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

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...

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Published in:Journal of the American Chemical Society 2018-10, Vol.140 (43), p.14357-14366
Main Authors: Hsieh, Ya-Chu, Wu, Cheng-Feng, Chen, Yi-Ting, Fang, Chia-Te, Wang, Chi-Shin, Li, Chia-Hsin, Chen, Liang-Yu, Cheng, Mu-Jeng, Chueh, Chu-Chen, Chou, Pi-Tai, Wu, Yao-Ting
Format: Article
Language:English
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.8b08840