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Novel metal free porphyrinic photosensitizers supported on solvent-induced Amberlyst-15 nanoparticles with a porous structure

Abstract

In this study, a series of meso-tetraarylporphyrins (aryl = phenyl, 2-methylphenyl and 2-chlorophenyl), H2T(aryl)P immobilized on nanosized Amberlyst-15 (nanoAmb) through acid-base reaction were utilized as highly efficient (turnover number in the range of 4 × (8000 to 10000), for 4 successive reactions with the same catalyst), stable and reusable heterogeneous photocatalysts for the aerobic oxidation of olefins under green conditions. Interestingly, nanoAmb with an average diameter less than 200 nm was produced from Amb beads by overnight magnetic stirring in ethyl acetate at room temperature. The catalysts may be reused at least four times without significant decrease in the catalytic activity. The immobilization of porphyrin on the polymer was confirmed by diffuse reflectance UV-vis and IR spectroscopy. Also, the supported porphyrin was released from nanoAmb surface by alkaline treatment and analyzed by UV-vis spectroscopy. N2 porosimetry analysis showed significant decreased BET surface area and pore volume values of the polymer after the immobilization of porphyrins. The influence of different parameters including the photosensitizer to olefin molar ratio, porphyrin loading, solvent, type of light source and the meso substituents has been investigated. H2T(2-Me)PP@nanoAmb and H2T(2-Cl)PP@nanoAmb showed the highest oxidative stability and catalytic activity among the series of porphyrins, respectively. In order to overcome the photooxidative degradation of porphyrin photosensitizers, different degrees of catalyst loading were examined and that with the lowest loading showed the best performance. The use of 1,4-benzoquinone and 1,3-diphenylisobenzofuran as the quencher of superoxide anion radical and singlet oxygen species revealed that oxidation reaction mainly proceeds with a singlet oxygen mechanism.

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Publication details

The article was accepted on 05 May 2017 and first published on 05 May 2017


Article type: Paper
DOI: 10.1039/C7NJ00791D
Citation: New J. Chem., 2017, Accepted Manuscript
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    Novel metal free porphyrinic photosensitizers supported on solvent-induced Amberlyst-15 nanoparticles with a porous structure

    A. Heydari-turkmani, S. Zakavi and N. Nikfarjam, New J. Chem., 2017, Accepted Manuscript , DOI: 10.1039/C7NJ00791D

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