ORGANIC
LETTERS
2008
Vol. 10, No. 6
1199-1202
Synthesis, Structures, and Properties of
Unsymmetrical Heteroacenes Containing
Both Pyrrole and Furan Rings
Keiko Kawaguchi, Koji Nakano,* and Kyoko Nozaki*
Department of Chemistry and Biotechnology, Graduate School of Engineering,
The UniVersity of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-8656, Japan
knakano@chembio.t.u-tokyo.ac.jp; nozaki@chembio.t.u-tokyo.ac.jp
Received January 11, 2008
ABSTRACT
Unsymmetrical heteroacenes, 11-phenylbenzofuro[3,2-b]carbazole (Ph
catalyzed double N-arylation of arylamines. They characteristically form antiparallel cofacial
their unsymmetrical structures. Their physical properties show their potential for application as active layers in organic field-effect transistors.
−BFC) and its alkoxylated derivatives, were readily synthesized by palladium-
π
-stacking arrangements, which may result from
The exploration of new organic semiconducting molecules
is a crucial topic in organic-based electronic devices such
as organic field-effect transistors (OFETs).1 Recently, in-
tensive research efforts in this field have led to the develop-
ment of a number of organic semiconductors with high
carrier mobilities comparable to those of amorphous silicon.2-12
Among them, pentacene has achieved both an exclusively
high hole mobility of ∼3 cm2‚V-1‚s-1 and a high on/off ratio
of 108.2 However, pentacene possesses the disadvantage of
undergoing air degradation and/or photooxidation, which
poses problems for its practical use in organic devices.
Recently, heteroacenes with heteroatoms in fused frame-
works, such as thiophene-based dinaphtho[2,3-b:2′,3′-f]-
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10.1021/ol703110g CCC: $40.75
© 2008 American Chemical Society
Published on Web 02/16/2008