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Photochemical synthesis of oligomeric amphiphiles from alkyl oxoacids in aqueous environments

Rapf, Rebecca J., Perkins, Russell J., Yang, Haishen, Miyake, Garret M., Carpenter, Barry K. and Vaida, Veronica 2017. Photochemical synthesis of oligomeric amphiphiles from alkyl oxoacids in aqueous environments. Journal of the American Chemical Society 139 (20) , pp. 6946-6959. 10.1021/jacs.7b01707

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Abstract

The aqueous phase photochemistry of a series of amphiphilic α-keto acids with differing linear alkyl chain lengths was investigated, demonstrating the ability of sunlight-initiated reactions to build molecular complexity under environmentally relevant conditions. We show that the photochemical reaction mechanisms for α-keto acids in aqueous solution are robust and generalizable across alkyl chain lengths. The organic radicals generated during photolysis are indiscriminate, leading to a large mixture of photoproducts that are observed using high-resolution electrospray ionization mass spectrometry, but these products are identifiable following literature photochemical mechanisms. The alkyl oxoacids under study here can undergo a Norrish Type II reaction to generate pyruvic acid, increasing the diversity of observed photoproducts. The major products of this photochemistry are covalently bonded dimers and trimers of the starting oxoacids, many of which are multi-tailed lipids. The properties of these oligomers are discussed, including their spontaneous self-assembly into aggregates.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Advanced Research Computing @ Cardiff (ARCCA)
Chemistry
Publisher: American Chemical Society
ISSN: 0002-7863
Date of First Compliant Deposit: 30 June 2017
Date of Acceptance: 8 May 2017
Last Modified: 15 Mar 2020 10:36
URI: http://orca-mwe.cf.ac.uk/id/eprint/101961

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