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Synthesis and Suzuki–Miyaura cross coupling reactions for post-synthetic modification of a tetrabromo-anthracenyl porphyrin

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Abstract

The outstanding properties of porphyrins and the extreme versatility of their synthesis and their functionalisation constitute real assets for the fabrication of opto- and electroactive materials or for biological applications. In the large collection of porphyrinic structures, meso-substituted anthracenylporphyrins are among the less studied. Here, we synthesised the 5,10,15,20-tetra-bromoanthracenylporphyrin (BrTAP) and we investigated its chemical reactivity by post-synthetic modification using Suzuki–Miyaura cross coupling reactions with a series of boronic acids to generate a collection of original tetra-anthracenyl porphyrin based molecules: tetraphenylanthracenylporphyrin (TPAP), tetratolylanthracenylporphyrin (TTAP), tetramethoxyphenylanthracenylporphyrin (TMPAP), tetranaphthylanthracenylporphyrin (TNAP) and tetrapyrenylanthracenylporphyrin (TPyAP). Optical characterisations of these modified porphyrins showed, in most cases, only emission of the porphyrin in the visible region with extinction of the fluorescence of PAHs in the UV or visible region.

Graphical abstract: Synthesis and Suzuki–Miyaura cross coupling reactions for post-synthetic modification of a tetrabromo-anthracenyl porphyrin

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Publication details

The article was received on 31 Aug 2018, accepted on 09 Oct 2018 and first published on 09 Oct 2018


Article type: Paper
DOI: 10.1039/C8OB02150C
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Synthesis and Suzuki–Miyaura cross coupling reactions for post-synthetic modification of a tetrabromo-anthracenyl porphyrin

    J. Pijeat, Y. J. Dappe, P. Thuéry and S. Campidelli, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB02150C

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