Title
Synthesis and supramolecular organization of regioregular polythiophene block oligomers Synthesis and supramolecular organization of regioregular polythiophene block oligomers
Author
Faculty/Department
Faculty of Sciences. Chemistry
Publication type
article
Publication
Washington, D.C. ,
Subject
Chemistry
Source (journal)
The journal of organic chemistry. - Washington, D.C.
Volume/pages
75(2010) :5 , p. 1561-1568
ISSN
0022-3263
ISI
000274841400023
Carrier
E
Target language
English (eng)
Full text (Publishers DOI)
Affiliation
University of Antwerp
Abstract
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-phentafluorophenylethene triggers the formation of a rare cycloadduct comparing thiophene rings. The X-ray analysis confirmed its re11 stereochemistry. The synthesis of P3HT-b-P3ST and P3HT-b-P3STF block oligomers was acheived by a GRIM method in good yields. An indirect proof of well-defined nanostruactured organization was provided by the partial photocyclization of pendant styryl moieties under UV irradiation.
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