Conducting Polymers Containing peri -Xanthenoxanthenes via Oxidative Cyclization of Binaphthols

TitleConducting Polymers Containing peri -Xanthenoxanthenes via Oxidative Cyclization of Binaphthols
Publication TypeJournal Article
Year of Publication2009
AuthorsSong, C, Swager, TM
Date Publishedmar
Keywordsbinaphthol thiophene moiety polymer prepn oxidativ, xanthenoxanthene moiety conducting polymer prepn

We report an electrochem. transformation of binaphthols to give peri-xanthenoxanthene (PXX) groups in small mols. and within polymer backbones. The monomer 7,7'-bis(2,2'-bithiophen-5-yl)-1,1'-bi-2,2'-naphthol (2) was subjected to electropolymn., resulting in the segmented conducting polymer that is stable at low potentials. However, high-potential electrochem. oxidn. promoted cyclization of binaphthol units gives PXX, which transforms the moderately conducting segmented polymer into a highly conducting fully conjugated polymer. This oxidative cyclization is a highly effective means by which to incorporate a planar polycyclic heteroarom. structure (i.e., PXX) into thiophene-based conducting polymers. A model compd. study conclusively proved the proposed oxidative cyclization scheme. [on SciFinder(R)]