Tetrathiafulvalene‐Fused Porphyrins via Quinoxaline Linkers: Symmetric and Asymmetric Donor–Acceptor Systems
Identifieur interne : 005591 ( Main/Exploration ); précédent : 005590; suivant : 005592Tetrathiafulvalene‐Fused Porphyrins via Quinoxaline Linkers: Symmetric and Asymmetric Donor–Acceptor Systems
Auteurs : Hongpeng Jia [Suisse] ; Belinda Schmid [Suisse] ; Shi-Xia Liu [Suisse, Japon] ; Michael Jaggi [Suisse] ; Philippe Monbaron [Suisse] ; Sheshanath V. Bhosale [Australie, Japon] ; 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 [ 1439-4235 ] ; 2012-10-08.
English descriptors
- KwdEn :
- Absorption band, Absorption spectra, Acceptor, Asymmetric dyads, Benzonitrile, Bhosale, Calcd, Cation, Charge separation, Chem, Chemphyschem, Crossley, Crude product, Cyclic, Cyclic voltammetry, Cyclic voltammograms, Decay profile, Decurtins, Differential absorption spectra, Dominant contributions, Dyad, Electrochemical, Electron transfer, Elemental analysis calcd, Excitation, Femtosecond, Femtosecond flash photolysis, First oxidation, First oxidation process, Ftir, Fukuzumi, Gmbh, Good agreement, Homo, Information figure, Information figures, Kgaa, Levillain, Lumo, Molecular structure, Oscillator, Oscillator strengths, Oxidation potentials, Petroleum ether, Phys, Porphyrin, Porphyrin core, Porphyrin rings, Quinoxaline, Quinoxaline linkers, Radical cation, Radical cation species, Redox, Redox processes, Reference compound, Reference compounds, Room temperature, Scan rate, Singlet, Singlet porphyrin, State excitation energy oscillator strength, Subsequent reprecipitation, Supramolecular, Supramolecular triad, Time intervals, Transient spectra, Triad, Verlag, Verlag gmbh, Visible region, Voltammetry, Voltammograms, Weinheim, Weinheim chemphyschem.
- Teeft :
- Absorption band, Absorption spectra, Acceptor, Asymmetric dyads, Benzonitrile, Bhosale, Calcd, Cation, Charge separation, Chem, Chemphyschem, Crossley, Crude product, Cyclic, Cyclic voltammetry, Cyclic voltammograms, Decay profile, Decurtins, Differential absorption spectra, Dominant contributions, Dyad, Electrochemical, Electron transfer, Elemental analysis calcd, Excitation, Femtosecond, Femtosecond flash photolysis, First oxidation, First oxidation process, Ftir, Fukuzumi, Gmbh, Good agreement, Homo, Information figure, Information figures, Kgaa, Levillain, Lumo, Molecular structure, Oscillator, Oscillator strengths, Oxidation potentials, Petroleum ether, Phys, Porphyrin, Porphyrin core, Porphyrin rings, Quinoxaline, Quinoxaline linkers, Radical cation, Radical cation species, Redox, Redox processes, Reference compound, Reference compounds, Room temperature, Scan rate, Singlet, Singlet porphyrin, State excitation energy oscillator strength, Subsequent reprecipitation, Supramolecular, Supramolecular triad, Time intervals, Transient spectra, Triad, Verlag, Verlag gmbh, Visible region, Voltammetry, Voltammograms, Weinheim, Weinheim chemphyschem.
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 2 a,b in good yields. These planar and extended π‐conjugated molecules absorb light over a wide region of the UV/Vis 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 2 a,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.
Url:
DOI: 10.1002/cphc.201200350
Affiliations:
- Australie, Corée du Sud, France, Japon, Suisse
- Canton de Berne, Pays de la Loire, Victoria (État)
- Angers, Berne, Melbourne
- Université d'Angers, Université de Berne
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Bhosale , School of Chemistry, Monash University, Clayton, VIC‐3800 (Australia)Shunichi Fukuzumi , Department of Material and Life Science, Graduate School of Engineering, Osaka University, Suita</wicri:regionArea><orgName type="university">Université de Berne</orgName><placeName><settlement type="city">Berne</settlement><region nuts="3" type="region">Canton de Berne</region></placeName></affiliation></author><author><name sortKey="Jaggi, Michael" sort="Jaggi, Michael" uniqKey="Jaggi M" first="Michael" last="Jaggi">Michael Jaggi</name><affiliation wicri:level="4"><orgName type="university">Université de Berne</orgName><country>Suisse</country><placeName><settlement type="city">Berne</settlement><region nuts="3" type="region">Canton de Berne</region></placeName></affiliation></author><author><name sortKey="Monbaron, Philippe" sort="Monbaron, Philippe" uniqKey="Monbaron P" first="Philippe" last="Monbaron">Philippe Monbaron</name><affiliation wicri:level="4"><orgName type="university">Université de Berne</orgName><country>Suisse</country><placeName><settlement type="city">Berne</settlement><region nuts="3" type="region">Canton de Berne</region></placeName></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"><country xml:lang="fr">Australie</country><wicri:regionArea>School of Chemistry, Monash University, Clayton</wicri:regionArea><wicri:noRegion>Clayton</wicri:noRegion></affiliation><affiliation wicri:level="3"><country xml:lang="fr">Australie</country><wicri:regionArea>Current address: School of Applied Sciences, RMIT University, GPO Box 2476V, Melbourne</wicri:regionArea><placeName><settlement type="city">Melbourne</settlement><region type="état">Victoria (État)</region></placeName></affiliation><affiliation></affiliation><affiliation wicri:level="4"><country xml:lang="fr">Japon</country><wicri:regionArea>Shi‐Xia Liu, Departement für Chemie und Biochemie, Universität Bern, Freiestrasse 3, 3012 Bern (Switzerland), Fax: (+41) 31‐631‐3995Sheshanath V. Bhosale , School of Chemistry, Monash University, Clayton, VIC‐3800 (Australia)Shunichi Fukuzumi , Department of Material and Life Science, Graduate School of Engineering, Osaka University, Suita</wicri:regionArea><orgName type="university">Université de Berne</orgName><placeName><settlement type="city">Berne</settlement><region nuts="3" type="region">Canton de Berne</region></placeName></affiliation></author><author><name sortKey="Rivadehi, Shadi" sort="Rivadehi, Shadi" uniqKey="Rivadehi S" first="Shadi" last="Rivadehi">Shadi Rivadehi</name><affiliation wicri:level="1"><country xml:lang="fr">Australie</country><wicri:regionArea>School of Chemistry, Monash University, Clayton</wicri:regionArea><wicri:noRegion>Clayton</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"><country xml:lang="fr">Australie</country><wicri:regionArea>School of Chemistry, Monash University, Clayton</wicri:regionArea><wicri:noRegion>Clayton</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"><country xml:lang="fr">France</country><wicri:regionArea>Institut des Sciences et Technologies Moléculaires d'Angers, Université d'Angers, CNRS UMR 6200, 2 Bd Lavoisier</wicri:regionArea><orgName type="university">Université d'Angers</orgName><placeName><settlement type="city">Angers</settlement><region type="region" nuts="2">Pays de la Loire</region></placeName></affiliation></author><author><name sortKey="Levillain, Eric" sort="Levillain, Eric" uniqKey="Levillain E" first="Eric" last="Levillain">Eric Levillain</name><affiliation wicri:level="4"><country xml:lang="fr">France</country><wicri:regionArea>Institut des Sciences et Technologies Moléculaires d'Angers, Université d'Angers, CNRS UMR 6200, 2 Bd Lavoisier</wicri:regionArea><orgName type="university">Université d'Angers</orgName><placeName><settlement type="city">Angers</settlement><region type="region" nuts="2">Pays de la Loire</region></placeName></affiliation></author><author><name sortKey="El Houly, Mohamed E" sort="El Houly, Mohamed E" uniqKey="El Houly M" first="Mohamed E." last="El-Khouly">Mohamed E. El-Khouly</name><affiliation wicri:level="1"><country xml:lang="fr">Japon</country><wicri:regionArea>Department of Material and Life Science, Graduate School of Engineering, Osaka University, Suita</wicri:regionArea><wicri:noRegion>Suita</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"><country xml:lang="fr">Japon</country><wicri:regionArea>Department of Chemistry, Graduate School of Science, Osaka University, 1‐1 Machikaneyama, Toyonaka</wicri:regionArea><wicri:noRegion>Toyonaka</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"><country xml:lang="fr">Japon</country><wicri:regionArea>Department of Material and Life Science, Graduate School of Engineering, Osaka University, Suita</wicri:regionArea><wicri:noRegion>Suita</wicri:noRegion></affiliation><affiliation wicri:level="1"><country xml:lang="fr">Corée du Sud</country><wicri:regionArea>Department of Bioinspired Science, Ewha Womans University</wicri:regionArea><wicri:noRegion>Ewha Womans University</wicri:noRegion></affiliation><affiliation wicri:level="1"><country wicri:rule="url">Japon</country></affiliation><affiliation wicri:level="4"><country xml:lang="fr">Japon</country><wicri:regionArea>Shi‐Xia Liu, Departement für Chemie und Biochemie, Universität Bern, Freiestrasse 3, 3012 Bern (Switzerland), Fax: (+41) 31‐631‐3995Sheshanath V. Bhosale , School of Chemistry, Monash University, Clayton, VIC‐3800 (Australia)Shunichi Fukuzumi , Department of Material and Life Science, Graduate School of Engineering, Osaka University, Suita</wicri:regionArea><orgName type="university">Université de Berne</orgName><placeName><settlement type="city">Berne</settlement><region nuts="3" type="region">Canton de Berne</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"><orgName type="university">Université de Berne</orgName><country>Suisse</country><placeName><settlement type="city">Berne</settlement><region nuts="3" type="region">Canton de Berne</region></placeName></affiliation></author></analytic><monogr></monogr><series><title level="j" type="main">ChemPhysChem</title><title level="j" type="alt">CHEMPHYSCHEM</title><idno type="ISSN">1439-4235</idno><idno type="eISSN">1439-7641</idno><imprint><biblScope unit="vol">13</biblScope><biblScope unit="issue">14</biblScope><biblScope unit="page" from="3370">3370</biblScope><biblScope unit="page" to="3382">3382</biblScope><biblScope unit="page-count">13</biblScope><publisher>WILEY‐VCH Verlag</publisher><pubPlace>Weinheim</pubPlace><date type="published" when="2012-10-08">2012-10-08</date></imprint><idno type="ISSN">1439-4235</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">1439-4235</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Absorption band</term><term>Absorption spectra</term><term>Acceptor</term><term>Asymmetric dyads</term><term>Benzonitrile</term><term>Bhosale</term><term>Calcd</term><term>Cation</term><term>Charge separation</term><term>Chem</term><term>Chemphyschem</term><term>Crossley</term><term>Crude product</term><term>Cyclic</term><term>Cyclic voltammetry</term><term>Cyclic voltammograms</term><term>Decay profile</term><term>Decurtins</term><term>Differential absorption spectra</term><term>Dominant contributions</term><term>Dyad</term><term>Electrochemical</term><term>Electron transfer</term><term>Elemental analysis calcd</term><term>Excitation</term><term>Femtosecond</term><term>Femtosecond flash photolysis</term><term>First oxidation</term><term>First oxidation process</term><term>Ftir</term><term>Fukuzumi</term><term>Gmbh</term><term>Good agreement</term><term>Homo</term><term>Information figure</term><term>Information figures</term><term>Kgaa</term><term>Levillain</term><term>Lumo</term><term>Molecular structure</term><term>Oscillator</term><term>Oscillator strengths</term><term>Oxidation potentials</term><term>Petroleum ether</term><term>Phys</term><term>Porphyrin</term><term>Porphyrin core</term><term>Porphyrin rings</term><term>Quinoxaline</term><term>Quinoxaline linkers</term><term>Radical cation</term><term>Radical cation species</term><term>Redox</term><term>Redox processes</term><term>Reference compound</term><term>Reference compounds</term><term>Room temperature</term><term>Scan rate</term><term>Singlet</term><term>Singlet porphyrin</term><term>State excitation energy oscillator strength</term><term>Subsequent reprecipitation</term><term>Supramolecular</term><term>Supramolecular triad</term><term>Time intervals</term><term>Transient spectra</term><term>Triad</term><term>Verlag</term><term>Verlag gmbh</term><term>Visible region</term><term>Voltammetry</term><term>Voltammograms</term><term>Weinheim</term><term>Weinheim chemphyschem</term></keywords><keywords scheme="Teeft" xml:lang="en"><term>Absorption band</term><term>Absorption spectra</term><term>Acceptor</term><term>Asymmetric dyads</term><term>Benzonitrile</term><term>Bhosale</term><term>Calcd</term><term>Cation</term><term>Charge separation</term><term>Chem</term><term>Chemphyschem</term><term>Crossley</term><term>Crude product</term><term>Cyclic</term><term>Cyclic voltammetry</term><term>Cyclic voltammograms</term><term>Decay profile</term><term>Decurtins</term><term>Differential absorption spectra</term><term>Dominant contributions</term><term>Dyad</term><term>Electrochemical</term><term>Electron transfer</term><term>Elemental analysis calcd</term><term>Excitation</term><term>Femtosecond</term><term>Femtosecond flash photolysis</term><term>First oxidation</term><term>First oxidation process</term><term>Ftir</term><term>Fukuzumi</term><term>Gmbh</term><term>Good agreement</term><term>Homo</term><term>Information figure</term><term>Information figures</term><term>Kgaa</term><term>Levillain</term><term>Lumo</term><term>Molecular structure</term><term>Oscillator</term><term>Oscillator strengths</term><term>Oxidation potentials</term><term>Petroleum ether</term><term>Phys</term><term>Porphyrin</term><term>Porphyrin core</term><term>Porphyrin rings</term><term>Quinoxaline</term><term>Quinoxaline linkers</term><term>Radical cation</term><term>Radical cation species</term><term>Redox</term><term>Redox processes</term><term>Reference compound</term><term>Reference compounds</term><term>Room temperature</term><term>Scan rate</term><term>Singlet</term><term>Singlet porphyrin</term><term>State excitation energy oscillator strength</term><term>Subsequent reprecipitation</term><term>Supramolecular</term><term>Supramolecular triad</term><term>Time intervals</term><term>Transient spectra</term><term>Triad</term><term>Verlag</term><term>Verlag gmbh</term><term>Visible region</term><term>Voltammetry</term><term>Voltammograms</term><term>Weinheim</term><term>Weinheim chemphyschem</term></keywords></textClass></profileDesc></teiHeader><front><div type="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 2 a,b in good yields. These planar and extended π‐conjugated molecules absorb light over a wide region of the UV/Vis 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 2 a,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.</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>Victoria (État)</li></region><settlement><li>Angers</li><li>Berne</li><li>Melbourne</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="Jia, Hongpeng" sort="Jia, Hongpeng" uniqKey="Jia H" first="Hongpeng" last="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 Ia" sort="Liu, Shi Ia" uniqKey="Liu S" first="Shi-Xia" last="Liu">Shi-Xia Liu</name><name sortKey="Liu, Shi Ia" sort="Liu, Shi Ia" 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="Japon"><region name="Canton de Berne"><name sortKey="Liu, Shi Ia" sort="Liu, Shi Ia" uniqKey="Liu S" first="Shi-Xia" last="Liu">Shi-Xia Liu</name></region><name sortKey="Bhosale, Sheshanath V" sort="Bhosale, Sheshanath V" uniqKey="Bhosale S" first="Sheshanath V." last="Bhosale">Sheshanath V. Bhosale</name><name sortKey="El Houly, Mohamed E" sort="El Houly, Mohamed E" uniqKey="El Houly M" first="Mohamed E." last="El-Khouly">Mohamed E. El-Khouly</name><name sortKey="Fukuzumi, Shunichi" sort="Fukuzumi, Shunichi" uniqKey="Fukuzumi S" first="Shunichi" last="Fukuzumi">Shunichi Fukuzumi</name><name sortKey="Fukuzumi, Shunichi" sort="Fukuzumi, Shunichi" uniqKey="Fukuzumi S" first="Shunichi" last="Fukuzumi">Shunichi Fukuzumi</name><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="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="Bhosale, Sheshanath V" sort="Bhosale, Sheshanath V" uniqKey="Bhosale S" first="Sheshanath V." last="Bhosale">Sheshanath V. Bhosale</name><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="Corée du Sud"><noRegion><name sortKey="Fukuzumi, Shunichi" sort="Fukuzumi, Shunichi" uniqKey="Fukuzumi S" first="Shunichi" last="Fukuzumi">Shunichi Fukuzumi</name></noRegion></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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