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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18 Citations (Scopus)

Abstract

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 an o-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 derivative 1ab), 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
JournalJournal of the American Chemical Society
DOIs
Publication statusAccepted/In press - 2018 Jan 1

All Science Journal Classification (ASJC) codes

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

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    Hsieh, Y. C., Wu, C. F., Chen, Y. T., Fang, C. T., Wang, C. S., Li, C. H., Chen, L. Y., Cheng, M-J., Chueh, C. C., Chou, P. T., & Wu, Y-T. (Accepted/In press). 5,14-Diaryldiindeno[2,1- f:1′,2′ -j]picene: A New Stable [7]Helicene with a Partial Biradical Character. Journal of the American Chemical Society. https://doi.org/10.1021/jacs.8b08840