Photochemical Double 5-exo Cyclization of Alkenyl-Substituted Dithienylacetylenes: Efficient Synthesis of Diarylated Dithienofulvalenes

Dr. Aiko Fukazawa, Takashi Karasawa, Dr. Hongyu Zhang, Kazumitsu Minemura, Dr. Cristopher Camacho, Dr. Jian Wang, Prof. Dr. Stephan Irle, Prof. Dr. Shigehiro Yamaguchi
Angewandte Chemie International Edition
Article first published online: 13 AUG 2013
DOI: 10.1002/anie.201303738

Keywords: cyclization; pentafulvalene; photoreaction; π conjugation; redox properties

Smooth and selective: Upon photoirradiation, bis(3-alkenyl-2-thienyl)acetylenes smoothly and selectively undergo double 5-exo-dig cyclization to produce a series of thiophene-fused pentafulvalenes with various aryl substituents. In this fused π-conjugated skeleton, the fused thiophene rings and the aryl substituents significantly modulate the electronic structure of the pentafulvalene skeleton.

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