Unexpected side chain oxidation in a swivel cruciform oligothiophene.
Two swivel cruciform oligothiophenes are investigated for the occurrence of oxidative ring closure reactions. Surprisingly, instead of intramolecular cyclizations, a regioselective side chain oxidation of two of the four alpha-methylene groups next to the terminal thiophene rings is detected for one of the oligomers. Such side chain oxidations may be one unintended degradation pathway in oligothiophene-based organic semiconductors used as the active layer of organic field effect transistors (OFETs), organic light emitting diodes (OLEDs), and organic solar cells (OSCs).
Makromolekulare Chemie and Institut fur Polymertechnologie, Bergische Universitat Wuppertal, Gauss-Srasse 20, D-42097 Wuppertal, Germany.
Jan-Moritz
JM
Koenen
Askin
A
Bilge
Sybille
S
Allard
Ronald
R
Alle
Klaus
K
Meerholz
Ullrich
U
Scherf