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).
Koenen
Jan-Moritz
JM
Makromolekulare Chemie and Institut fur Polymertechnologie, Bergische Universitat Wuppertal, Gauss-Srasse 20, D-42097 Wuppertal, Germany.
Bilge
Askin
A
Allard
Sybille
S
Alle
Ronald
R
Meerholz
Klaus
K
Scherf
Ullrich
U