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

Weikang Xiao, Zhiqun He (Lead Author), Sonia Remiro Buenamanana, Rebecca Turner, Min Xu, Xiao Yang, Xiping Jing, Andrew N. Cammidge (Lead Author)

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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
Original languageEnglish
Pages (from-to)3286–3289
Number of pages4
JournalOrganic Letters
Issue number13
Early online date19 Jun 2015
Publication statusPublished - 2015


  • Discotic liquid crystals
  • synthesis
  • pyrazine

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