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Issue 45, 2020
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Sulphonic acid functionalized porphyrin anchored with a meso-substituted triazolium ionic liquid moiety: a heterogeneous photo-catalyst for metal/base free C–C cross-coupling and C–N/C–H activation using aryl chloride under visible light irradiation

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Abstract

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

Graphical abstract: Sulphonic acid functionalized porphyrin anchored with a meso-substituted triazolium ionic liquid moiety: a heterogeneous photo-catalyst for metal/base free C–C cross-coupling and C–N/C–H activation using aryl chloride under visible light irradiation

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Supplementary files

Article information


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

New J. Chem., 2020,44, 19690-19712
Article type
Paper

Sulphonic acid functionalized porphyrin anchored with a meso-substituted triazolium ionic liquid moiety: a heterogeneous photo-catalyst for metal/base free C–C cross-coupling and C–N/C–H activation using aryl chloride under visible light irradiation

K. Bhansali, S. Raut, S. Barange and P. Bhagat, New J. Chem., 2020, 44, 19690
DOI: 10.1039/D0NJ03637D

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