4.5 Article

Efficient two-step synthesis of face-to-face meso-substituted bis(corrole) dyads

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2008, Issue 7, Pages 1181-1186

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200700985

Keywords

macrocycles; corroles; synthetic methods

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The synthesis of face-to-face meso-substituted bis(corrole) systems was revisited. By using a new synthetic pathway, the reaction was generalized to any type of linker and the yield was considerably increased. The dyads were obtained in yields up to 20% from a dialdehyde linker and dipyrromethane in a one-step reaction. The best reaction conditions required a decreased amount of TFA catalyst (1.4 equiv.) and a large excess of dipyrromethane (up to 8 equiv). Under these conditions, four bis(corrole)s linked by 2,2 '-diphenyl ether, 9,9-dimethylxanthene, anthracene, and dibenzofuran spacers were synthesized.

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