Regiochemical effects of sulfur oxidation on the electronic and solid-state properties of planarized oligothiophenes containing thieno[3,2-b]thiophene units

被引:32
作者
Miguel, Lidaris San
Matzger, Adam J. [1 ]
机构
[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA
关键词
D O I
10.1021/jo801619q
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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.
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收藏
页码:7882 / 7888
页数:7
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