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).

DOI

10.3906/kim-1505-117

Keywords

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

First Page

1180

Last Page

1189

Recommended Citation

SCHWEIZER, STEPHANE; ERBLAND, GUILLAUME; BISSERET, PHILIPPE; LALEVEE, JACQUES; NOUEN, DIDIER LE; and BLANCHARD, NICOLAS (2015) "Sonogashira reactions for the synthesis of polarized pentacene derivatives," Turkish Journal of Chemistry: Vol. 39: No. 6, Article 4. https://doi.org/10.3906/kim-1505-117
Available at: https://journals.tubitak.gov.tr/chem/vol39/iss6/4