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Sulphonic Acid Functionalized Porphyrin Anchored with mesoSubstituted Triazolium Ionic Liquid Moiety: Heterogeneous PhotoCatalyst for Metal/Base Free C-C Cross-Coupling and C-N/C-H activation using Aryl Chloride under visible light irradiations

Abstract

We report an easy process to synthesize sulphonic acid functionalized porphyrin, anchored with meso-substituted triazolium ionic liquid moiety (SAFPTILM) for metal/base free C-C cross-coupling and C-N/C-H activation using aryl chloride under visible light irradiations. The acid strength has been measured by Hammett indicator. The SAFPTILM photocatalyst comprising 18 π-conjugated electronic systems, with the chromophore substituents on the meso-position can provide rapid electronic conducting channels during photocatalysis by irradiation of visible light. It was found that the SAFPTILM is an efficient photocatalyst for the Heck, Sonogashira, Buchwald, Ullmann/Fittig coupling and C-H activation of phenols with different aryl chlorides in absence of base/noble metal, using 5 W LED (yellow) light at ambient conditions. The low band gap (1.55 eV) of SAFPTILM with conjugation assists photocatalytic reaction using inactivated aryl chlorides, by easy excitation of electrons and transfer to the conjugated benzimidazlium based phenylene di-imine support delaying the recombination of photoinduced electron–hole pairs.

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Supplementary files

Article information


Submitted
19 Jul 2020
Accepted
01 Oct 2020
First published
07 Oct 2020

New J. Chem., 2020, Accepted Manuscript
Article type
Paper

Sulphonic Acid Functionalized Porphyrin Anchored with mesoSubstituted Triazolium Ionic Liquid Moiety: Heterogeneous PhotoCatalyst for Metal/Base Free C-C Cross-Coupling and C-N/C-H activation using Aryl Chloride under visible light irradiations

P. R. Bhagat, K. J. Bhansali, S. U. Raut and S. H. Barange, New J. Chem., 2020, Accepted Manuscript , DOI: 10.1039/D0NJ03637D

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