The Role of Linkers in the Excited-State Dynamic Planarization Processes of Macrocyclic Oligothiophene 12-Mers.
Identifieur interne : 001318 ( PubMed/Checkpoint ); précédent : 001317; suivant : 001319The Role of Linkers in the Excited-State Dynamic Planarization Processes of Macrocyclic Oligothiophene 12-Mers.
Auteurs : Woojae Kim [Corée du Sud] ; Jooyoung Sung [Corée du Sud] ; Kyu Hyung Park [Corée du Sud] ; Hideyuki Shimizu [Japon] ; Mika Imamura [Japon] ; Minwoo Han [Corée du Sud] ; Eunji Sim [Corée du Sud] ; Masahiko Iyoda [Japon] ; Dongho Kim [Corée du Sud]Source :
- The journal of physical chemistry letters [ 1948-7185 ] ; 2015.
Abstract
Linkers adjoining chromophores play an important role in modulating the structure of conjugated systems, which is bound up with their photophysical properties. However, to date, the focus of works dealing with linker effects was limited only to linear π-conjugated materials, and there have been no detailed studies on cyclic counterparts. Herein we report the linker effects on the dynamic planarization processes of π-conjugated macrocyclic oligothiophene 12-mers, where the different ratio between ethynylene and vinylene linkers was chosen to control the backbone rigidity. By analyzing transient fluorescence spectra, we demonstrate that the connecting linkers play a crucial role in the excited-state dynamics of cyclic conjugated systems. Faster dynamic planarization, longer exciton delocalization length, and higher degree of planarity were observed in vinylene inserted cyclic oligothiophenes. Molecular dynamics simulations and density functional theory calculations also stress the importance of the role of linkers in modulating the structure of cyclic oligothiophenes.
DOI: 10.1021/acs.jpclett.5b02189
PubMed: 26495968
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Woojae" sort="Kim, Woojae" uniqKey="Kim W" first="Woojae" last="Kim">Woojae Kim</name><affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry and Spectroscopy Laboratory for Functional π-Electronic Systems, Yonsei University , Seoul 03722, Korea.</nlm:affiliation><country xml:lang="fr">Corée du Sud</country><wicri:regionArea>Department of Chemistry and Spectroscopy Laboratory for Functional π-Electronic Systems, Yonsei University , Seoul 03722</wicri:regionArea><placeName><settlement type="city">Séoul</settlement><region type="capital">Région capitale de Séoul</region></placeName></affiliation></author><author><name sortKey="Sung, Jooyoung" sort="Sung, Jooyoung" uniqKey="Sung J" first="Jooyoung" last="Sung">Jooyoung Sung</name><affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry and Spectroscopy Laboratory for Functional π-Electronic Systems, Yonsei University , Seoul 03722, Korea.</nlm:affiliation><country xml:lang="fr">Corée du Sud</country><wicri:regionArea>Department of Chemistry and Spectroscopy Laboratory for Functional π-Electronic Systems, Yonsei University , Seoul 03722</wicri:regionArea><placeName><settlement type="city">Séoul</settlement><region type="capital">Région capitale de Séoul</region></placeName></affiliation></author><author><name sortKey="Park, Kyu Hyung" sort="Park, Kyu Hyung" uniqKey="Park K" first="Kyu Hyung" last="Park">Kyu Hyung Park</name><affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry and Spectroscopy Laboratory for Functional π-Electronic Systems, Yonsei University , Seoul 03722, Korea.</nlm:affiliation><country xml:lang="fr">Corée du Sud</country><wicri:regionArea>Department of Chemistry and Spectroscopy Laboratory for Functional π-Electronic Systems, Yonsei University , Seoul 03722</wicri:regionArea><placeName><settlement type="city">Séoul</settlement><region type="capital">Région capitale de Séoul</region></placeName></affiliation></author><author><name sortKey="Shimizu, Hideyuki" sort="Shimizu, Hideyuki" uniqKey="Shimizu H" first="Hideyuki" last="Shimizu">Hideyuki Shimizu</name><affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University , Hachioji, Tokyo 192-0397, Japan.</nlm:affiliation><country xml:lang="fr">Japon</country><wicri:regionArea>Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University , Hachioji, Tokyo 192-0397</wicri:regionArea><placeName><settlement type="city">Tokyo</settlement><region type="région">Région de Kantō</region></placeName></affiliation></author><author><name sortKey="Imamura, Mika" sort="Imamura, Mika" uniqKey="Imamura M" first="Mika" last="Imamura">Mika Imamura</name><affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University , Hachioji, Tokyo 192-0397, Japan.</nlm:affiliation><country xml:lang="fr">Japon</country><wicri:regionArea>Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University , Hachioji, Tokyo 192-0397</wicri:regionArea><placeName><settlement type="city">Tokyo</settlement><region type="région">Région de Kantō</region></placeName></affiliation></author><author><name sortKey="Han, Minwoo" sort="Han, Minwoo" uniqKey="Han M" first="Minwoo" last="Han">Minwoo Han</name><affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry and Institute of Nano-Bio Molecular Assemblies, Yonsei University , Seoul 03722, Korea.</nlm:affiliation><country xml:lang="fr">Corée du Sud</country><wicri:regionArea>Department of Chemistry and Institute of Nano-Bio Molecular Assemblies, Yonsei University , Seoul 03722</wicri:regionArea><placeName><settlement type="city">Séoul</settlement><region type="capital">Région capitale de Séoul</region></placeName></affiliation></author><author><name sortKey="Sim, Eunji" sort="Sim, Eunji" uniqKey="Sim E" first="Eunji" last="Sim">Eunji Sim</name><affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry and Institute of Nano-Bio Molecular Assemblies, Yonsei University , Seoul 03722, Korea.</nlm:affiliation><country xml:lang="fr">Corée du Sud</country><wicri:regionArea>Department of Chemistry and Institute of Nano-Bio Molecular Assemblies, Yonsei University , Seoul 03722</wicri:regionArea><placeName><settlement type="city">Séoul</settlement><region type="capital">Région capitale de Séoul</region></placeName></affiliation></author><author><name sortKey="Iyoda, Masahiko" sort="Iyoda, Masahiko" uniqKey="Iyoda M" first="Masahiko" last="Iyoda">Masahiko Iyoda</name><affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University , Hachioji, Tokyo 192-0397, Japan.</nlm:affiliation><country xml:lang="fr">Japon</country><wicri:regionArea>Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University , Hachioji, Tokyo 192-0397</wicri:regionArea><placeName><settlement type="city">Tokyo</settlement><region type="région">Région de Kantō</region></placeName></affiliation></author><author><name sortKey="Kim, Dongho" sort="Kim, Dongho" uniqKey="Kim D" first="Dongho" last="Kim">Dongho Kim</name><affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry and Spectroscopy Laboratory for Functional π-Electronic Systems, Yonsei University , Seoul 03722, Korea.</nlm:affiliation><country xml:lang="fr">Corée du Sud</country><wicri:regionArea>Department of Chemistry and Spectroscopy Laboratory for Functional π-Electronic Systems, Yonsei University , Seoul 03722</wicri:regionArea><placeName><settlement type="city">Séoul</settlement><region type="capital">Région capitale de Séoul</region></placeName></affiliation></author></analytic><series><title level="j">The journal of physical chemistry letters</title><idno type="eISSN">1948-7185</idno><imprint><date when="2015" type="published">2015</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Linkers adjoining chromophores play an important role in modulating the structure of conjugated systems, which is bound up with their photophysical properties. However, to date, the focus of works dealing with linker effects was limited only to linear π-conjugated materials, and there have been no detailed studies on cyclic counterparts. Herein we report the linker effects on the dynamic planarization processes of π-conjugated macrocyclic oligothiophene 12-mers, where the different ratio between ethynylene and vinylene linkers was chosen to control the backbone rigidity. By analyzing transient fluorescence spectra, we demonstrate that the connecting linkers play a crucial role in the excited-state dynamics of cyclic conjugated systems. Faster dynamic planarization, longer exciton delocalization length, and higher degree of planarity were observed in vinylene inserted cyclic oligothiophenes. Molecular dynamics simulations and density functional theory calculations also stress the importance of the role of linkers in modulating the structure of cyclic oligothiophenes. </div></front></TEI><pubmed><MedlineCitation Status="PubMed-not-MEDLINE" Owner="NLM"><PMID Version="1">26495968</PMID><DateCompleted><Year>2016</Year><Month>04</Month><Day>08</Day></DateCompleted><DateRevised><Year>2016</Year><Month>01</Month><Day>02</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1948-7185</ISSN><JournalIssue CitedMedium="Internet"><Volume>6</Volume><Issue>21</Issue><PubDate><Year>2015</Year><Month>Nov</Month><Day>05</Day></PubDate></JournalIssue><Title>The journal of physical chemistry letters</Title><ISOAbbreviation>J Phys Chem Lett</ISOAbbreviation></Journal><ArticleTitle>The Role of Linkers in the Excited-State Dynamic Planarization Processes of Macrocyclic Oligothiophene 12-Mers.</ArticleTitle><Pagination><MedlinePgn>4444-50</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1021/acs.jpclett.5b02189</ELocationID><Abstract><AbstractText>Linkers adjoining chromophores play an important role in modulating the structure of conjugated systems, which is bound up with their photophysical properties. However, to date, the focus of works dealing with linker effects was limited only to linear π-conjugated materials, and there have been no detailed studies on cyclic counterparts. Herein we report the linker effects on the dynamic planarization processes of π-conjugated macrocyclic oligothiophene 12-mers, where the different ratio between ethynylene and vinylene linkers was chosen to control the backbone rigidity. By analyzing transient fluorescence spectra, we demonstrate that the connecting linkers play a crucial role in the excited-state dynamics of cyclic conjugated systems. Faster dynamic planarization, longer exciton delocalization length, and higher degree of planarity were observed in vinylene inserted cyclic oligothiophenes. Molecular dynamics simulations and density functional theory calculations also stress the importance of the role of linkers in modulating the structure of cyclic oligothiophenes. </AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Kim</LastName><ForeName>Woojae</ForeName><Initials>W</Initials><AffiliationInfo><Affiliation>Department of Chemistry and Spectroscopy Laboratory for Functional π-Electronic Systems, Yonsei University , Seoul 03722, Korea.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Sung</LastName><ForeName>Jooyoung</ForeName><Initials>J</Initials><AffiliationInfo><Affiliation>Department of Chemistry and Spectroscopy Laboratory for Functional π-Electronic Systems, Yonsei University , Seoul 03722, Korea.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Park</LastName><ForeName>Kyu Hyung</ForeName><Initials>KH</Initials><AffiliationInfo><Affiliation>Department of Chemistry and Spectroscopy Laboratory for Functional π-Electronic Systems, Yonsei University , Seoul 03722, Korea.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Shimizu</LastName><ForeName>Hideyuki</ForeName><Initials>H</Initials><AffiliationInfo><Affiliation>Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University , Hachioji, Tokyo 192-0397, Japan.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Imamura</LastName><ForeName>Mika</ForeName><Initials>M</Initials><AffiliationInfo><Affiliation>Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University , Hachioji, Tokyo 192-0397, Japan.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Han</LastName><ForeName>Minwoo</ForeName><Initials>M</Initials><AffiliationInfo><Affiliation>Department of Chemistry and Institute of Nano-Bio Molecular Assemblies, Yonsei University , Seoul 03722, Korea.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Sim</LastName><ForeName>Eunji</ForeName><Initials>E</Initials><AffiliationInfo><Affiliation>Department of Chemistry and Institute of Nano-Bio Molecular Assemblies, Yonsei University , Seoul 03722, Korea.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Iyoda</LastName><ForeName>Masahiko</ForeName><Initials>M</Initials><AffiliationInfo><Affiliation>Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University , Hachioji, Tokyo 192-0397, Japan.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Kim</LastName><ForeName>Dongho</ForeName><Initials>D</Initials><AffiliationInfo><Affiliation>Department of Chemistry and Spectroscopy Laboratory for Functional π-Electronic Systems, Yonsei University , Seoul 03722, Korea.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2015</Year><Month>10</Month><Day>28</Day></ArticleDate></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>J Phys Chem Lett</MedlineTA><NlmUniqueID>101526034</NlmUniqueID><ISSNLinking>1948-7185</ISSNLinking></MedlineJournalInfo><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">broadband fluorescence up-conversion spectroscopy</Keyword><Keyword MajorTopicYN="N">cyclic oligothiophene</Keyword><Keyword MajorTopicYN="N">dynamic planarization</Keyword><Keyword MajorTopicYN="N">linkage pattern</Keyword><Keyword MajorTopicYN="N">molecular dynamics simulations</Keyword><Keyword MajorTopicYN="N">vibronic band ratio</Keyword></KeywordList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="entrez"><Year>2015</Year><Month>10</Month><Day>27</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate 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sort="Kim, Dongho" uniqKey="Kim D" first="Dongho" last="Kim">Dongho Kim</name><name sortKey="Park, Kyu Hyung" sort="Park, Kyu Hyung" uniqKey="Park K" first="Kyu Hyung" last="Park">Kyu Hyung Park</name><name sortKey="Sim, Eunji" sort="Sim, Eunji" uniqKey="Sim E" first="Eunji" last="Sim">Eunji Sim</name><name sortKey="Sung, Jooyoung" sort="Sung, Jooyoung" uniqKey="Sung J" first="Jooyoung" last="Sung">Jooyoung Sung</name></country><country name="Japon"><region name="Région de Kantō"><name sortKey="Shimizu, Hideyuki" sort="Shimizu, Hideyuki" uniqKey="Shimizu H" first="Hideyuki" last="Shimizu">Hideyuki Shimizu</name></region><name sortKey="Imamura, Mika" sort="Imamura, Mika" uniqKey="Imamura M" first="Mika" last="Imamura">Mika Imamura</name><name sortKey="Iyoda, Masahiko" sort="Iyoda, Masahiko" uniqKey="Iyoda M" first="Masahiko" last="Iyoda">Masahiko Iyoda</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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