Spicer, Christopher D. orcid.org/0000-0001-8787-578X, Booth, Marsilea A., Mawad, Damia et al. (3 more authors) (2017) Synthesis of Hetero-bifunctional, End-Capped Oligo-EDOT Derivatives. Chem. pp. 125-138. ISSN 2451-9294
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 poly(3,4-ethylenedioxythiophene). 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.
Metadata
Item Type: | Article |
---|---|
Authors/Creators: |
|
Copyright, Publisher and Additional Information: | © 2016 The Author(s). Published by Elsevier Inc. |
Keywords: | C-H activation,conjugated polymer,end capping,oligomer,synthesis,thiophene |
Dates: |
|
Institution: | The University of York |
Academic Units: | The University of York > Faculty of Sciences (York) > Chemistry (York) |
Depositing User: | Pure (York) |
Date Deposited: | 07 Sep 2018 09:30 |
Last Modified: | 26 Nov 2024 00:39 |
Published Version: | https://doi.org/10.1016/j.chempr.2016.12.003 |
Status: | Published |
Refereed: | Yes |
Identification Number: | 10.1016/j.chempr.2016.12.003 |
Related URLs: | |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:135440 |
Download
Filename: 1_s2.0_S2451929416302686_main.pdf
Description: 1-s2.0-S2451929416302686-main
Licence: CC-BY 2.5