American Chemical Society
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Preparation of 6,13-Bis(trimethylsilyl)pentacene and Formation of Second-Ring Diels−Alder Adduct of Pentacene

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journal contribution
posted on 2011-01-07, 00:00 authored by Zhiying Jia, Shi Li, Kiyohiko Nakajima, Ken-ichiro Kanno, Tamotsu Takahashi
6,13-Bis(trimethylsilyl)pentacene was synthesized by a coupling reaction of bicyclic dilithiobutadiene with diiodonaphthalene followed by aromatization. Diels−Alder reaction of 6,13-bis(trimethylsilyl)pentacene with dienophiles afforded the corresponding second-ring adducts. Elimination of two silyl groups gave the second-ring Diels−Alder adducts of parent pentacene.