Synthesis and Supramolecular Organization of Regioregular Polythiophene Block Oligomers

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• 作者：Sbastien Clment ; 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
• 刊名：Journal of Organic Chemistry
• 出版年：2010
• 出版时间：March 5, 2010
• 年：2010
• 卷：75
• 期：5
• 页码：1561-1568
• 全文大小：877K
• 年卷期：v.75,no.5(March 5, 2010)
• ISSN：1520-6904

文摘

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.