Journal
CHEM
Volume 2, Issue 1, Pages 125-138Publisher
CELL PRESS
DOI: 10.1016/j.chempr.2016.12.003
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Funding
- Marie Sklodowska-Curie Actions under the Seventh Framework Programme (FP7) through the Intra-European Marie Curie Fellowship MultiFun CP [328897]
- Freemasons Foundation of New Zealand through the Royal Society of New Zealand-Rutherford Foundation
- ERC FP7 Consolidator Grant Naturale CG [616417]
- Wellcome Trust Senior Investigator Award [098411/Z/12/Z]
- Wellcome Trust [098411/Z/12/Z] Funding Source: Wellcome Trust
- EPSRC [EP/J021199/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [1230949, EP/J021199/1] Funding Source: researchfish
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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.
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