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.
Clément
Sébastien
S
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.
Meyer
Franck
F
De Winter
Julien
J
Coulembier
Olivier
O
Vande Velde
Christophe M L
CM
Zeller
Matthias
M
Gerbaux
Pascal
P
Balandier
Jean-Yves
JY
Sergeyev
Sergey
S
Lazzaroni
Roberto
R
Geerts
Yves
Y
Dubois
Philippe
P