Journals / Turkish Journal of Chemistry / 2015 / Cilt: 39 - Sayı: 6

Sonogashira reactions for the synthesis of polarized pentacene derivatives

Pages
1180–1189
DOI
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Abstract

Five dissymmetrically functionalized anthracene analogues (\textbf{3a}--\textbf{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).

Özet

Five dissymmetrically functionalized anthracene analogues (\textbf{3a}--\textbf{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