Regiochemical effects of sulfur oxidation on the electronic and solid-state properties of planarized oligothiophenes containing thieno[3,2-b]thiophene units
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作者:
Miguel, Lidaris San
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机构:Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA
Miguel, Lidaris San
Matzger, Adam J.
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Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USAUniv Michigan, Dept Chem, Ann Arbor, MI 48109 USA
Matzger, Adam J.
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机构:
[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA
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.