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Synfacts 2009(8): 0857-0857  
DOI: 10.1055/s-0029-1217464
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

Azapentacenes

Contributor(s): Timothy M. Swager, Trisha L. Andrew
S. Miao, A. L. Appleton, N. Berger, S. Barlow, S. R. Marder, K. I. Hardcastle, U. H. F. Bunz*
Georgia Institute of Technology and Emory University, Atlanta, USA
Further Information

Publication History

Publication Date:
23 July 2009 (online)

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Significance

Tetraazapentacene (3) was synthesized from dione 1 in two steps using a synthetic route analogous to that used to synthesize TIPS-pentacene (shown above). Compound 3 is an air- and water-stable, organic-soluble material that is capable of undergoing two sequential, reversible one-electron reduction processes. Compound 3 is very weakly fluorescent.