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Molecules 2015, 20(12), 21787-21801;

Significant Improvement of Optoelectronic and Photovoltaic Properties by Incorporating Thiophene in a Solution-Processable D–A–D Modular Chromophore

School of Applied Sciences, The Royal Melbourne Institute of Technology (RMIT) University, GPO Box 2476, Melbourne Victoria 3001, Australia
Medicinal Chemistry, Monash Institute of Pharmaceutical Sciences, Monash University, Parkville Victoria 3052, Australia
Virtual Nanoscience Lab, Commonwealth Scientific and Industrial Research Organization (CSIRO) Manufacturing, Parkville Victoria 3052, Australia
School of Chemistry, Physics and Mechanical Engineering, Queensland University of Technology (QUT), GPO Box 2434, Brisbane QLD 4001, Australia
Authors to whom correspondence should be addressed.
Academic Editor: Sergei Manzhos
Received: 6 October 2015 / Revised: 24 November 2015 / Accepted: 25 November 2015 / Published: 4 December 2015
(This article belongs to the Special Issue Molecular Engineering for Electrochemical Power Sources)
Full-Text   |   PDF [2574 KB, uploaded 4 December 2015]   |  


Through the incorporation of a thiophene functionality, a novel solution-processable small organic chromophore was designed, synthesized and characterized for application in bulk-heterojunction solar cells. The new chromophore, (2Z,2′Z)-2,2′-(1,4-phenylene)bis(3-(5-(4-(diphenylamino)phenyl)thiophen-2-yl)acrylonitrile) (coded as AS2), was based on a donor–acceptor–donor (D–A–D) module where a simple triphenylamine unit served as an electron donor, 1,4-phenylenediacetonitrile as an electron acceptor, and a thiophene ring as the π-bridge embedded between the donor and acceptor functionalities. AS2 was isolated as brick-red, needle-shaped crystals, and was fully characterized by 1H- and 13C-NMR, IR, mass spectrometry and single crystal X-ray diffraction. The optoelectronic and photovoltaic properties of AS2 were compared with those of a structural analogue, (2Z,2′Z)-2,2′-(1,4-phenylene)bis(3-(4-(diphenylamino)phenyl)-acrylonitrile) (AS1). Benefiting from the covalent thiophene bridges, compared to AS1 thin solid film, the AS2 film showed: (1) an enhancement of light-harvesting ability by 20%; (2) an increase in wavelength of the longest wavelength absorption maximum (497 nm vs. 470 nm) and (3) a narrower optical band-gap (1.93 eV vs. 2.17 eV). Studies on the photovoltaic properties revealed that the best AS2-[6,6]-phenyl-C61-butyric acid methyl ester (PC61BM)-based device showed an impressive enhanced power conversion efficiency of 4.10%, an approx. 3-fold increase with respect to the efficiency of the best AS1-based device (1.23%). These results clearly indicated that embodiment of thiophene functionality extended the molecular conjugation, thus enhancing the light-harvesting ability and short-circuit current density, while further improving the bulk-heterojunction device performance. To our knowledge, AS2 is the first example in the literature where a thiophene unit has been used in conjunction with a 1,4-phenylenediacetonitrile accepting functionality to extend the π-conjugation in a given D–A–D motif for bulk-heterojunction solar cell applications. View Full-Text
Keywords: solution-processable; bulk-heterojunction devices; donor–acceptor–donor; triphenylamine; thiophene; 1,4-phenylenediacetonitrile solution-processable; bulk-heterojunction devices; donor–acceptor–donor; triphenylamine; thiophene; 1,4-phenylenediacetonitrile

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Raynor, A.M.; Gupta, A.; Plummer, C.M.; Jackson, S.L.; Bilic, A.; Patil, H.; Sonar, P.; Bhosale, S.V. Significant Improvement of Optoelectronic and Photovoltaic Properties by Incorporating Thiophene in a Solution-Processable D–A–D Modular Chromophore. Molecules 2015, 20, 21787-21801.

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