Synthesis and supramolecular organization of regioregular polythiophene block oligomers.
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 pi-pi 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.
Laboratory of Polymeric and Composite Materials, Center of Innovation and Research in Materials and Polymers (CIRMAP), University of Mons UMONS, Place du Parc 20, 7000 Mons, Belgium.
Sébastien
S
Clément
Franck
F
Meyer
Julien
J
De Winter
Olivier
O
Coulembier
Christophe M L
CM
Vande Velde
Matthias
M
Zeller
Pascal
P
Gerbaux
Jean-Yves
JY
Balandier
Sergey
S
Sergeyev
Roberto
R
Lazzaroni
Yves
Y
Geerts
Philippe
P
Dubois