Project

Back to overview

Tetrathiafulvalene- and benzodifuran-based ligands as building blocks for multifunctional magneto- and optoelectronic materials: A synthetic study.

English title Tetrathiafulvalene- and benzodifuran-based ligands as building blocks for multifunctional magneto- and optoelectronic materials: A synthetic study.
Applicant Decurtins Silvio
Number 130266
Funding scheme Project funding (Div. I-III)
Research institution Departement für Chemie und Biochemie Universität Bern
Institution of higher education University of Berne - BE
Main discipline Organic Chemistry
Start/End 01.04.2010 - 31.03.2013
Approved amount 512'741.00
Show all

All Disciplines (2)

Discipline
Organic Chemistry
Inorganic Chemistry

Keywords (10)

donor-acceptor ensembles; tetrathiafulvalene; benzodifuran; molecular (opto)electronics; electron and energy transfer; supramolecular self-assembly; Synthesis; redox-active molecular systems; chromophores; photophysics

Lay Summary (English)

Lead
Lay summary
Tetrathiafulvalene- and benzodifuran-based compounds are of particular interest due to their exceptional (opto)electronic properties. A wide variety of pi-conjugated multichromophoric donor-acceptor ensembels will be synthesized for studying in depth photo-induced electron- and energy transfer as well as the photogeneration of long-lived charge separated states. Different synthetic strategies will be explored and additionally, oligo- and polymerization reactions will be probed. Such donor-acceptor systems can play a crucial role in an approach to molecular (opto)electronics with high-efficiency.
Direct link to Lay Summary Last update: 21.02.2013

Responsible applicant and co-applicants

Employees

Publications

Publication
A Pt(II) complex with both a phenanthroline and a tetrathiafulvalene-extended dithiolate ligand: Synthesis, crystal structure, electrochemical and spectroscopic properties
Jia Chunyang, Ding Jie, Liu Shi-Xia, Labat Gaël, Neels Antonia, Hauser Andreas, Decurtins Silvio (2013), A Pt(II) complex with both a phenanthroline and a tetrathiafulvalene-extended dithiolate ligand: Synthesis, crystal structure, electrochemical and spectroscopic properties, in Polyhedron, 55, 87-91.
Synthesis and Redox and Photophysical Properties of Benzodifuran–Spiropyran Ensembles
Li Hui, Ding Jie, Chen Songjie, Beyer Christoph, Liu Shi-Xia, Wagenknecht Hans-Achim, Hauser Andreas, Decurtins Silvio (2013), Synthesis and Redox and Photophysical Properties of Benzodifuran–Spiropyran Ensembles, in Chemistry – A European Journal, 19(20), 6459-6466.
Two-Dimensional Supramolecular Electron Spin Arrays
Wäckerlin Christian, Nowakowski Jan, Liu Shi-Xia, Jaggi Michael, Siewert Dorota, Girovsky Jan, Shchyrba Aneliia, Hählen Tatjana, Kleibert Armin, Oppeneer Peter M., Nolting Frithjof, Decurtins Silvio, Jung Thomas A., Ballav Nirmalya (2013), Two-Dimensional Supramolecular Electron Spin Arrays, in Advanced Materials, 25(17), 2404-2408.
New copper(II) complexes with isoconazole: Synthesis, structures and biological properties
Dulcevscaia Galina M., Kravtsov Victor Ch, Macaev Fliur Z., Duca Gheorghe G., Stingachi Eugenia P., Pogrebnoi Serghei I., Boldescu Veaceslav V., Clapco Steliana F., Tiurina Janeta P., Deseatnic-Ciloci Alexandra A., Lipkowski Janusz, Liu Shi-Xia, Decurtins Silvio, Baca Svetlana G. (2013), New copper(II) complexes with isoconazole: Synthesis, structures and biological properties, in Polyhedron, 52, 106-114.
Tetrathiafulvalene-Benzothiadiazoles as Redox-Tunable Donor–Acceptor Systems: Synthesis and Photophysical Study
Pop Flavia, Amacher Anneliese, Avarvari Narcis, Ding Jie, Daku Latevi Max Lawson, Hauser Andreas, Koch Marius, Hauser Jürg, Liu Shi-Xia, Decurtins Silvio (2013), Tetrathiafulvalene-Benzothiadiazoles as Redox-Tunable Donor–Acceptor Systems: Synthesis and Photophysical Study, in Chemistry – A European Journal, 19(7), 2504-2514.
Functionalized Adamantane Tectons Used in the Design of Mixed-Ligand Copper(II) 1,2,4-Triazolyl/Carboxylate Metal–Organic Frameworks
Senchyk Ganna A., Lysenko Andrey B., Krautscheid Harald, Rusanov Eduard B., Chernega Alexander N., Krämer Karl W., Liu Shi-Xia, Decurtins Silvio, Domasevitch Konstantin V. (2013), Functionalized Adamantane Tectons Used in the Design of Mixed-Ligand Copper(II) 1,2,4-Triazolyl/Carboxylate Metal–Organic Frameworks, in Inorganic Chemistry, 52(2), 863-872.
A Donor–Acceptor Tetrathiafulvalene Ligand Complexed to Iron(II): Synthesis, Electrochemistry, and Spectroscopy of [Fe(phen)2(TTF-dppz)](PF6)2
Dupont Nathalie, Ran Ying-Fen, Liu Shi-Xia, Grilj Jakob, Vauthey Eric, Decurtins Silvio, Hauser Andreas (2013), A Donor–Acceptor Tetrathiafulvalene Ligand Complexed to Iron(II): Synthesis, Electrochemistry, and Spectroscopy of [Fe(phen)2(TTF-dppz)](PF6)2, in Inorganic Chemistry, 52(1), 306-312.
Trimethylsilyl-Terminated Oligo(phenylene ethynylene)s: An Approach to Single-Molecule Junctions with Covalent Au-C σ-Bonds
Hong Wenjing, Li Hui, Liu Shi-Xia, Fu Yongchun, Li Jianfeng, Kaliginedi Veerabhadrarao, Decurtins Silvio, Wandlowski Thomas (2012), Trimethylsilyl-Terminated Oligo(phenylene ethynylene)s: An Approach to Single-Molecule Junctions with Covalent Au-C σ-Bonds, in J. Am. Chem. Soc., 134(47), 19425-19431.
A Spectroscopic and Computational Study of a Photoinduced Cross-Dehydrogenative Coupling Reaction of a Stable Semiquinone Radical
Grilj Jakob, Todorova Tanya Kumanova, Yi Chenyi, Liu Shi-Xia, Vauthey Eric, Decurtins Silvio (2012), A Spectroscopic and Computational Study of a Photoinduced Cross-Dehydrogenative Coupling Reaction of a Stable Semiquinone Radical, in Chem.--Eur. J., 18(43), 13605-13608.
Tetrathiafulvalene-Fused Porphyrins via Quinoxaline Linkers: Symmetric and Asymmetric Donor-Acceptor Systems
Jia Hongpeng, Schmid Belinda, Liu Shi-Xia, Jaggi Michael, Monbaron Philippe, Bhosale Sheshanath V., Rivadehi Shadi, Langford Steven J., Sanguinet Lionel, Levillain Eric, El-Khouly Mohamed E., Morita Ysushi, Fukuzumi Shunichi, Decurtins Silvio (2012), Tetrathiafulvalene-Fused Porphyrins via Quinoxaline Linkers: Symmetric and Asymmetric Donor-Acceptor Systems, in ChemPhysChem, 13(14), 3370-3382.
Tetrathiafulvalene-based lanthanide coordination complexes: Synthesis, crystal structure, optical and electrochemical characterization
Ran Ying-Fen, Steinmann Martin, Sigrist Marc, Liu Shi-Xia, Hauser Jürg, Decurtins Silvio (2012), Tetrathiafulvalene-based lanthanide coordination complexes: Synthesis, crystal structure, optical and electrochemical characterization, in C. R. Chim., 15(10), 838-844.
[V16O38(CN)]9-: A Soluble Mixed-Valence Redox-Active Building Block with Strong Antiferromagnetic Coupling
Keene Tony D., D'Alessandro Deanna M., Krämer Karl W., Price Jason R., Price David J., Decurtins Silvio, Kepert Cameron J. (2012), [V16O38(CN)]9-: A Soluble Mixed-Valence Redox-Active Building Block with Strong Antiferromagnetic Coupling, in Inorg. Chem., 51(17), 9192-9199.
Synthesis, Structure, and Properties of the New Mixed-Valent Dodecahalogenotrimetallate In4Ti3Br12 and its Relation to Compounds A3Ti2X9 (A = K, In; X = Cl, Br)
Schroeder Melanie, Hartwig Sabina, Krämer Karl W., Decurtins Silvio, Hillebrecht Harald (2012), Synthesis, Structure, and Properties of the New Mixed-Valent Dodecahalogenotrimetallate In4Ti3Br12 and its Relation to Compounds A3Ti2X9 (A = K, In; X = Cl, Br), in Inorg. Chem., 51(15), 8385-8393.
Phthalate-Based Coordination Polymers
Baca Svetlana G., Decurtins Silvio (2012), Phthalate-Based Coordination Polymers, Nova Publishers, Hauppauge, USA, 1-59.
Benzodifuran-containing well-defined pi-conjugated polymers for photovoltaic cells
Li Hui, Tang Peng, Zhao Yan, Liu Shi-Xia, Aeschi Yves, Deng Lijun, Braun Jörg, Zhao Bin, Liu Yunqi, Tan Songting, Meier Wolfgang, Decurtins Silvio (2012), Benzodifuran-containing well-defined pi-conjugated polymers for photovoltaic cells, in J. Polym. Sci., Part A: Polym. Chem., 50(14), 2935-2943.
Cluster-Based Networks: 1D and 2D Coordination Polymers Based on {MnFe2(μ3-O)}-Type Clusters
Dulcevscaia Galina M., Filippova Irina G., Speldrich Manfred, van Leusen Jan, Kravtsov Victor Ch., Baca Svetlana G., Kögerler Paul, Liu Shi-Xia, Decurtins Silvio (2012), Cluster-Based Networks: 1D and 2D Coordination Polymers Based on {MnFe2(μ3-O)}-Type Clusters, in Inorg. Chem., 51(9), 5110-5117.
Tetrathiafulvalene-annulated dipyrrolylquinoxaline: the effect of fluoride on its optical and electrochemical behaviors
Jia Hong-Peng, Forgie John C., Liu Shi-Xia, Sanguinet Lionel, Levillain Eric, Le Derf Franck, Sallé Marc, Neels Antonia, Skabara Peter J., Decurtins Silvio (2011), Tetrathiafulvalene-annulated dipyrrolylquinoxaline: the effect of fluoride on its optical and electrochemical behaviors, in TETRAHEDRON, 68(5), 1590-1594.
2,3-Dichloro-1,4-hydroquinone 2,3-dichloro-1,4-benzoquinone monohydrate: a quinhydrone-type 1:1 donor-acceptor [D-A] charge-transfer complex
Guegano Xavier, Hauser Juerg, Liu Shi-Xia, Decurtins Silvio (2011), 2,3-Dichloro-1,4-hydroquinone 2,3-dichloro-1,4-benzoquinone monohydrate: a quinhydrone-type 1:1 donor-acceptor [D-A] charge-transfer complex, in ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 67(Part 11), o2967-o2968.
Targeting pi-Conjugated Multiple Donor-Acceptor Motifs Exemplified by Tetrathia-fulvalene (TTF)-Linked Quinoxalines and Tetrabenz[bc,ef,hi,uv]ovalenes: Synthesis, Spectroscopic, Electrochemical, ...
Jia Hong-Peng, Ding Jie, Ran Ying-Fen, Liu Shi-Xia, Blum Carmen, Petkova Irina, Hauser Andreas, Decurtins Silvio (2011), Targeting pi-Conjugated Multiple Donor-Acceptor Motifs Exemplified by Tetrathia-fulvalene (TTF)-Linked Quinoxalines and Tetrabenz[bc,ef,hi,uv]ovalenes: Synthesis, Spectroscopic, Electrochemical, ..., in CHEMISTRY-AN ASIAN JOURNAL, 6(12), 3312-3321.
A tetrathiafulvalene-functionalized naphthalene diimide: synthesis, electrochemical and photophysical properties
Jaggi Michael, Schmid Belinda, Liu Shi-Xia, Bhosale Sheshanath V., Rivadehi Shadi, Langford Steven J., Decurtins Silvio (2011), A tetrathiafulvalene-functionalized naphthalene diimide: synthesis, electrochemical and photophysical properties, in TETRAHEDRON, 67(38), 7231-7235.
Exploratory studies on coordination chemistry of a redox-active bridging ligand: synthesis, properties and solid state structures of the complexes
Ran Ying-Fen, Liu Shi-Xia, Sereda Olha, Neels Antonia, Decurtins Silvio (2011), Exploratory studies on coordination chemistry of a redox-active bridging ligand: synthesis, properties and solid state structures of the complexes, in DALTON TRANSACTIONS, 40(32), 8193-8198.
Synthesis, structures, redox and photophysical properties of benzodifuran-functionalised pyrene and anthracene fluorophores
Keller Stephan, Yi Chenyi, Li Chen, Liu Shi-Xia, Blum Carmen, Frei Gabriela, Sereda Olha, Neels Antonia, Wandlowski Thomas, Decurtins Silvio (2011), Synthesis, structures, redox and photophysical properties of benzodifuran-functionalised pyrene and anthracene fluorophores, in ORGANIC & BIOMOLECULAR CHEMISTRY, 9(18), 6410-6416.
Annulation of Tetrathiafulvalene to the Bay Region of Perylenediimide: Fast Electron-Transfer Processes in Polar and Nonpolar Solvents
El-Khouly Mohamed E., Jaggi Michael, Schmid Belinda, Blum Carmen, Liu Shi-Xia, Decurtins Silvio, Ohkubo Kei, Fukuzumi Shunichi (2011), Annulation of Tetrathiafulvalene to the Bay Region of Perylenediimide: Fast Electron-Transfer Processes in Polar and Nonpolar Solvents, in JOURNAL OF PHYSICAL CHEMISTRY C, 115(16), 8325-8334.
Effect of the Addition of a Fused Donor-Acceptor Ligand on a Ru(II) Complex: Synthesis, Characterization, and Photoinduced Electron Transfer Reactions of [Ru(TTF-dppz)2(Aqphen)]2+
Dupont Nathalie, Ran Ying-Fen, Jia Hong-Peng, Grilj Jakob, Ding Jie, Liu Shi-Xia, Decurtins Silvio, Hauser Andreas (2011), Effect of the Addition of a Fused Donor-Acceptor Ligand on a Ru(II) Complex: Synthesis, Characterization, and Photoinduced Electron Transfer Reactions of [Ru(TTF-dppz)2(Aqphen)]2+, in INORGANIC CHEMISTRY, 50(8), 3295-3303.
Orientation dependent molecular friction on organic layer compound crystals
Fessler Gregor, Zimmermann Iwan, Glatzel Thilo, Gnecco Enrico, Steiner Pascal, Keene Tony D., Liu Shi-Xia, Decurtins Silvio, Meyer Ernst (2011), Orientation dependent molecular friction on organic layer compound crystals, in APPLIED PHYSICS LETTERS, 98(8), 083119-1-083119-3.
A tetrathiafulvalene-functionalized schiff base macrocycle: synthesis, electrochemical, and photophysical properties
Ran Ying-Fen, Blum Carmen, Liu Shi-Xia, Sanguinet Lionel, Levillain Eric, Decurtins Silvio (2011), A tetrathiafulvalene-functionalized schiff base macrocycle: synthesis, electrochemical, and photophysical properties, in TETRAHEDRON, 67(9), 1623-1627.
Two-Dimensional Manganese(II) Coordination Polymer Based on Phthalate and Pyrazine Bridges Exhibiting Antiferromagnetic Porperties
Gherco O., Keene Tony D., Filippova Irina G., Baca Svetlana G., Decurtins Silvio (2011), Two-Dimensional Manganese(II) Coordination Polymer Based on Phthalate and Pyrazine Bridges Exhibiting Antiferromagnetic Porperties, in Moldavian Journal of the Physical Sciences, 10(1), 103-108.
Iron(III)-Pivalate-Based Complexes with Tetranuclear {Fe4(μ3-O)2}8+ Cores and N-Donor Ligands: Formation of Cluster and Polymeric Architectures
Baca Svetlana G., Filippova Irina G., Keene Tony D., Botezat Olga, Malaestean Iurii L., Stoeckli-Evans Helen, Kravtsov Victor Ch., Chumacov Iurii, Liu Shi-Xia, Decurtins Silvio (2010), Iron(III)-Pivalate-Based Complexes with Tetranuclear {Fe4(μ3-O)2}8+ Cores and N-Donor Ligands: Formation of Cluster and Polymeric Architectures, in EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, (3), 356-367.
Benzodifuran-Based pi-Conjugated Copolymers for Bulk Heterojunction Solar Cells
Li Hui, Jiang Peng, Yi Chenyi, Li Chen, Liu Shi-Xia, Tan Songting, Zhao Bin, Braun Jörg, Meier Wolfgang, Wandlowski Thomas, Decurtins Silvio (2010), Benzodifuran-Based pi-Conjugated Copolymers for Bulk Heterojunction Solar Cells, in MACROMOLECULES, 43(19), 8058-8062.
A Scanning Probe Microscopy Study of Annulated Redox-Active Molecules at a Liquid/Solid Interface: The Overruling of the Alkyl Chain Paradigm
Liu Bo, Ran Ying-Fen, Li Zhihai, Liu Shi-Xia, Jia Chunyang, Decurtins Silvio, Wandlowski Thomas (2010), A Scanning Probe Microscopy Study of Annulated Redox-Active Molecules at a Liquid/Solid Interface: The Overruling of the Alkyl Chain Paradigm, in CHEMISTRY-A EUROPEAN JOURNAL, 16(17), 5008-5012.
Versatile Strategy To Access Fully Functionalized Benzodifurans: Redox-Active Chromophores for the Construction of Extended pi-Conjugated Materials
Yi Chenyi, Blum Carmen, Lehmann Mario, Keller Stephan, Liu Shi-Xia, Frei Gabriela, Neels Antonia, Hauser Jürg, Schürch Stefan, Decurtins Silvio (2010), Versatile Strategy To Access Fully Functionalized Benzodifurans: Redox-Active Chromophores for the Construction of Extended pi-Conjugated Materials, in JOURNAL OF ORGANIC CHEMISTRY, 75(10), 3350-3357.
Heterocyclic amine directed synthesis of metal(II)-oxalates: investigating the magnetic properties of two complete series of chains with S=5/2 to S=1/2
Keene Tony D., Zimmermann Iwan, Neels Antonia, Sereda Olha, Hauser Juerg, Bonin Michel, Hursthouse Michael B., Price Daniel J., Decurtins Silvio (2010), Heterocyclic amine directed synthesis of metal(II)-oxalates: investigating the magnetic properties of two complete series of chains with S=5/2 to S=1/2, in DALTON TRANSACTIONS, 39(20), 4937-4950.
Crystal Engineering of a Series of Arylammonium Copper(II) Malonates
Keene Tony D., Zimmermann Iwan, Neels Antonia, Sereda Olha, Hauser Jürg, Liu Shi-Xia, Decurtins Silvio (2010), Crystal Engineering of a Series of Arylammonium Copper(II) Malonates, in CRYSTAL GROWTH & DESIGN, 10(4), 1854-1859.
Photo-Induced Intramolecular Charge Transfer in an Ambipolar Field-Effect Transistor Based on a pi-Conjugated Donor-Acceptor Dyad
Pfattner Raphael, Pavlica Egon, Liu Shi-Xia, Jaggi Michael, Decurtins Silvio, Bratina Gvido, Veciana Jaume, Mas-Torrent Marta, Rovira Concepcio, Photo-Induced Intramolecular Charge Transfer in an Ambipolar Field-Effect Transistor Based on a pi-Conjugated Donor-Acceptor Dyad, in Journal of Materials Chemistry C.

Associated projects

Number Title Start Funding scheme
147143 Tetrathiafulvalene and Benzodifuran-based Molecular Scaffoldings: Design and Synthesis of Large pi-conjugated Electro-Active Molecules for Organic (Opto)electronics 01.04.2013 Project funding (Div. I-III)
116003 Functionalization of Tetrathiafulvalenes (TTFs) toward Artificial Molecular Devices 01.04.2007 Project funding (Div. I-III)

Abstract

Tetrathiafulvalene(TTF)- and benzodifuran (BDF)-based compounds are of particular interest due to their exceptional (opto)electronic properties. This actual project aims to create a very specific and fascinating range of TTF- and BDF-incorporated molecular building blocks that can be programmed not only to ensure their self-assembly into a structurally organized system but also to ensure their functional integration. A wide variety of p-conjugated multichromophoric donor-acceptor (D-A) ensembles will be synthesized for studying in depth photo-induced electron and energy transfer as well as the photogeneration of long-lived charge separated states. A crucial issue concerns the optimal way to interlock the various components (chromophores, conductor, electronic relays ...) into ordered arrays that allows them to efficiently perform specific functions - wires, motors, diodes, rectifiers, antennas, and so on. Different synthetic strategies either based on the covalent linkage or the selective metal-ligand binding interaction will be explored. In addition, oligo- and polymerization reactions will be probed in order to introduce these functional units into the backbone or the side chains of polymers. We believe that such D-A systems can play a crucial role in an approach to molecular (opto)electronics with a high-efficiency.
-