jo902490m_si_001.cif (11.54 kB)

Synthesis and Supramolecular Organization of Regioregular Polythiophene Block Oligomers

Download (11.54 kB)
dataset
posted on 05.03.2010 by Sébastien Clément, Franck Meyer, Julien De Winter, Olivier Coulembier, Christophe M. L. Vande Velde, Matthias Zeller, Pascal Gerbaux, Jean-Yves Balandier, Sergey Sergeyev, Roberto Lazzaroni, Yves Geerts, Philippe Dubois
The self-assembly of functional polythiophenes was studied by a bottom-up approach “from molecule to polymer”. The synthesis and the X-ray structure of 2,5-dibromo-3-styryl and 3-2′,3′,4′,5′,6′-pentafluorostyryl-thiophenes revealed a supramolecular arrangement controlled by π−π interactions between the aromatic rings. A [2 + 2] photocyclization reaction in the solid state of (E)-1-2′,5′-dibromo-3′-thienyl-2-pentafluorophenylethene triggers the formation of a rare cycloadduct comprising thiophene rings. The X-ray analysis confirmed its rctt stereochemistry. The synthesis of P3HT-b-P3ST and P3HT-b-P3STF block oligomers was achieved by a GRIM method in good yields. An indirect proof of well-defined nanostructured organization was provided by the partial photocyclization of pendant styryl moieties under UV irradiation.

History

Exports