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Synfacts 2011(10): 1078-1078  
DOI: 10.1055/s-0030-1261157
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

Nine in a Row: Taming the Acenes

Contributor(s): Timothy M. Swager, Sébastien Rochat
B. Purushothaman, M. Bruzek, S. R. Parkin, A.-F. Miller, J. E. Anthony*
University of Kentucky, Lexington, USA
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Publication History

Publication Date:
20 September 2011 (online)

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Significance

Stabilization of higher acenes represents a notoriously challenging task. The synthesis developed here takes advantage of the concomitant beneficial effects of silylethyne substituents and electron-deficient phenyl groups. Further, fluorinated extremities are believed to enhance stability and π-stacking interactions. Products 1-3 are isolated as crystalline compounds, suitable for X-ray diffraction analysis. Moreover, solutions are stable enough to allow electrochemical and photophysical measurements to be performed.