Systematic Tuning of 2,1,3-Benzothiadiazole Acceptor Strength by Monofunctionalization with Alkylamine, Thioalkyl, or Alkoxy Groups in Carbazole Donor-Acceptor Polymers

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Title: Systematic Tuning of 2,1,3-Benzothiadiazole Acceptor Strength by Monofunctionalization with Alkylamine, Thioalkyl, or Alkoxy Groups in Carbazole Donor-Acceptor Polymers
Author(s): Creamer, A
Casey, A
Marsh, AV
Shahid, M
Gao, M
Heeney, M
Item Type: Journal Article
Abstract: A simple route to the preparation of alkylamine, thioalkyl, and alkoxy monofunctionalized 4,7-di(thiophen-2-yl)-2,1,3-benzothiadiazole) based monomers is reported from a common fluorinated precursor. Copolymerization with a carbazole comonomer under Suzuki conditions yielded a series of analogous donor–acceptor copolymers in which the only difference was the nature of the heteroatom (N, O, or S) on the benzothiadiazole core. This was shown to have a significant impact on the wavelength and intensity of the intramolecular charge transfer (ICT) absorption peak due to a combination of electronic and steric factors. Substantial differences were also observed in the solar cell performance of blends with PC71BM, with the octylamino substituted polymer exhibiting significantly lower performance than the other two polymers. This polymer also exhibited a reversible change in the optical spectra upon exposure to acid, suggesting potential as a sensing material.
Publication Date: 23-Mar-2017
Date of Acceptance: 9-Mar-2017
URI: http://hdl.handle.net/10044/1/48212
DOI: https://dx.doi.org/10.1021/acs.macromol.7b00235
ISSN: 0024-9297
Publisher: American Chemical Society
Start Page: 2736
End Page: 2746
Journal / Book Title: MACROMOLECULES
Volume: 50
Issue: 7
Copyright Statement: © 2017 American Chemical Society. This document is the Accepted Manuscript version of a Published Work that appeared in final form in Macromolecules after peer review and technical editing by the publisher. To access the final edited and published work see: https://dx.doi.org/10.1021/acs.macromol.7b00235
Keywords: Science & Technology
Physical Sciences
Polymer Science
OPEN-CIRCUIT VOLTAGE
ORGANIC SOLAR-CELLS
POWER CONVERSION EFFICIENCY
CONJUGATED POLYMERS
BAND-GAP
PHOTOVOLTAIC PERFORMANCE
COPOLYMERS
RECOMBINATION
OLIGOMERS
EXCHANGE
Polymers
03 Chemical Sciences
09 Engineering
Publication Status: Published
Embargo Date: 2018-03-23
Appears in Collections:Chemistry
Faculty of Natural Sciences



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