Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 16, Issue 43, Pages 8106-8114Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c8ob02150c
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Funding
- ANR program project MAGMA [ANR-16-CE29-0027-01]
- French National Research Agency (ANR) as part of the Investissements d'Avenir program (Labex NanoSaclay) [ANR-10-LABX-0035]
- Agence Nationale de la Recherche (ANR) [ANR-16-CE29-0027] Funding Source: Agence Nationale de la Recherche (ANR)
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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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