Download PDF
Synfacts 2009(9): 0984-0984  
DOI: 10.1055/s-0029-1217676
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

Selective Dimerization of Indolocarbazoles

Contributor(s): Timothy M. Swager, Jason R. Cox
S. I. Wharton, J. B. Henry, H. McNab*, A. R. Mount*
The University of Edinburgh, UK
Further Information

Publication History

Publication Date:
21 August 2009 (online)

    Permissions and Reprints

Significance

The authors report the selective dimerization of indolo[3,2,1-jk]carbazole through an electrooxidative strategy. The synthesis begins with the flash vacuum pyrolysis of N-(2-nitrophenyl)carbazole to afford the indolocarbazole in 71% yield on a gram scale. Electrooxidation provides thin films of the three dimers (shown above) without forming any higher oligomers. The identity of the three dimers was determined through careful spectroscopic comparison of the components of the film with pure dimers synthesized through cross-coupling procedures.