Issue 9, 2002

Synthesis of vinylated 5,10,15,20-tetraphenylporphyrins via Heck-type coupling reaction and their photophysical properties

Abstract

The direct coupling reaction between substituted olefins and 5,10,15,20-tetrakis(4-bromophenyl)porphyrin, via a Heck-type reaction, constitutes a versatile method for the vinylation of 5,10,15,20-tetrakis(4-bromophenyl)porphyrin to yield new vinylated tetraphenylporphyrins quantitatively. Another strategy for the vinylporphyrin synthesis has been developed. A phosphapalladacycle has been used as catalyst for the coupling reaction between 4-bromoaryl aldehydes and olefins to yield vinyl aldehydes quantitatively. These aldehydes have been condensed with pyrrole, by the one-step nitrobenzene method, to give the corresponding vinylated tetraphenylporphyrins. Photophysical studies of these new porphyrins are also reported.

Graphical abstract: Synthesis of vinylated 5,10,15,20-tetraphenylporphyrins via Heck-type coupling reaction and their photophysical properties

Article information

Article type
Paper
Submitted
22 Apr 2002
Accepted
18 Jun 2002
First published
10 Jul 2002

J. Chem. Soc., Perkin Trans. 2, 2002, 1583-1588

Synthesis of vinylated 5,10,15,20-tetraphenylporphyrins via Heck-type coupling reaction and their photophysical properties

M. M. Pereira, G. Muller, J. I. Ordinas, M. E. Azenha and L. G. Arnaut, J. Chem. Soc., Perkin Trans. 2, 2002, 1583 DOI: 10.1039/B203910A

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