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Synfacts 2007(1): 0039-0039  
DOI: 10.1055/s-2006-955674
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Stacked Conjugated Oligothiophenes

Contributor(s): Timothy M. Swager, Julian M. W. Chan
K. M. Knoblock, C. J. Silvestri, D. M. Collard*
Georgia Institute of Technology, Atlanta, USA
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Publication History

Publication Date:
15 December 2006 (online)

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Significance

The known compound 1, a bis­thieno-fused bicyclo[4.4.1]undecanone, was tetrabrominated and then further elaborated using Stille coupling chemistry to give oligothiophenes. After ketalization with ethylene glycol, the chair-chair conformation was locked in, resulting in a series of face-to-face stacked oligothiophenes. This forced stacking was shown to dramatically affect the redox properties of the oligomers. In addition, UV-Vis-near IR and ESR spectroscopic studies were also done.