Synthesis of diindolocarbazoles by Cadogan reaction: route to ladder oligo(p-aniline)s.
Synthesis of diindolocarbazoles by Cadogan reaction: route to ladder oligo(p-aniline)s.
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DOI：
10.1021/jo049419o
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发表时间：
2004-07
期刊：
影响因子：
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通讯作者：
J. Bouchard;Salem Wakim;M. Leclerc
中科院分区：
文献类型：
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作者：
J. Bouchard;Salem Wakim;M. Leclerc
Symmetric and nonsymmetric diindolocarbazoles were successfully synthesized for the first time by a Cadogan ring closure using N-alkyl-2,7-disubstituted carbazole precursors. Cyclization reaction on N-alkyl-2,7-di(2'-nitrophenyl) carbazole derivatives is not regioselective and produced a separable mixture of symmetric and nonsymmetric diindolocarbazoles. A carbazole derivative with methyl protective groups at the 1- and 8-positions was therefore used to obtain a symmetric ladder oligo(p-aniline) (compound 22). Optical and electrochemical properties of compound 22 indicate that its neutral semiconducting form is stable in air. This novel class of electroactive ladder oligomers should create new opportunities in micro- and nanoelectronics.
