Synthesis, solid-state structure, and electrochemical properties of thienodipyrimidine-2,4,5,7-tetra(thi)ones

Wright, Anna I., Kariuki, Benson M. ORCID: https://orcid.org/0000-0002-8658-3897 and Wu, Yi-Lin ORCID: https://orcid.org/0000-0003-0253-1625 2023. Synthesis, solid-state structure, and electrochemical properties of thienodipyrimidine-2,4,5,7-tetra(thi)ones. ARKIVOC 2023 (2) , 202311998. 10.24820/ark.5550190.p011.998

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Abstract

Thienodipyrimidine-2,4,5,7-tetra(thi)ones were prepared by one-pot photocyclization from barbituric acid derivatives. The structures of these tricyclic molecules with multiple (thio)carbonyl groups were determined by NMR and single-crystal X-ray diffraction analysis, and the electrochemical properties were studied by cyclic voltammetry and DFT calculations. The solid-state structures of these molecules feature dipolar C=S (or C=O), chalcogen-bonding, and π-stacking interactions. The presence of two adjacent thiocarbonyl groups allows for a two-center three-electron (2c/3e) interaction upon oxidation, significantly lowering the oxidation potential.

Item Type:	Article
Date Type:	Published Online
Status:	Published
Schools:	Advanced Research Computing @ Cardiff (ARCCA) Chemistry
Publisher:	ARKAT USA
ISSN:	1551-7012
Funders:	EPSRC
Date of First Compliant Deposit:	23 August 2023
Date of Acceptance:	18 June 2023
Last Modified:	11 Jun 2024 15:28
URI:	https://orca.cardiff.ac.uk/id/eprint/162000

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