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DOI: 10.1055/s-0032-1318484
Synthesis of Dibenzothiophene, Dibenzofuran and Carbazole Donor–Acceptor Chromophores
Publication History
Received: 04 February 2013
Accepted after revision: 27 February 2013
Publication Date:
14 March 2013 (online)
Abstract
We present efficient synthetic protocols for functionalizing dibenzothiophene, dibenzofuran, and carbazole with hydroxy and nitro or cyano groups. The synthesis of these donor–acceptor chromophores is based on a key Suzuki–Miyaura coupling using an appropriately substituted aromatic boronic acid. Subsequent intramolecular SNAr reaction allows formation of the dibenzothiophene and dibenzofuran scaffolds, while a carbon–hydrogen activation reaction is employed to afford the carbazole. A final demethylation step unmasks the phenol moiety of the tricyclic chromophores. The UV/Vis absorption properties of the phenol and phenolate forms of these chromophores are also studied.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
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