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. ORCID: https://orcid.org/0000-0001-7912-4310 (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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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
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: 04 Jul 2023 09:16
URI: https://ueaeprints.uea.ac.uk/id/eprint/53812
DOI: 10.1021/acs.orglett.5b01444


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