5,14-Diaryldiindeno[2,1- f:1¡¬,2¡¬ -j]picene: A New Stable [7]Helicene with a Partial Biradical Character
Journal
Journal of the American Chemical Society
Date Issued
2018
Author(s)
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.
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.
SDGs
Type
journal article