Journal of the American Chemical Society 2012-06-27

6,12-Diarylindeno[1,2-b]fluorenes: syntheses, photophysics, and ambipolar OFETs.

Daniel T Chase, Aaron G Fix, Seok Ju Kang, Bradley D Rose, Christopher D Weber, Yu Zhong, Lev N Zakharov, Mark C Lonergan, Colin Nuckolls, Michael M Haley

Index: J. Am. Chem. Soc. 134(25) , 10349-10352, (2012)

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Abstract

Herein we report the synthesis and characterization of a series of 6,12-diarylindeno[1,2-b]fluorenes (IFs). Functionalization with electron donor and acceptor groups influences the ability of the IF scaffold to undergo two-electron oxidation and reduction to yield the corresponding 18- and 22-π-electron species, respectively. A single crystal of the pentafluorophenyl-substituted IF can serve as an active layer in an organic field-effect transistor (OFET). The important finding is that the single-crystal OFET yields an ambipolar device that is able to transport holes and electrons.