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Synthesis of hetero-bifunctional, end-capped oligo-EDOT derivatives

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Title: Synthesis of hetero-bifunctional, end-capped oligo-EDOT derivatives
Authors: Spicer, C
Booth, M
Mawad, D
Armgarth, A
Nielsen, C
Stevens, MM
Item Type: Journal Article
Abstract: Conjugated oligomers of 3,4-ethylenedioxythiophene (EDOT) are attractive materials for tissue engineering applications, and as model systems for studying the properties of the widely used polymer PEDOT. We report here the facile synthesis of a series of keto-acid end-capped oligo-EDOT derivatives (n = 2-7) through a combination of a glyoxylation end capping strategy and iterative direct arylation chain extension. Importantly, these structures not only represent the longest oligo-EDOTs reported, but are also bench stable in contrast to previous reports on such oligomers. The constructs reported here can undergo subsequent derivatization for integration into higher order architectures, such as those required for tissue engineering applications. The synthesis of hetero-bifunctional constructs, as well as those containing mixed monomer units is also reported, allowing further complexity to be installed in a controlled manner. Finally, we describe the optical and electrochemical properties of these oligomers and demonstrate the importance of the keto-acid in determining their characteristics.
Issue Date: 12-Jan-2017
Date of Acceptance: 9-Dec-2016
URI: http://hdl.handle.net/10044/1/42939
DOI: https://dx.doi.org/10.1016/j.chempr.2016.12.003
ISSN: 2451-9294
Publisher: Elsevier: Cell Press
Start Page: 125
End Page: 138
Journal / Book Title: Chem
Volume: 2
Issue: 1
Copyright Statement: © 2017 The Author(s). Published by Elsevier Inc. This is an open access article under the CC BY license (http://creativecommons.org/licenses/by/4.0/).
Sponsor/Funder: Commission of the European Communities
British Heart Foundation
Wellcome Trust
Commission of the European Communities
Funder's Grant Number: PIIF-GA-2012-328897
RM/13/1/30157
098411/Z/12/Z
ERC-2013-CoG-616417
Keywords: C-H activation
SDG3: Good health and well-being
SDG7: Affordable and clean energy
conjugated polymer
end capping
oligomer
synthesis
thiophene
Publication Status: Published
Appears in Collections:Faculty of Engineering
Materials
Bioengineering
Faculty of Natural Sciences



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