Angewandte Chemie. International edition in English 2015-06-01

One-step synthesis of [16]helicene.

Kazuyuki Mori, Takashi Murase, Makoto Fujita

Index: Angew. Chem. Int. Ed. Engl. 54 , 6847-51, (2015)

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Abstract

A single-strand arylene-vinylene precursor containing four phenylene and three naphthylene units linked together with six vinylene spacers undergoes helical folding via sextuple photocyclization to give a [16]helicene core in a single step. The phenylene and naphthylene units are arranged in the precursor such that unfavorable side reactions (anthracene or benzoperylene formation) are avoided, and this is the key to the success of the one-step synthesis of [16]helicene, which is the longest [n]helicene that has been synthesized to date. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.