib><creatorcontrib>Lang, Matthew John</creatorcontrib><creatorcontrib>Chang, Young‐Tae</creatorcontrib><creatorcontrib>Xu, Zhaochao</creatorcontrib><creatorcontrib>Liu, Xiaogang</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Chi, Weijie</au><au>Qiao, Qinglong</au><au>Lee, Richmond</au><au>Liu, Wenjuan</au><au>Teo, Yock Siong</au><au>Gu, Danning</au><au>Lang, Matthew John</au><au>Chang, Young‐Tae</au><au>Xu, Zhaochao</au><au>Liu, Xiaogang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Photoexcitation‐Induced Twisted Intramolecular Charge Shuttle</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2019-05-20</date><risdate>2019</risdate><volume>58</volume><issue>21</issue><spage>7073</spage><epage>7077</epage><pages>7073-7077</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>Charge transfer and separation are important processes governing numerous chemical reactions. Fundamental understanding of these processes and the underlying mechanisms is critical for photochemistry. Herein, we report the discovery of a new charge‐transfer and separation process, namely the twisted intramolecular charge shuttle (TICS). In TICS systems, the donor and acceptor moieties dynamically switch roles in the excited state because of an approximately 90° intramolecular rotation. TICS systems thus exhibit charge shuttling. TICSs exist in several chemical families of fluorophores (such as coumarin, BODIPY, and oxygen/carbon/silicon–rhodamine), and could be utilized to construct functional fluorescent probes (i.e., viscosity‐ or biomolecule‐sensing probes). The discovery of the TICS process expands the current perspectives of charge‐transfer processes and will inspire future applications.
Twisted intramolecular charge shuttle (TICS): In TICS systems, the donor and acceptor moieties dynamically switch roles in the excited state due to an approximately 90° intramolecular rotation that is induced upon photoexcitation. This results in charge shuttling. TICSs exist in several families of fluorophores and could be utilized in the construction of fluorescent probes.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>30916461</pmid><doi>10.1002/anie.201902766</doi><tpages>5</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0002-1927-3688</orcidid></addata></record> |
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subjects | Biomolecules biosensors Charge transfer charge transfer and separation Chemical compounds Chemical reactions Coumarin donor–acceptor systems Fluorescent indicators fluorescent probes fluorophore Fluorophores Organic chemistry Photochemistry Photoexcitation Probes Rhodamine Separation Viscosity |
title | A Photoexcitation‐Induced Twisted Intramolecular Charge Shuttle |
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