5,14-Diaryldiindeno[2,1-f:1′,2′-j]picene: A New Stable [7]Helicene with a Partial Biradical Character

Ya Chu Hsieh, Cheng Feng Wu, Yi Ting Chen, Chia Te Fang, Chi Shin Wang, Chia Hsin Li, Liang Yu Chen, Mu Jeng Cheng, Chu Chen Chueh, Pi Tai Chou, Yao Ting Wu

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66 Citations (Scopus)


5,14-Diaryldiindeno[2,1-f:1′,2′-j]picene (DDP,1), a thermally and chemically stable helical arene, can be prepared from 1,4-bis[2-(arylethynyl)phenyl]benzene in four synthetic steps. Its helical backbone, which incorporates ano-quinodimethane moiety, was verified by X-ray crystallography, and this structural feature results in a very high barrier to racemization (exceeding 50 kcal/mol). DDP possesses versatile and promising properties, including a small HOMO-LUMO energy gap (1.31 eV for the dimesityl-substituted derivative1ab), an electron spin resonance (ESR)-active character, a small triplet-singlet energy gap (4.75 kcal/mol), broad photoabsorption covering the ultraviolet, visible, and near-infrared (NIR) regions, two-photon absorption in the NIR range, and respectable ambipolar charge-transport behavior in a solution-processed organic field-effect transistor.

Original languageEnglish
Pages (from-to)14357-14366
Number of pages10
JournalJournal of the American Chemical Society
Issue number43
Publication statusPublished - 2018 Oct 31

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry


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