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A. Taticchi - One of the best experts on this subject based on the ideXlab platform.
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Solution-Processable Low-Molecular Weight Extended Arylacetylenes: Versatile p-Type Semiconductors for Field-Effect Transistors and Bulk Heterojunction Solar Cells
Journal of the American Chemical Society, 2010Co-Authors: Fabio Silvestri, Assunta Marrocchi, Mirko Seri, Choongik Kim, Tobin J. Marks, Antonio Facchetti, A. TaticchiAbstract:We report the synthesis and characterization of a series of five extended arylacetylenes, 9,10-bis-{[m,p-bis(hexyloxy)phenyl]ethynyl}-anthracene (A-P6t, 1), 9,10-bis-[(p-{[m,p-bis(hexyloxy) phenyl]ethynyl}phenyl)ethynyl]-anthracene (PA-P6t, 2), 4,7-bis-{[m,p-bis(hexyloxy)phenyl]ethynyl}-2,1,3-Benzothiadiazole (BTZ-P6t, 5), 4,7-bis(5-{[m,p-bis(hexyloxy)phenyl]ethynyl}thien-2-yl)-2,1,3-Benzothiadiazole (TBTZ-P6t, 6), and 7,7'-({[m,p-bis(hexyloxy)phenyl]ethynyl}-2,1,3-benzothiadiazol-4,4'-ethynyl)-2,5-thiophene (BTZT-P6t, 7), and two arylvinylenes, 9,10-bis-{(E)-[m,p-bis(hexyloxy)phenyl]vinyl}-anthracene (A-P6d, 3), 9,10-bis-[(E)-(p-{(E)-[m,p-bis(hexyloxy)phenyl]vinyl}phenyl)vinyl]-anthracene (PA-P6d, 4). Trends in optical absorption spectra and electrochemical redox processes are first described. Next, the thin-film microstructures and morphologies of films deposited from solution under various conditions are investigated, and organic field-effect transistors (OFETs) and bulk heterojunction photovoltaic (OPV) cells fabricated. We find that substituting acetylenic for olefinic linkers on the molecular cores significantly enhances device performance. OFET measurements reveal that all seven of the semiconductors are FET-active and, depending on the backbone architecture, the arylacetylenes exhibit good p-type mobilities (mu up to approximately 0.1 cm(2) V(-1) s(-1)) when optimum film microstructural order is achieved. OPV cells using [6,6]-phenyl C(61)-butyric acid methyl ester (PCBM) as the electron acceptor exhibit power conversion efficiencies (PCEs) up to 1.3% under a simulated AM 1.5 solar irradiation of 100 mW/cm(2). These results demonstrate that arylacetylenes are promising hole-transport materials for p-channel OFETs and promising donors for organic solar cells applications. A direct correlation between OFET arylacetylene hole mobility and OPV performance is identified and analyzed.
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solution processable low molecular weight extended arylacetylenes versatile p type semiconductors for field effect transistors and bulk heterojunction solar cells
Journal of the American Chemical Society, 2010Co-Authors: Fabio Silvestri, Assunta Marrocchi, Mirko Seri, Choongik Kim, Tobin J. Marks, Antonio Facchetti, A. TaticchiAbstract:We report the synthesis and characterization of a series of five extended arylacetylenes, 9,10-bis-{[m,p-bis(hexyloxy)phenyl]ethynyl}-anthracene (A-P6t, 1), 9,10-bis-[(p-{[m,p-bis(hexyloxy) phenyl]ethynyl}phenyl)ethynyl]-anthracene (PA-P6t, 2), 4,7-bis-{[m,p-bis(hexyloxy)phenyl]ethynyl}-2,1,3-Benzothiadiazole (BTZ-P6t, 5), 4,7-bis(5-{[m,p-bis(hexyloxy)phenyl]ethynyl}thien-2-yl)-2,1,3-Benzothiadiazole (TBTZ-P6t, 6), and 7,7′-({[m,p-bis(hexyloxy)phenyl]ethynyl}-2,1,3-benzothiadiazol-4,4′-ethynyl)-2,5-thiophene (BTZT-P6t, 7), and two arylvinylenes, 9,10-bis-{(E)-[m,p-bis(hexyloxy)phenyl]vinyl}-anthracene (A-P6d, 3), 9,10-bis-[(E)-(p-{(E)-[m,p-bis(hexyloxy)phenyl]vinyl}phenyl)vinyl]-anthracene (PA-P6d, 4). Trends in optical absorption spectra and electrochemical redox processes are first described. Next, the thin-film microstructures and morphologies of films deposited from solution under various conditions are investigated, and organic field-effect transistors (OFETs) and bulk heterojunction photovoltaic (OP...
Assunta Marrocchi - One of the best experts on this subject based on the ideXlab platform.
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Photobehavior and Nonlinear Optical Properties of Push–Pull, Symmetrical, and Highly Fluorescent Benzothiadiazole Derivatives
The Journal of Physical Chemistry C, 2016Co-Authors: Federica Ricci, Assunta Marrocchi, Fausto Elisei, Paolo Foggi, Anna Spalletti, Benedetta CarlottiAbstract:Three quadrupolar D−π–A−π–D compounds, bearing alkoxy phenyls as mild electron donors and a Benzothiadiazole (A), two Benzothiadiazoles (B), or a Benzothiadiazole linked to two thiophenes (C) as the acceptor units, are collectively the object of this study. They proved to be efficient yellow/orange/red fluorophores, respectively, with fluorescence being their preferred deactivation pathway. These systems exhibited positive fluorosolvatochromism and a noticeable decrease of the fluorescence quantum yield in the most polar solvent (with the quenching following the trend B > A > C). These findings point to an intramolecular charge transfer (ICT) nature of the emitting state, whose photoinduced dynamics was investigated by femtosecond-resolved transient absorption and fluorescence upconversion. Remarkable values of hyperpolarizability were estimated by the solvatochromic method. The significant two-photon absorption cross sections measured for A–C (whose trend nicely parallels that of ICT efficiency), coupled...
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Solution-Processable Low-Molecular Weight Extended Arylacetylenes: Versatile p-Type Semiconductors for Field-Effect Transistors and Bulk Heterojunction Solar Cells
Journal of the American Chemical Society, 2010Co-Authors: Fabio Silvestri, Assunta Marrocchi, Mirko Seri, Choongik Kim, Tobin J. Marks, Antonio Facchetti, A. TaticchiAbstract:We report the synthesis and characterization of a series of five extended arylacetylenes, 9,10-bis-{[m,p-bis(hexyloxy)phenyl]ethynyl}-anthracene (A-P6t, 1), 9,10-bis-[(p-{[m,p-bis(hexyloxy) phenyl]ethynyl}phenyl)ethynyl]-anthracene (PA-P6t, 2), 4,7-bis-{[m,p-bis(hexyloxy)phenyl]ethynyl}-2,1,3-Benzothiadiazole (BTZ-P6t, 5), 4,7-bis(5-{[m,p-bis(hexyloxy)phenyl]ethynyl}thien-2-yl)-2,1,3-Benzothiadiazole (TBTZ-P6t, 6), and 7,7'-({[m,p-bis(hexyloxy)phenyl]ethynyl}-2,1,3-benzothiadiazol-4,4'-ethynyl)-2,5-thiophene (BTZT-P6t, 7), and two arylvinylenes, 9,10-bis-{(E)-[m,p-bis(hexyloxy)phenyl]vinyl}-anthracene (A-P6d, 3), 9,10-bis-[(E)-(p-{(E)-[m,p-bis(hexyloxy)phenyl]vinyl}phenyl)vinyl]-anthracene (PA-P6d, 4). Trends in optical absorption spectra and electrochemical redox processes are first described. Next, the thin-film microstructures and morphologies of films deposited from solution under various conditions are investigated, and organic field-effect transistors (OFETs) and bulk heterojunction photovoltaic (OPV) cells fabricated. We find that substituting acetylenic for olefinic linkers on the molecular cores significantly enhances device performance. OFET measurements reveal that all seven of the semiconductors are FET-active and, depending on the backbone architecture, the arylacetylenes exhibit good p-type mobilities (mu up to approximately 0.1 cm(2) V(-1) s(-1)) when optimum film microstructural order is achieved. OPV cells using [6,6]-phenyl C(61)-butyric acid methyl ester (PCBM) as the electron acceptor exhibit power conversion efficiencies (PCEs) up to 1.3% under a simulated AM 1.5 solar irradiation of 100 mW/cm(2). These results demonstrate that arylacetylenes are promising hole-transport materials for p-channel OFETs and promising donors for organic solar cells applications. A direct correlation between OFET arylacetylene hole mobility and OPV performance is identified and analyzed.
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solution processable low molecular weight extended arylacetylenes versatile p type semiconductors for field effect transistors and bulk heterojunction solar cells
Journal of the American Chemical Society, 2010Co-Authors: Fabio Silvestri, Assunta Marrocchi, Mirko Seri, Choongik Kim, Tobin J. Marks, Antonio Facchetti, A. TaticchiAbstract:We report the synthesis and characterization of a series of five extended arylacetylenes, 9,10-bis-{[m,p-bis(hexyloxy)phenyl]ethynyl}-anthracene (A-P6t, 1), 9,10-bis-[(p-{[m,p-bis(hexyloxy) phenyl]ethynyl}phenyl)ethynyl]-anthracene (PA-P6t, 2), 4,7-bis-{[m,p-bis(hexyloxy)phenyl]ethynyl}-2,1,3-Benzothiadiazole (BTZ-P6t, 5), 4,7-bis(5-{[m,p-bis(hexyloxy)phenyl]ethynyl}thien-2-yl)-2,1,3-Benzothiadiazole (TBTZ-P6t, 6), and 7,7′-({[m,p-bis(hexyloxy)phenyl]ethynyl}-2,1,3-benzothiadiazol-4,4′-ethynyl)-2,5-thiophene (BTZT-P6t, 7), and two arylvinylenes, 9,10-bis-{(E)-[m,p-bis(hexyloxy)phenyl]vinyl}-anthracene (A-P6d, 3), 9,10-bis-[(E)-(p-{(E)-[m,p-bis(hexyloxy)phenyl]vinyl}phenyl)vinyl]-anthracene (PA-P6d, 4). Trends in optical absorption spectra and electrochemical redox processes are first described. Next, the thin-film microstructures and morphologies of films deposited from solution under various conditions are investigated, and organic field-effect transistors (OFETs) and bulk heterojunction photovoltaic (OP...
M. Mobin - One of the best experts on this subject based on the ideXlab platform.
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Aryl-substituted unsymmetrical Benzothiadiazoles: synthesis, structure, and properties.
The Journal of organic chemistry, 2013Co-Authors: Rajneesh Misra, Prabhat Gautam, M. MobinAbstract:A family of unsymmetrical donor–acceptor, ferrocenyl-substituted Benzothiadiazoles of types D1–π–A−π–D2, D1–π–A1–π–A2, D1–A−π–D2, and D1–A1–A2–D2, bearing a variety of electron-donating and electron-withdrawing groups, were designed and synthesized. Their photophysical, electrochemical, and computational properties were explored, which show strong donor–acceptor interaction. The presence of electron-rich units anthracene (6f) and triphenylamine (6h), and an electron-deficient unit 1,1,4,4-tetracyanobuta-1,3-diene (TCBD) (9b) results in lowering of the band gap, which leads to a red shift of the absorption spectrum in these Benzothiadiazole systems. The single crystal structures of 6c, 6g, 7a, and 7b are reported, which show marvelous supramolecular interactions.
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Donor-acceptor ferrocenyl-substituted Benzothiadiazoles: synthesis, structure, and properties.
The Journal of organic chemistry, 2013Co-Authors: Rajneesh Misra, Prabhat Gautam, Thaksen Jadhav, M. MobinAbstract:This article reports the design, and synthesis of D−π1–A−π2–D unsymmetrical, and D−π1–A−π2–A−π1–D symmetrical type of ferrocenyl-substituted Benzothiadiazoles by the Pd-catalyzed Sonogashira, and Stille coupling reactions. The photophysical and electrochemical behavior of the ferrocenyl-substituted Benzothiadiazoles show strong donor–acceptor interaction. The increase in the number of acceptor Benzothiadiazole unit, results in the lowering of the energy gap, which leads to the bathochromic shift of the absorption spectrum. The single crystal X-ray structures of 3a, 5a, and 5g were obtained which show interesting supramolecular interactions.
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Donor–π–acceptor–π–donor ferrocenyl Benzothiadiazoles: synthesis, structure, and properties
Tetrahedron Letters, 2013Co-Authors: Rajneesh Misra, Prabhat Gautam, Rekha Sharma, M. MobinAbstract:Abstract A series of donor–π–acceptor–π–donor type of ferrocenyl substituted Benzothiadiazoles were designed, and synthesized by the Pd-catalyzed Sonogashira coupling reaction. The electrochemical, photophysical, thermal, and structural properties of ferrocenyl substituted Benzothiadiazoles are discussed. These properties show strong donor–acceptor interaction.
Fabio Silvestri - One of the best experts on this subject based on the ideXlab platform.
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Solution-Processable Low-Molecular Weight Extended Arylacetylenes: Versatile p-Type Semiconductors for Field-Effect Transistors and Bulk Heterojunction Solar Cells
Journal of the American Chemical Society, 2010Co-Authors: Fabio Silvestri, Assunta Marrocchi, Mirko Seri, Choongik Kim, Tobin J. Marks, Antonio Facchetti, A. TaticchiAbstract:We report the synthesis and characterization of a series of five extended arylacetylenes, 9,10-bis-{[m,p-bis(hexyloxy)phenyl]ethynyl}-anthracene (A-P6t, 1), 9,10-bis-[(p-{[m,p-bis(hexyloxy) phenyl]ethynyl}phenyl)ethynyl]-anthracene (PA-P6t, 2), 4,7-bis-{[m,p-bis(hexyloxy)phenyl]ethynyl}-2,1,3-Benzothiadiazole (BTZ-P6t, 5), 4,7-bis(5-{[m,p-bis(hexyloxy)phenyl]ethynyl}thien-2-yl)-2,1,3-Benzothiadiazole (TBTZ-P6t, 6), and 7,7'-({[m,p-bis(hexyloxy)phenyl]ethynyl}-2,1,3-benzothiadiazol-4,4'-ethynyl)-2,5-thiophene (BTZT-P6t, 7), and two arylvinylenes, 9,10-bis-{(E)-[m,p-bis(hexyloxy)phenyl]vinyl}-anthracene (A-P6d, 3), 9,10-bis-[(E)-(p-{(E)-[m,p-bis(hexyloxy)phenyl]vinyl}phenyl)vinyl]-anthracene (PA-P6d, 4). Trends in optical absorption spectra and electrochemical redox processes are first described. Next, the thin-film microstructures and morphologies of films deposited from solution under various conditions are investigated, and organic field-effect transistors (OFETs) and bulk heterojunction photovoltaic (OPV) cells fabricated. We find that substituting acetylenic for olefinic linkers on the molecular cores significantly enhances device performance. OFET measurements reveal that all seven of the semiconductors are FET-active and, depending on the backbone architecture, the arylacetylenes exhibit good p-type mobilities (mu up to approximately 0.1 cm(2) V(-1) s(-1)) when optimum film microstructural order is achieved. OPV cells using [6,6]-phenyl C(61)-butyric acid methyl ester (PCBM) as the electron acceptor exhibit power conversion efficiencies (PCEs) up to 1.3% under a simulated AM 1.5 solar irradiation of 100 mW/cm(2). These results demonstrate that arylacetylenes are promising hole-transport materials for p-channel OFETs and promising donors for organic solar cells applications. A direct correlation between OFET arylacetylene hole mobility and OPV performance is identified and analyzed.
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solution processable low molecular weight extended arylacetylenes versatile p type semiconductors for field effect transistors and bulk heterojunction solar cells
Journal of the American Chemical Society, 2010Co-Authors: Fabio Silvestri, Assunta Marrocchi, Mirko Seri, Choongik Kim, Tobin J. Marks, Antonio Facchetti, A. TaticchiAbstract:We report the synthesis and characterization of a series of five extended arylacetylenes, 9,10-bis-{[m,p-bis(hexyloxy)phenyl]ethynyl}-anthracene (A-P6t, 1), 9,10-bis-[(p-{[m,p-bis(hexyloxy) phenyl]ethynyl}phenyl)ethynyl]-anthracene (PA-P6t, 2), 4,7-bis-{[m,p-bis(hexyloxy)phenyl]ethynyl}-2,1,3-Benzothiadiazole (BTZ-P6t, 5), 4,7-bis(5-{[m,p-bis(hexyloxy)phenyl]ethynyl}thien-2-yl)-2,1,3-Benzothiadiazole (TBTZ-P6t, 6), and 7,7′-({[m,p-bis(hexyloxy)phenyl]ethynyl}-2,1,3-benzothiadiazol-4,4′-ethynyl)-2,5-thiophene (BTZT-P6t, 7), and two arylvinylenes, 9,10-bis-{(E)-[m,p-bis(hexyloxy)phenyl]vinyl}-anthracene (A-P6d, 3), 9,10-bis-[(E)-(p-{(E)-[m,p-bis(hexyloxy)phenyl]vinyl}phenyl)vinyl]-anthracene (PA-P6d, 4). Trends in optical absorption spectra and electrochemical redox processes are first described. Next, the thin-film microstructures and morphologies of films deposited from solution under various conditions are investigated, and organic field-effect transistors (OFETs) and bulk heterojunction photovoltaic (OP...
Narcis Avarvari - One of the best experts on this subject based on the ideXlab platform.
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Modulation of the charge transfer and photophysical properties in non-fused tetrathiafulvalene-Benzothiadiazole derivatives
Organic and Biomolecular Chemistry, 2015Co-Authors: Flavia Pop, Sabine Seifert, Jihane Hankache, Andreas Hauser, Narcis AvarvariAbstract:Bis(thiomethyl)- and bis(thiohexyl)-tetrathiafulvalene-bromo-Benzothiadiazoles, containing electron donor tetrathiafulvalene (TTF) and electron acceptor Benzothiadiazole (BTD) units, have been prepared by Stille coupling reactions between the TTF-SnMe3 precursors and BTD-Br2. In another series of experiments, TTF-acetylene-BTD compounds have been synthesized by Sonogashira coupling between either TTF-acetylenes and BTD-Br2 in low yields, or TTF-iodine and BTD-acetylene in moderate yields. In the compound TTF-C [[triple bond, length as m-dash]] C-BTD the TTF and BTD units are coplanar in the solid state, as shown by the single crystal X-ray structure, and there is segregation in the packing between the donor and acceptor units. All the derivatives have good electron donor properties, as determined by cyclic voltammetry measurements, and they can also be reversibly reduced thanks to the presence of the BTD moiety. UV-visible spectroscopy and photophysical investigations show the presence of an intramolecular charge transfer (ICT) band and an emission band originating from the charge transfer. Both the absorption and the emission are modulated by the substitution scheme and the insertion of the acetylenic bridge.
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Tetrathiafulvalene - Benzothiadiazoles as Redox-Tunable Donor - Acceptor Systems: Synthesis and Photophysical Study
Chemistry (Weinheim an der Bergstrasse Germany), 2013Co-Authors: Flavia Pop, Andreas Hauser, Narcis Avarvari, A. Amacher, Jie Ding, L. Daku, M. Koch, J. Hauser, Shi-xia Liu, Silvio DecurtinsAbstract:Electrochemical and photophysical analysis of new donor–acceptor systems 2 and 3, in which a Benzothiadiazole (BTD) unit is covalently linked to a tetrathiafulvalene (TTF) core, have verified that the lowest excited state can be ascribed to an intramolecular-charge-transfer (ICT) π(TTF)→π*(Benzothiadiazole) transition. Owing to better overlap of the HOMO and LUMO in the fused scaffold of compound 3, the intensity of the 1ICT band is substantially higher compared to that in compound 2. The corresponding CT fluorescence is also observed in both cases. The radical cation TTF+. is easily observed through chemical and electrochemical oxidation by performing steady-state absorption experiments. Interestingly, compound 2 is photo-oxidized under aerobic conditions.
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TetrathiafulvaleneBenzothiadiazoles as Redox-Tunable DonorAcceptor Systems: Synthesis and Photophysical Study
Chemistry - A European Journal, 2013Co-Authors: Flavia Pop, Andreas Hauser, Narcis Avarvari, A. Amacher, Jie Ding, L. Daku, M. Koch, J. Hauser, Shi-xia Liu, Silvio DecurtinsAbstract:Electrochemical and photophysical analysis of new donoracceptor systems 2 and 3, in which a Benzothiadiazole (BTD) unit is covalently linked to a tetrathiafulvalene (TTF) core, have verified that the lowest excited state can be ascribed to an intramolecular-charge-transfer (ICT) (TTF)(Benzothiadiazole) transition. Owing to better overlap of the HOMO and LUMO in the fused scaffold of compound 3, the intensity of the 1ICT band is substantially higher compared to that in compound 2. The corresponding CT fluorescence is also observed in both cases. The radical cation TTF+. is easily observed through chemical and electrochemical oxidation by performing steady-state absorption experiments. Interestingly, compound 2 is photo-oxidized under aerobic conditions.