Regiochemical effects of sulfur oxidation on the electronic and solid-state properties of planarized oligothiophenes containing thieno[3,2-b]thiophene units.
The effect of position and degree of sulfur oxidation on the fundamental properties of a series of planarized thieno[3,2-b]thiophene S,S-dioxides derivatives was studied. The optical data reveal a red shift in the longest wavelength of absorption relative to the nonoxidized analogues that is indicative of a reduced HOMO-LUMO gap. The position of oxidation rather than the extent of oxidation is the most critical factor in controlling electronic properties. Single-crystal analysis reveals that some of the oligothiophene S,S-dioxides studied present pi-pi interactions which are completely absent in the nonoxidized analogue.
San Miguel
Lidaris
L
Department of Chemistry and the Macromolecular Science and Engineering Program, University of Michigan, 930 North University, Ann Arbor, Michigan 48109-1055, USA.
Matzger
Adam J
AJ