A π-extended donor-acceptor-donor triphenylene twin linked via a pyrazine-bridge

Xiao, Weikang, He, Zhiqun, Remiro Buenamanana, Sonia, Turner, Rebecca, Xu, Min, Yang, Xiao, Jing, Xiping and Cammidge, Andrew N. (2015) A π-extended donor-acceptor-donor triphenylene twin linked via a pyrazine-bridge. Organic Letters, 17 (13). 3286–3289. ISSN 1523-7060

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Abstract

Beta-amino triphenylenes can be accessed via palladium catalyzed amination of the corresponding triflate using benzophe-none imine. Transformation of amine 6 to benzoyl amide 18 is also straightforward and its wide mesophase range demon-strates that the new linkage supports columnar liquid crystal formation. Amine 6 also undergoes clean aerobic oxidation to give a new twinned structure linked through an electron-poor pyrazine ring. The new discotic liquid crystal motif contains donor and acceptor fragments, and is more oval in shape rather than disk-like. It forms a wide range columnar mesophase. Absorption spectra are strong and broad; emission is also broad and occurs with a Stokes shift of ca. 0.7 eV, indicative of charge-transfer character

Item Type:	Article
Uncontrolled Keywords:	discotic liquid crystals,synthesis,pyrazine
Faculty \ School:	Faculty of Science > School of Chemistry (former - to 2024) Faculty of Science
UEA Research Groups:	Faculty of Science > Research Groups > Synthetic Chemistry (former - to 2017) Faculty of Science > Research Groups > Chemistry of Materials and Catalysis Faculty of Science > Research Groups > Chemistry of Light and Energy
Depositing User:	Pure Connector
Date Deposited:	24 Jul 2015 23:05
Last Modified:	29 Oct 2025 15:30
URI:	https://ueaeprints.uea.ac.uk/id/eprint/53812
DOI:	10.1021/acs.orglett.5b01444

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