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J Am Chem Soc. 2010 Feb 3;132(4):1261-3. doi: 10.1021/ja9095472.

Design, synthesis, and characterization of a persistent nonacene derivative.

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1
Department of Chemistry and Materials Science Program, University of New Hampshire, Durham, New Hampshire 03824-3598, USA.

Abstract

A significant technical barrier (i.e., facile oxidative degradation) that has prevented the preparation of large acenes has now been breached. Using a combination of experimentally and theoretically derived substituent effects, the design, synthesis, isolation, and characterization of the first persistent nonacene derivative is described. The molecular design strategy includes placement of arylthio (or alkylthio) substituents on the terminal rings of the nonacene skeleton, effectively converting an open-shell singlet diradical into a closed-shell system. These powerful substituent effects appear to be suitable for the synthesis of other persistent, soluble, large acene derivatives required for advanced thin-film organic semiconductor applications.

PMID:
20055388
DOI:
10.1021/ja9095472
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