Synthesis and Supramolecular Organization of Regioregular Polythiophene Block Oligomers

[en] 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 p-p 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.

Disciplines :

Chemistry
Physics

Author, co-author :

Clement, Sebastien

Meyer, Franck

De Winter, Julien ; Université de Mons > Faculté des Sciences > Synthèse et spectrométrie de masse organiques

Coulembier, Olivier ; Université de Mons > Faculté des Sciences > Matériaux Polymères et Composites

Vande Velde, Christophe M. L.

Zeller, Matthias

Gerbaux, Pascal ; Université de Mons > Faculté des Sciences > Synthèse et spectrométrie de masse organiques

Balandier, Jean-Yves

Sergeyev, Sergey

Lazzaroni, Roberto ; Université de Mons > Faculté des Sciences > Service de Chimie des matériaux nouveaux

Geerts, Yves

Dubois, Philippe ; Université de Mons > Faculté des Sciences > Matériaux Polymères et Composites

Language :

English

Title :

Synthesis and Supramolecular Organization of Regioregular Polythiophene Block Oligomers

Publication date :

05 March 2010

Journal title :

Journal of Organic Chemistry

ISSN :

0022-3263

Publisher :

American Chemical Society, United States - District of Columbia

Volume :

Issue :

Pages :

1561-1568

Peer reviewed :

Peer Reviewed verified by ORBi

Research unit :

S816 - Matériaux Polymères et Composites
S817 - Chimie des matériaux nouveaux
S836 - Synthèse et spectrométrie de masse organiques

Research institute :

R400 - Institut de Recherche en Science et Ingénierie des Matériaux

Commentary :

Publié en ligne le 10 février 2010

Available on ORBi UMONS :

since 10 July 2010

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