Twisted Polycyclic Arenes from Tetranaphthyldiphenylbenzenes by Controlling the Scholl Reaction with Substituents
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AbstractHerein, we report two new types of twisted polycyclic arenes (2 a, b and 3 a, b) with constitutionally isomeric π-backbones, which are synthesized by controlling the Scholl reaction of 1,2,4,5-tetra(naphth-2-yl)-3,6-diphenylbenzene (1) with properly positioned electron-donating substituents. With a polycyclic backbone containing two [5]helicene and four [4]helicene moieties, 2 a and b are new members of multiple helicenes with interesting stereochemistries. The as-synthesized 2 a and b are the twisted isomers, and thermal isomerization of twisted-2 b results in anti-2 b, a more stable stereoisomer. Both twisted- and anti-2 b have been fully characterized, and the thermal isomerization of twisted-2 b has been studied with 1H NMR spectroscopy and DFT calculations. Compounds 3 a and b are new members of twistacenes, the benzannulated pentacene backbone of which exhibits an end-to-end twist as found from the crystal structure. Twisted- and anti-2 b are also found to function as p-type semiconductors in solution-processed thin film transistors, whereas the thin films of 3 b appear insulating presumably due to the lack of π–π interactions.
Acceptance Date06/10/2016
All Author(s) ListYong Yang, Luyan Yuan, Bowen Shan, Prof. Dr. Zhifeng Liu, Prof. Dr. Qian Miao
Journal nameChemistry - A European Journal
Volume Number22
Issue Number51
Pages18620 - 18627
LanguagesEnglish-United Kingdom
Keywordsarenes,organic semiconductors,oxidative cyclodehydrogenation,polycycles,regioselectivity
Web of Science Subject CategoriesChemistry, Multidisciplinary;Chemistry

Last updated on 2020-21-11 at 02:03