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Significant improvement of optoelectronic and photovoltaic properties by incorporating thiophene in a solution-processable D-A-D modular chromophore

Raynor, Aaron M., Gupta, Akhil, Plummer, Christopher M., Jackson, Sam L., Bilic, Ante, Patil, Hemlata, Sonar, Prashant and Bhosale, Sheshanath V. 2015, Significant improvement of optoelectronic and photovoltaic properties by incorporating thiophene in a solution-processable D-A-D modular chromophore, Molecules, vol. 20, no. 12, pp. 21787-21801, doi: 10.3390/molecules201219798.

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Title Significant improvement of optoelectronic and photovoltaic properties by incorporating thiophene in a solution-processable D-A-D modular chromophore
Author(s) Raynor, Aaron M.
Gupta, AkhilORCID iD for Gupta, Akhil orcid.org/0000-0002-1257-8104
Plummer, Christopher M.
Jackson, Sam L.
Bilic, Ante
Patil, Hemlata
Sonar, Prashant
Bhosale, Sheshanath V.
Journal name Molecules
Volume number 20
Issue number 12
Start page 21787
End page 21801
Total pages 15
Publisher MDPI
Place of publication Basel, Switzerland
Publication date 2015-12-04
ISSN 1420-3049
Keyword(s) 1,4-phenylenediacetonitrile
bulk-heterojunction devices
donor–acceptor–donor
solution-processable
thiophene
triphenylamine
Coloring Agents
Crystallography, X-Ray
Electrochemistry
Photochemical Processes
Solar Energy
Solutions
Thiophenes
Summary 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 (13)C-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.
Language eng
DOI 10.3390/molecules201219798
Field of Research 0305 Organic Chemistry
Socio Economic Objective 0 Not Applicable
Copyright notice ©2015, The Authors
Free to Read? Yes
Use Rights Creative Commons Attribution licence
Persistent URL http://hdl.handle.net/10536/DRO/DU:30097895

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Every reasonable effort has been made to ensure that permission has been obtained for items included in DRO. If you believe that your rights have been infringed by this repository, please contact drosupport@deakin.edu.au.