Sonogashira reactions for the synthesis of polarized pentacene derivatives

Authors: STEPHANE SCHWEIZER, GUILLAUME ERBLAND, PHILIPPE BISSERET, JACQUES LALEVEE, DIDIER LE NOUEN, NICOLAS BLANCHARD

Abstract: Five dissymmetrically functionalized anthracene analogues (3a-e) were synthesized from commercially available 9,10-dibromoanthracene through an efficient bromine-iodine exchange followed by two successive Sonogashira coupling reactions. The resulting TMS-anthracene analogues are interesting building blocks for the preparation of highly $\pi$-conjugated dissymmetric pentacene-based dyads, which could be used as active semiconducting layers for organic field-effect transistors (OFETs).

Keywords: Sonogashira reaction, anthracene, pentacene, organic field-effect transistors

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