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

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-...

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Main Authors: Aaron M. Raynor, Akhil Gupta, Christopher M. Plummer, Sam L. Jackson, Ante Bilic, Hemlata Patil, Prashant Sonar, Sheshanath V. Bhosale
Format: Article
Language:English
Published: MDPI AG 2015-12-01
Series:Molecules
Subjects:
Online Access:http://www.mdpi.com/1420-3049/20/12/19798
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spelling doaj-9ed99e66edca4c598d961522e93c51602020-11-25T00:16:02ZengMDPI AGMolecules1420-30492015-12-012012217872180110.3390/molecules201219798molecules201219798Significant Improvement of Optoelectronic and Photovoltaic Properties by Incorporating Thiophene in a Solution-Processable D–A–D Modular ChromophoreAaron M. Raynor0Akhil Gupta1Christopher M. Plummer2Sam L. Jackson3Ante Bilic4Hemlata Patil5Prashant Sonar6Sheshanath V. Bhosale7School of Applied Sciences, The Royal Melbourne Institute of Technology (RMIT) University, GPO Box 2476, Melbourne Victoria 3001, AustraliaSchool of Applied Sciences, The Royal Melbourne Institute of Technology (RMIT) University, GPO Box 2476, Melbourne Victoria 3001, AustraliaSchool of Applied Sciences, The Royal Melbourne Institute of Technology (RMIT) University, GPO Box 2476, Melbourne Victoria 3001, AustraliaSchool of Applied Sciences, The Royal Melbourne Institute of Technology (RMIT) University, GPO Box 2476, Melbourne Victoria 3001, AustraliaVirtual Nanoscience Lab, Commonwealth Scientific and Industrial Research Organization (CSIRO) Manufacturing, Parkville Victoria 3052, AustraliaSchool of Applied Sciences, The Royal Melbourne Institute of Technology (RMIT) University, GPO Box 2476, Melbourne Victoria 3001, AustraliaSchool of Chemistry, Physics and Mechanical Engineering, Queensland University of Technology (QUT), GPO Box 2434, Brisbane QLD 4001, AustraliaSchool of Applied Sciences, The Royal Melbourne Institute of Technology (RMIT) University, GPO Box 2476, Melbourne Victoria 3001, AustraliaThrough 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.http://www.mdpi.com/1420-3049/20/12/19798solution-processablebulk-heterojunction devicesdonor–acceptor–donortriphenylaminethiophene1,4-phenylenediacetonitrile
collection DOAJ
language English
format Article
sources DOAJ
author Aaron M. Raynor
Akhil Gupta
Christopher M. Plummer
Sam L. Jackson
Ante Bilic
Hemlata Patil
Prashant Sonar
Sheshanath V. Bhosale
spellingShingle Aaron M. Raynor
Akhil Gupta
Christopher M. Plummer
Sam L. Jackson
Ante Bilic
Hemlata Patil
Prashant Sonar
Sheshanath V. Bhosale
Significant Improvement of Optoelectronic and Photovoltaic Properties by Incorporating Thiophene in a Solution-Processable D–A–D Modular Chromophore
Molecules
solution-processable
bulk-heterojunction devices
donor–acceptor–donor
triphenylamine
thiophene
1,4-phenylenediacetonitrile
author_facet Aaron M. Raynor
Akhil Gupta
Christopher M. Plummer
Sam L. Jackson
Ante Bilic
Hemlata Patil
Prashant Sonar
Sheshanath V. Bhosale
author_sort Aaron M. Raynor
title Significant Improvement of Optoelectronic and Photovoltaic Properties by Incorporating Thiophene in a Solution-Processable D–A–D Modular Chromophore
title_short Significant Improvement of Optoelectronic and Photovoltaic Properties by Incorporating Thiophene in a Solution-Processable D–A–D Modular Chromophore
title_full Significant Improvement of Optoelectronic and Photovoltaic Properties by Incorporating Thiophene in a Solution-Processable D–A–D Modular Chromophore
title_fullStr Significant Improvement of Optoelectronic and Photovoltaic Properties by Incorporating Thiophene in a Solution-Processable D–A–D Modular Chromophore
title_full_unstemmed Significant Improvement of Optoelectronic and Photovoltaic Properties by Incorporating Thiophene in a Solution-Processable D–A–D Modular Chromophore
title_sort significant improvement of optoelectronic and photovoltaic properties by incorporating thiophene in a solution-processable d–a–d modular chromophore
publisher MDPI AG
series Molecules
issn 1420-3049
publishDate 2015-12-01
description 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.
topic solution-processable
bulk-heterojunction devices
donor–acceptor–donor
triphenylamine
thiophene
1,4-phenylenediacetonitrile
url http://www.mdpi.com/1420-3049/20/12/19798
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