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Tetrathiafulvalene and Benzodifuran-based Molecular Scaffoldings: Design and Synthesis of Large pi-conjugated Electro-Active Molecules for Organic (Opto)electronics

English title Tetrathiafulvalene and Benzodifuran-based Molecular Scaffoldings: Design and Synthesis of Large pi-conjugated Electro-Active Molecules for Organic (Opto)electronics
Applicant Decurtins Silvio
Number 147143
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 01.04.2013 - 31.03.2015
Approved amount 438'603.00
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All Disciplines (2)

Discipline
Organic Chemistry
Inorganic Chemistry

Keywords (8)

organic field-effect transistors; supramolecular self-assembly; electron and energy transfer; donor-acceptor ensembles; molecular (opto)electronics; benzodifuran; tetrathiafulvalene; single molecular conductance

Lay Summary (German)

Lead
Die Zielsetzung des Projektes ist, geeignete molekulare Bausteine als Komponenten für elektronische Prozessführungen auf der nanometer Skala zu eruieren. Die Herausforderung ist, effiziente chemische Synthesemethoden für die Zielverbindungen zu finden.
Lay summary
Dieses Nat.-Fonds Projekt befasst sich mit Studien zum Thema der „Molekularen Elektronik“. Im Vordergrund stehen synthetische Arbeiten um neue redox-aktive molekulare Verbindungen herzustellen und analytisch zu charakterisieren. Das heisst, es müssen effiziente synthetische Methoden gefunden werden um die Moleküle in reiner Form und genügender Menge herzustellen. Danach werden die molekularen Systeme im Grundzustand und in elektronisch angeregten Zuständen (Licht-induziert) auf ihre elektronische Leitfähigkeiten (charge transport) untersucht. Die Untersuchungen werden einerseits am amorphen (Film) oder kristallinen makroskopischen Festkörper und andererseits auch auf der nanometer Skala an einzelnen Molekülen vorgenommen. Die Zielsetzung ist, geeignete molekulare Bausteine als Komponenten für elektronische Prozessführungen auf der nanometer Skala zu eruieren.
Direct link to Lay Summary Last update: 27.03.2013

Responsible applicant and co-applicants

Employees

Publications

Publication
Current advances in fused tetrathiafulvalene donor-acceptor systems
Bergkamp Jesse J., Decurtins Silvio, Liu Shi-Xia (2015), Current advances in fused tetrathiafulvalene donor-acceptor systems, in CHEMICAL SOCIETY REVIEWS, 44(4), 863-874.
One-Photon Near-Infrared Sensitization of Well-Defined Yb(III) Surface Complexes for NIR-to-NIR Single Nanoparticle Imaging
Lapadula Giuseppe, Trummer David, Conley Matthew P., Steinmann Martin, Ran Ying-Fen, Brasselet Sophie, Guyot Yannick, Maury Olivier, Decurtins Silvio, Liu Shi-Xia, Coperet Christophe (2015), One-Photon Near-Infrared Sensitization of Well-Defined Yb(III) Surface Complexes for NIR-to-NIR Single Nanoparticle Imaging, in CHEMISTRY OF MATERIALS, 27(6), 2033-2039.
A Compact Tetrathiafulvalene-Benzothiadiazole Dyad and Its Highly Symmetrical Charge-Transfer Salt: Ordered Donor pi-Stacks Closely Bound to Their Acceptors
Geng Yan, Pfattner Raphael, Campos Antonio, Hauser Juerg, Laukhin Vladimir, Puigdollers Joaquim, Veciana Jaume, Mas-Torrent Marta, Rovira Concepcio, Decurtins Silvio, Liu Shi-Xia (2014), A Compact Tetrathiafulvalene-Benzothiadiazole Dyad and Its Highly Symmetrical Charge-Transfer Salt: Ordered Donor pi-Stacks Closely Bound to Their Acceptors, in CHEMISTRY-A EUROPEAN JOURNAL, 20(23), 7136-7143.
A Cruciform Electron Donor-Acceptor Semiconductor with Solid-State Red Emission: 1D/2D Optical Waveguides and Highly Sensitive/Selective Detection of H2S Gas
Luo Hewei, Chen Songjie, Liu Zitong, Zhang Chuang, Cai Zhengxu, Chen Xin, Zhang Guanxin, Zhao Yongsheng, Decurtins Silvio, Liu Shi-Xia, Zhang Deqing (2014), A Cruciform Electron Donor-Acceptor Semiconductor with Solid-State Red Emission: 1D/2D Optical Waveguides and Highly Sensitive/Selective Detection of H2S Gas, in ADVANCED FUNCTIONAL MATERIALS, 24(27), 4250-4258.
A highly sensitive TTF-functionalised probe for the determination of physiological thiols and its application in tumor cells
Wang Wei, Zhao Na, Geng Yan, Cui Shi-Bin, Hauser Juerg, Decurtins Silvio, Liu Shi-Xia (2014), A highly sensitive TTF-functionalised probe for the determination of physiological thiols and its application in tumor cells, in RSC ADVANCES, 4(62), 32639-32642.
A quinoxaline-fused tetrathiafulvalene derivative and its semiconducting charge-transfer salt: synthesis, crystal structures and physical properties
Geng Yan, Fiolka Christoph, Kraemer Karl, Hauser Juerg, Laukhin Vladimir, Decurtins Silvio, Liu Shi-Xia (2014), A quinoxaline-fused tetrathiafulvalene derivative and its semiconducting charge-transfer salt: synthesis, crystal structures and physical properties, in NEW JOURNAL OF CHEMISTRY, 38(5), 2052-2057.
A quinoxaline-fused tetrathiafulvalene-based sensitizer for efficient dye-sensitized solar cells
Amacher Anneliese, Yi Chenyi, Yang Jiabao, Bircher Martin Peter, Fu Yongchun, Cascella Michele, Graetzel Michael, Decurtins Silvio, Liu Shi-Xia (2014), A quinoxaline-fused tetrathiafulvalene-based sensitizer for efficient dye-sensitized solar cells, in CHEMICAL COMMUNICATIONS, 50(49), 6540-6542.
Contrast Formation in Kelvin Probe Force Microscopy of Single pi-Conjugated Molecules
Schuler Bruno, Liu Shi-Xia, Geng Yan, Decurtins Silvio, Meyer Gerhard, Gross Leo (2014), Contrast Formation in Kelvin Probe Force Microscopy of Single pi-Conjugated Molecules, in NANO LETTERS, 14(6), 3342-3346.
Electronic tuning effects via cyano substitution of a fused tetrathiafulvalene-benzothiadiazole dyad for ambipolar transport properties
Amacher Anneliese, Luo Hewei, Liu Zitong, Bircher Martin, Cascella Michele, Hauser Juerg, Decurtins Silvio, Zhang Deqing, Liu Shi-Xia (2014), Electronic tuning effects via cyano substitution of a fused tetrathiafulvalene-benzothiadiazole dyad for ambipolar transport properties, in RSC ADVANCES, 4(6), 2873-2878.
Electronic tuning effects via pi-linkers in tetrathiafulvalene-based dyes
Geng Yan, Pop Flavia, Yi Chenyi, Avarvari Narcis, Graetzel Michael, Decurtins Silvio, Liu Shi-Xia (2014), Electronic tuning effects via pi-linkers in tetrathiafulvalene-based dyes, in NEW JOURNAL OF CHEMISTRY, 38(7), 3269-3274.
HOMO Stabilisation in pi-Extended Dibenzotetrathiafulvalene Derivatives for Their Application in Organic Field-Effect Transistors
Geng Yan, Pfattner Raphael, Campos Antonio, Wang Wei, Jeannin Olivier, Hauser Juerg, Puigdollers Joaquim, Bromley Stefan T., Decurtins Silvio, Veciana Jaume, Rovira Concepcio, Mas-Torrent Marta, Liu Shi-Xia (2014), HOMO Stabilisation in pi-Extended Dibenzotetrathiafulvalene Derivatives for Their Application in Organic Field-Effect Transistors, in CHEMISTRY-A EUROPEAN JOURNAL, 20(50), 16672-16679.
Interpenetrated (8,3)-c and (10,3)-b Metal-Organic Frameworks Based on {Fe-3(III)} and ((Fe2CoII)-Co-III} Pivalate Spin Clusters
Botezat Olga, van Leusen Jan, Kravtsov Victor Ch, Filippova Irina G., Hauser Juerg, Speldrich Manfred, Hermann Raphael P., Kraemer Karl W., Liu Shi-Xia, Decurtins Silvio, Koegerler Paul, Baca Svetlana G. (2014), Interpenetrated (8,3)-c and (10,3)-b Metal-Organic Frameworks Based on {Fe-3(III)} and ((Fe2CoII)-Co-III} Pivalate Spin Clusters, in CRYSTAL GROWTH & DESIGN, 14(9), 4721-4728.
Large pi-Conjugated Chromophores Derived from Tetrathiafulvalene
Jia Hongpeng, Ding Jie, Hauser Andreas, Decurtins Silvio, Liu Shi-Xia (2014), Large pi-Conjugated Chromophores Derived from Tetrathiafulvalene, in ASIAN JOURNAL OF ORGANIC CHEMISTRY, 3(2), 198-202.
Mixed-ligand hydroxocopper(II)/pyridazine clusters embedded into 3D framework lattices
Degtyarenko Anna S., Handke Marcel, Kraemer Karl W., Liu Shi-Xia, Decurtins Silvio, Rusanov Eduard B., Thompson Laurence K., Krautscheid Harald, Domasevitch Konstantin V. (2014), Mixed-ligand hydroxocopper(II)/pyridazine clusters embedded into 3D framework lattices, in DALTON TRANSACTIONS, 43(22), 8530-8542.
Regulating a Benzodifuran Single Molecule Redox Switch via Electrochemical Gating and Optimization of Molecule/Electrode Coupling
Li Zhihai, Li Hui, Chen Songjie, Froehlich Toni, Yi Chenyi, Schoenenberger Christian, Calame Michel, Decurtins Silvio, Liu Shi-Xia, Borguet Eric (2014), Regulating a Benzodifuran Single Molecule Redox Switch via Electrochemical Gating and Optimization of Molecule/Electrode Coupling, in JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 136(25), 8867-8870.
Tetracarboxylate Ligands as New Chelates Supporting Copper(II) Paddlewheel-Like Structures
Gomila Antoine, Duval Sylvain, Besnard Celine, Kraemer Karl W., Liu Shi-Xia, Decurtins Silvio, Williams Alan F. (2014), Tetracarboxylate Ligands as New Chelates Supporting Copper(II) Paddlewheel-Like Structures, in INORGANIC CHEMISTRY, 53(5), 2683-2691.
The coordination chemistry of tartronic acid with copper: magnetic studies of a quasi-equilateral tricopper triangle
Pascu Gabriel, Deville Claire, Clifford Sarah E., Guenee Laure, Besnard Celine, Kraemer Karl W., Liu Shi-Xia, Decurtins Silvio, Tuna Floriana, McInnes Eric J. L., Winpenny Richard E. P., Williams Alan F. (2014), The coordination chemistry of tartronic acid with copper: magnetic studies of a quasi-equilateral tricopper triangle, in DALTON TRANSACTIONS, 43(2), 656-662.
The Metallofullerene Field-Induced Single-Ion Magnet HoSc2N@C-80
Dreiser Jan, Westerstrom Rasmus, Zhang Yang, Popov Alexey A., Dunsch Lothar, Kraemer Karl, Liu Shi-Xia, Decurtins Silvio, Greber Thomas (2014), The Metallofullerene Field-Induced Single-Ion Magnet HoSc2N@C-80, in CHEMISTRY-A EUROPEAN JOURNAL, 20(42), 13536-13540.
Triazolyl-Based Copper-Molybdate Hybrids: From Composition Space Diagram to Magnetism and Catalytic Performance
Senchyk Ganna A., Lysenko Andrey B., Babaryk Artem A., Rusanov Eduard B., Krautscheid Harald, Neves Patricia, Valente Anabela A., Goncalves Isabel S., Kraemer Karl W., Liu Shi-Xia, Decurtins Silvio, Domasevitch Konstantin V. (2014), Triazolyl-Based Copper-Molybdate Hybrids: From Composition Space Diagram to Magnetism and Catalytic Performance, in INORGANIC CHEMISTRY, 53(19), 10112-10121.

Associated projects

Number Title Start Funding scheme
130266 Tetrathiafulvalene- and benzodifuran-based ligands as building blocks for multifunctional magneto- and optoelectronic materials: A synthetic study. 01.04.2010 Project funding (Div. I-III)

Abstract

Interest in organic (opto)electronics stems not only from the possibility to produce low-cost, large-area, lightweight and flexible devices, but also from their intrinsic properties, such as low-temperature device fabrication, versatility of chemical synthesis, and ease of processing. Within this context, tetrathiafulvalene(TTF)- and benzodifuran (BDF)-based compounds have received tremendous attention due to their fascinating redox and optical properties. They are of particular importance in the development of molecular (opto)electronics such as organic conductive materials, nonlinear optical (NLO) materials, near-infrared dyes, molecular wires, organic light emitting diodes (OLEDs), sensors, organic field effect transistors (OFETs) and solar cells. In the most cases, the device performance depends critically on how easily electrons or holes drift through a semiconductor in response to an electric field. As a continuation of our current research work, this actual project aims to obtain a range of large pi-conjugated electro-active molecules by the judicious design and appropriate functionalization of TTF- and BDF-cores, as illustrated in the following Scheme. A crucial issue concerns the optimal way to link the various components leading to excellent charge carrier mobility and high stability of the resultant organic materials. Different synthetic methodologies for new solution-processed small organic molecules and also pi-conjugated polymers with TTF or BDF units on their backbone or side chains will be explored. Both experimental and theoretical investigations will be carried out to gain insight of the charge transport mechanisms and the structure-mobility relationship. These timely issues remain an extremely complex subject. We believe that our proposed work can facilitate the rational design of new promising organic semiconductors, particularly for organic light-emitting transistors.
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