Tetrathiafulvalene-Fused Porphyrins via Quinoxaline Linkers: Symmetric and Asymmetric Donor-Acceptor Systems
Identifieur interne : 005856 ( Main/Exploration ); précédent : 005855; suivant : 005857Tetrathiafulvalene-Fused Porphyrins via Quinoxaline Linkers: Symmetric and Asymmetric Donor-Acceptor Systems
Auteurs : HONGPENG JIA [Suisse] ; Belinda Schmid [Suisse] ; Shi-Xia Liu [Suisse] ; Michael Jaggi [Suisse] ; Philippe Monbaron [Suisse] ; Sheshanath V. Bhosale [Australie] ; Shadi Rivadehi [Australie] ; Steven J. Langford [Australie] ; Lionel Sanguinet [France] ; Eric Levillain [France] ; Mohamed E. El-Khouly [Japon] ; Ysushi Morita [Japon] ; Shunichi Fukuzumi [Japon, Corée du Sud] ; Silvio Decurtins [Suisse]Source :
- ChemPhysChem : (Print) [ 1439-4235 ] ; 2012.
Descripteurs français
- Pascal (Inist)
- Transfert charge, Excitation, Effet photoinduit, Fluorescence, Etude théorique, Méthode fonctionnelle densité, Etat électronique excité, Force oscillateur, Cinétique, Domaine temps fs, Spectre absorption, Domaine temps ps, Hétérocycle azote, Macrocycle, Composé minéral, Fullerènes, Dérivé de la porphyrine, Dérivé de la pyridine, Durée vie, Agrégat atomique, Carbone, Composé organique, Effet substituant, Interaction donneur accepteur, Dérivé de la quinoxaline, Orbitale frontière, C60, 3370C, 3115E.
- Wicri :
- topic : Composé minéral, Carbone.
English descriptors
- KwdEn :
- Absorption spectra, Atomic clusters, Carbon, Charge transfer, Density functional method, Donor acceptor interaction, Electronically excited state, Excitation, Fluorescence, Frontier orbital, Fullerenes, Inorganic compounds, Kinetics, Lifetime, Macrocycle, Nitrogen heterocycle, Organic compounds, Oscillator strengths, Photoinduced effect, Porphyrin derivatives, Pyridine derivatives, Quinoxaline derivatives, Substituent effect, Theoretical study, fs range, ps range.
Abstract
A tetrathiafulvalene (TTF) donor is annulated to porphyrins (P) via quinoxaline linkers to form novel symmetric P-TTF-P triads 1 a-c and asymmetric P-TTF dyads 2a,b in good yields. These planar and extended π-conjugated molecules absorb light over a wide region of the UVNis spectrum as a result of additional charge-transfer excitations within the donor-acceptor assemblies. Quantum-chemical calculations elucidate the nature of the electronically excited states. The compounds are electrochemically amphoteric and primarily exhibit low oxidation potentials. Cyclic voltammetric and spectroelectrochemical studies allow differentiation between the TTF and porphyrin sites with respect to the multiple redox processes occurring within these molecular assemblies. Transient absorption measurements give insight into the excited-state events and deliver corresponding kinetic data. Femtosecond transient absorption spectra in benzonitrile may suggest the occurrence of fast charge separation from TTF to porphyrin in dyads 2a,b but not in triads 1 a-c. Clear evidence for a photoinduced and relatively long lived charge-separated state (385 ps lifetime) is obtained for a supramolecular coordination compound built from the ZnP-TTF dyad and a pyridine-functionalized C60 acceptor unit. This specific excited state results in a (ZnP-TTF).+ ...(C60py).- state. The binding constant of ZnII...py is evaluated by constructing a Benesi-Hildebrand plot based on fluorescence data. This plot yields a binding constant K of 7.20× 104 M-1, which is remarkably high for bonding of pyridine to ZnP.
Affiliations:
- Australie, Corée du Sud, France, Japon, Suisse
- Canton de Berne, Pays de la Loire, Région capitale de Séoul
- Angers, Berne, Séoul
- Université d'Angers, Université de Berne
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i1="04"><s1>Department of Material and Life Science Graduate School of Engineering, Osaka University</s1><s2>Suita, Osaka 565-0871</s2><s3>JPN</s3><sZ>11 aut.</sZ><sZ>13 aut.</sZ></inist:fA14><country>Japon</country><wicri:noRegion>Suita, Osaka 565-0871</wicri:noRegion></affiliation><affiliation wicri:level="1"><inist:fA14 i1="06"><s1>Department of Bioinspired Science Ewha Womans University</s1><s2>Seoul 120-750</s2><s3>KOR</s3><sZ>13 aut.</sZ></inist:fA14><country>Corée du Sud</country><placeName><settlement type="city">Séoul</settlement><region type="capital">Région capitale de Séoul</region></placeName></affiliation></author><author><name sortKey="Decurtins, Silvio" sort="Decurtins, Silvio" uniqKey="Decurtins S" first="Silvio" last="Decurtins">Silvio Decurtins</name><affiliation wicri:level="4"><inist:fA14 i1="01"><s1>Departement für Chemie und Biochemie Universität Bern, Freiestrasse 3</s1><s2>3012 Bern</s2><s3>CHE</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 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type="wicri:Area/Main/Curation">005856</idno><idno type="wicri:Area/Main/Exploration">005856</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a">Tetrathiafulvalene-Fused Porphyrins via Quinoxaline Linkers: Symmetric and Asymmetric Donor-Acceptor Systems</title><author><name sortKey="Hongpeng Jia" sort="Hongpeng Jia" uniqKey="Hongpeng Jia" last="Hongpeng Jia">HONGPENG JIA</name><affiliation wicri:level="4"><inist:fA14 i1="01"><s1>Departement für Chemie und Biochemie Universität Bern, Freiestrasse 3</s1><s2>3012 Bern</s2><s3>CHE</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>14 aut.</sZ></inist:fA14><country>Suisse</country><placeName><settlement type="city">Berne</settlement><region type="région" nuts="3">Canton de Berne</region><settlement type="city">Berne</settlement></placeName><orgName type="university">Université de Berne</orgName></affiliation></author><author><name sortKey="Schmid, Belinda" sort="Schmid, Belinda" uniqKey="Schmid B" first="Belinda" last="Schmid">Belinda Schmid</name><affiliation wicri:level="4"><inist:fA14 i1="01"><s1>Departement für Chemie und Biochemie Universität Bern, Freiestrasse 3</s1><s2>3012 Bern</s2><s3>CHE</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>14 aut.</sZ></inist:fA14><country>Suisse</country><placeName><settlement type="city">Berne</settlement><region type="région" nuts="3">Canton de Berne</region><settlement type="city">Berne</settlement></placeName><orgName type="university">Université de Berne</orgName></affiliation></author><author><name sortKey="Liu, Shi Xia" sort="Liu, Shi Xia" uniqKey="Liu S" first="Shi-Xia" last="Liu">Shi-Xia Liu</name><affiliation wicri:level="4"><inist:fA14 i1="01"><s1>Departement für Chemie und Biochemie Universität Bern, Freiestrasse 3</s1><s2>3012 Bern</s2><s3>CHE</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>14 aut.</sZ></inist:fA14><country>Suisse</country><placeName><settlement type="city">Berne</settlement><region type="région" nuts="3">Canton de Berne</region><settlement type="city">Berne</settlement></placeName><orgName type="university">Université de Berne</orgName></affiliation></author><author><name sortKey="Jaggi, Michael" sort="Jaggi, Michael" uniqKey="Jaggi M" first="Michael" last="Jaggi">Michael Jaggi</name><affiliation wicri:level="4"><inist:fA14 i1="01"><s1>Departement für Chemie und Biochemie Universität Bern, Freiestrasse 3</s1><s2>3012 Bern</s2><s3>CHE</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>14 aut.</sZ></inist:fA14><country>Suisse</country><placeName><settlement type="city">Berne</settlement><region type="région" nuts="3">Canton de Berne</region><settlement type="city">Berne</settlement></placeName><orgName type="university">Université de Berne</orgName></affiliation></author><author><name sortKey="Monbaron, Philippe" sort="Monbaron, Philippe" uniqKey="Monbaron P" first="Philippe" last="Monbaron">Philippe Monbaron</name><affiliation wicri:level="4"><inist:fA14 i1="01"><s1>Departement für Chemie und Biochemie Universität Bern, Freiestrasse 3</s1><s2>3012 Bern</s2><s3>CHE</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>14 aut.</sZ></inist:fA14><country>Suisse</country><placeName><settlement type="city">Berne</settlement><region type="région" nuts="3">Canton de Berne</region><settlement type="city">Berne</settlement></placeName><orgName type="university">Université de Berne</orgName></affiliation></author><author><name sortKey="Bhosale, Sheshanath V" sort="Bhosale, Sheshanath V" uniqKey="Bhosale S" first="Sheshanath V." last="Bhosale">Sheshanath V. Bhosale</name><affiliation wicri:level="1"><inist:fA14 i1="02"><s1>School of Chemistry, Monash University</s1><s2>Clayton, VIC-3800</s2><s3>AUS</s3><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ></inist:fA14><country>Australie</country><wicri:noRegion>Clayton, VIC-3800</wicri:noRegion></affiliation></author><author><name sortKey="Rivadehi, Shadi" sort="Rivadehi, Shadi" uniqKey="Rivadehi S" first="Shadi" last="Rivadehi">Shadi Rivadehi</name><affiliation wicri:level="1"><inist:fA14 i1="02"><s1>School of Chemistry, Monash University</s1><s2>Clayton, VIC-3800</s2><s3>AUS</s3><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ></inist:fA14><country>Australie</country><wicri:noRegion>Clayton, VIC-3800</wicri:noRegion></affiliation></author><author><name sortKey="Langford, Steven J" sort="Langford, Steven J" uniqKey="Langford S" first="Steven J." last="Langford">Steven J. Langford</name><affiliation wicri:level="1"><inist:fA14 i1="02"><s1>School of Chemistry, Monash University</s1><s2>Clayton, VIC-3800</s2><s3>AUS</s3><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ></inist:fA14><country>Australie</country><wicri:noRegion>Clayton, VIC-3800</wicri:noRegion></affiliation></author><author><name sortKey="Sanguinet, Lionel" sort="Sanguinet, Lionel" uniqKey="Sanguinet L" first="Lionel" last="Sanguinet">Lionel Sanguinet</name><affiliation wicri:level="4"><inist:fA14 i1="03"><s1>Institut des Sciences et Technologies Moleculaires d'Angers Université d'Angers, CNRS UMR 6200 2 Bd Lavoisier</s1><s2>49045 Angers</s2><s3>FRA</s3><sZ>9 aut.</sZ><sZ>10 aut.</sZ></inist:fA14><country>France</country><placeName><region type="region" nuts="2">Pays de la Loire</region><settlement type="city">Angers</settlement><settlement type="city">Angers</settlement></placeName><orgName type="university">Université d'Angers</orgName></affiliation></author><author><name sortKey="Levillain, Eric" sort="Levillain, Eric" uniqKey="Levillain E" first="Eric" last="Levillain">Eric Levillain</name><affiliation wicri:level="4"><inist:fA14 i1="03"><s1>Institut des Sciences et Technologies Moleculaires d'Angers Université d'Angers, CNRS UMR 6200 2 Bd Lavoisier</s1><s2>49045 Angers</s2><s3>FRA</s3><sZ>9 aut.</sZ><sZ>10 aut.</sZ></inist:fA14><country>France</country><placeName><region type="region" nuts="2">Pays de la Loire</region><settlement type="city">Angers</settlement><settlement type="city">Angers</settlement></placeName><orgName type="university">Université d'Angers</orgName></affiliation></author><author><name sortKey="El Khouly, Mohamed E" sort="El Khouly, Mohamed E" uniqKey="El Khouly M" first="Mohamed E." last="El-Khouly">Mohamed E. El-Khouly</name><affiliation wicri:level="1"><inist:fA14 i1="04"><s1>Department of Material and Life Science Graduate School of Engineering, Osaka University</s1><s2>Suita, Osaka 565-0871</s2><s3>JPN</s3><sZ>11 aut.</sZ><sZ>13 aut.</sZ></inist:fA14><country>Japon</country><wicri:noRegion>Suita, Osaka 565-0871</wicri:noRegion></affiliation></author><author><name sortKey="Morita, Ysushi" sort="Morita, Ysushi" uniqKey="Morita Y" first="Ysushi" last="Morita">Ysushi Morita</name><affiliation wicri:level="1"><inist:fA14 i1="05"><s1>Department of Chemistry Graduate School of Science, Osaka University 1-1 Machikaneyama</s1><s2>Toyonaka, Osaka-560-0043</s2><s3>JPN</s3><sZ>12 aut.</sZ></inist:fA14><country>Japon</country><wicri:noRegion>Toyonaka, Osaka-560-0043</wicri:noRegion></affiliation></author><author><name sortKey="Fukuzumi, Shunichi" sort="Fukuzumi, Shunichi" uniqKey="Fukuzumi S" first="Shunichi" last="Fukuzumi">Shunichi Fukuzumi</name><affiliation wicri:level="1"><inist:fA14 i1="04"><s1>Department of Material and Life Science Graduate School of Engineering, Osaka University</s1><s2>Suita, Osaka 565-0871</s2><s3>JPN</s3><sZ>11 aut.</sZ><sZ>13 aut.</sZ></inist:fA14><country>Japon</country><wicri:noRegion>Suita, Osaka 565-0871</wicri:noRegion></affiliation><affiliation wicri:level="1"><inist:fA14 i1="06"><s1>Department of Bioinspired Science Ewha Womans University</s1><s2>Seoul 120-750</s2><s3>KOR</s3><sZ>13 aut.</sZ></inist:fA14><country>Corée du Sud</country><placeName><settlement type="city">Séoul</settlement><region type="capital">Région capitale de Séoul</region></placeName></affiliation></author><author><name sortKey="Decurtins, Silvio" sort="Decurtins, Silvio" uniqKey="Decurtins S" first="Silvio" last="Decurtins">Silvio Decurtins</name><affiliation wicri:level="4"><inist:fA14 i1="01"><s1>Departement für Chemie und Biochemie Universität Bern, Freiestrasse 3</s1><s2>3012 Bern</s2><s3>CHE</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>14 aut.</sZ></inist:fA14><country>Suisse</country><placeName><settlement type="city">Berne</settlement><region type="région" nuts="3">Canton de Berne</region><settlement type="city">Berne</settlement></placeName><orgName type="university">Université de Berne</orgName></affiliation></author></analytic><series><title level="j" type="main">ChemPhysChem : (Print)</title><title level="j" type="abbreviated">ChemPhysChem : (Print)</title><idno type="ISSN">1439-4235</idno><imprint><date when="2012">2012</date></imprint></series></biblStruct></sourceDesc><seriesStmt><title level="j" type="main">ChemPhysChem : (Print)</title><title level="j" type="abbreviated">ChemPhysChem : (Print)</title><idno type="ISSN">1439-4235</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Absorption spectra</term><term>Atomic clusters</term><term>Carbon</term><term>Charge transfer</term><term>Density functional method</term><term>Donor acceptor interaction</term><term>Electronically excited state</term><term>Excitation</term><term>Fluorescence</term><term>Frontier orbital</term><term>Fullerenes</term><term>Inorganic compounds</term><term>Kinetics</term><term>Lifetime</term><term>Macrocycle</term><term>Nitrogen heterocycle</term><term>Organic compounds</term><term>Oscillator strengths</term><term>Photoinduced effect</term><term>Porphyrin derivatives</term><term>Pyridine derivatives</term><term>Quinoxaline derivatives</term><term>Substituent effect</term><term>Theoretical study</term><term>fs range</term><term>ps range</term></keywords><keywords scheme="Pascal" xml:lang="fr"><term>Transfert charge</term><term>Excitation</term><term>Effet photoinduit</term><term>Fluorescence</term><term>Etude théorique</term><term>Méthode fonctionnelle densité</term><term>Etat électronique excité</term><term>Force oscillateur</term><term>Cinétique</term><term>Domaine temps fs</term><term>Spectre absorption</term><term>Domaine temps ps</term><term>Hétérocycle azote</term><term>Macrocycle</term><term>Composé minéral</term><term>Fullerènes</term><term>Dérivé de la porphyrine</term><term>Dérivé de la pyridine</term><term>Durée vie</term><term>Agrégat atomique</term><term>Carbone</term><term>Composé organique</term><term>Effet substituant</term><term>Interaction donneur accepteur</term><term>Dérivé de la quinoxaline</term><term>Orbitale frontière</term><term>C60</term><term>3370C</term><term>3115E</term></keywords><keywords scheme="Wicri" type="topic" xml:lang="fr"><term>Composé minéral</term><term>Carbone</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">A tetrathiafulvalene (TTF) donor is annulated to porphyrins (P) via quinoxaline linkers to form novel symmetric P-TTF-P triads 1 a-c and asymmetric P-TTF dyads 2a,b in good yields. These planar and extended π-conjugated molecules absorb light over a wide region of the UVNis spectrum as a result of additional charge-transfer excitations within the donor-acceptor assemblies. Quantum-chemical calculations elucidate the nature of the electronically excited states. The compounds are electrochemically amphoteric and primarily exhibit low oxidation potentials. Cyclic voltammetric and spectroelectrochemical studies allow differentiation between the TTF and porphyrin sites with respect to the multiple redox processes occurring within these molecular assemblies. Transient absorption measurements give insight into the excited-state events and deliver corresponding kinetic data. Femtosecond transient absorption spectra in benzonitrile may suggest the occurrence of fast charge separation from TTF to porphyrin in dyads 2a,b but not in triads 1 a-c. Clear evidence for a photoinduced and relatively long lived charge-separated state (385 ps lifetime) is obtained for a supramolecular coordination compound built from the ZnP-TTF dyad and a pyridine-functionalized C<sub>60</sub> acceptor unit. This specific excited state results in a (ZnP-TTF)<sup>.+</sup> ...(C<sub>60</sub>py)<sup>.-</sup> state. The binding constant of Zn<sup>II</sup>...py is evaluated by constructing a Benesi-Hildebrand plot based on fluorescence data. This plot yields a binding constant K of 7.20× 10<sup>4</sup> M<sup>-1</sup>, which is remarkably high for bonding of pyridine to ZnP.</div></front></TEI><affiliations><list><country><li>Australie</li><li>Corée du Sud</li><li>France</li><li>Japon</li><li>Suisse</li></country><region><li>Canton de Berne</li><li>Pays de la Loire</li><li>Région capitale de Séoul</li></region><settlement><li>Angers</li><li>Berne</li><li>Séoul</li></settlement><orgName><li>Université d'Angers</li><li>Université de Berne</li></orgName></list><tree><country name="Suisse"><region name="Canton de Berne"><name sortKey="Hongpeng Jia" sort="Hongpeng Jia" uniqKey="Hongpeng Jia" last="Hongpeng Jia">HONGPENG JIA</name></region><name sortKey="Decurtins, Silvio" sort="Decurtins, Silvio" uniqKey="Decurtins S" first="Silvio" last="Decurtins">Silvio Decurtins</name><name sortKey="Jaggi, Michael" sort="Jaggi, Michael" uniqKey="Jaggi M" first="Michael" last="Jaggi">Michael Jaggi</name><name sortKey="Liu, Shi Xia" sort="Liu, Shi Xia" uniqKey="Liu S" first="Shi-Xia" last="Liu">Shi-Xia Liu</name><name sortKey="Monbaron, Philippe" sort="Monbaron, Philippe" uniqKey="Monbaron P" first="Philippe" last="Monbaron">Philippe Monbaron</name><name sortKey="Schmid, Belinda" sort="Schmid, Belinda" uniqKey="Schmid B" first="Belinda" last="Schmid">Belinda Schmid</name></country><country name="Australie"><noRegion><name sortKey="Bhosale, Sheshanath V" sort="Bhosale, Sheshanath V" uniqKey="Bhosale S" first="Sheshanath V." last="Bhosale">Sheshanath V. Bhosale</name></noRegion><name sortKey="Langford, Steven J" sort="Langford, Steven J" uniqKey="Langford S" first="Steven J." last="Langford">Steven J. Langford</name><name sortKey="Rivadehi, Shadi" sort="Rivadehi, Shadi" uniqKey="Rivadehi S" first="Shadi" last="Rivadehi">Shadi Rivadehi</name></country><country name="France"><region name="Pays de la Loire"><name sortKey="Sanguinet, Lionel" sort="Sanguinet, Lionel" uniqKey="Sanguinet L" first="Lionel" last="Sanguinet">Lionel Sanguinet</name></region><name sortKey="Levillain, Eric" sort="Levillain, Eric" uniqKey="Levillain E" first="Eric" last="Levillain">Eric Levillain</name></country><country name="Japon"><noRegion><name sortKey="El Khouly, Mohamed E" sort="El Khouly, Mohamed E" uniqKey="El Khouly M" first="Mohamed E." last="El-Khouly">Mohamed E. El-Khouly</name></noRegion><name sortKey="Fukuzumi, Shunichi" sort="Fukuzumi, Shunichi" uniqKey="Fukuzumi S" first="Shunichi" last="Fukuzumi">Shunichi Fukuzumi</name><name sortKey="Morita, Ysushi" sort="Morita, Ysushi" uniqKey="Morita Y" first="Ysushi" last="Morita">Ysushi Morita</name></country><country name="Corée du Sud"><region name="Région capitale de Séoul"><name sortKey="Fukuzumi, Shunichi" sort="Fukuzumi, Shunichi" uniqKey="Fukuzumi S" first="Shunichi" last="Fukuzumi">Shunichi Fukuzumi</name></region></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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