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

Joffrey Pijeat 1 Yannick Dappe 2 Pierre Thuéry 3 Stéphane Campidelli 1
1 LICSEN - Laboratoire Innovation en Chimie des Surfaces et NanoSciences
NIMBE UMR 3685 - Nanosciences et Innovation pour les Matériaux, la Biomédecine et l'Energie (ex SIS2M)
2 GMT - Groupe Modélisation et Théorie
SPEC - UMR3680 - Service de physique de l'état condensé, IRAMIS - Institut Rayonnement Matière de Saclay
3 LCMCE - Laboratoire de Chimie Moléculaire et de Catalyse pour l'Energie (ex LCCEF)
NIMBE UMR 3685 - Nanosciences et Innovation pour les Matériaux, la Biomédecine et l'Energie (ex SIS2M)
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.
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https://hal-cea.archives-ouvertes.fr/cea-01935418
Contributor : Dominique Girard <>
Submitted on : Monday, November 26, 2018 - 4:26:42 PM
Last modification on : Monday, February 10, 2020 - 6:14:05 PM

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Joffrey Pijeat, Yannick Dappe, Pierre Thuéry, Stéphane Campidelli. Synthesis and Suzuki–Miyaura cross coupling reactions for post-synthetic modification of a tetrabromo-anthracenyl porphyrin. Organic and Biomolecular Chemistry, Royal Society of Chemistry, 2018, 16 (43), pp.8106 - 8114. ⟨10.1039/C8OB02150C⟩. ⟨cea-01935418⟩

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