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Visible-light-driven Photocatalytic N-arylation of Imidazole Derivatives and Arylboronic Acids on Cu/graphene catalyst.

ABSTRACT: N-aryl imidazoles play an important role as structural and functional units in many natural products and biologically active compounds. Herein, we report a photocatalytic route for the C-N cross-coupling reactions over a Cu/graphene catalyst, which can effectively catalyze N-arylation of imidazole and phenylboronic acid, and achieve a turnover frequency of 25.4 h(-1) at 25°C and the irradiation of visible light. The enhanced catalytic activity of the Cu/graphene under the light irradiation results from the localized surface plasmon resonance of copper nanoparticles. The Cu/graphene photocatalyst has a general applicability for photocatalytic C-N, C-O and C-S cross-coupling of arylboronic acids with imidazoles, phenols and thiophenols. This study provides a green photocatalytic route for the production of N-aryl imidazoles.

SUBMITTER: Cui YL

PROVIDER: S-EPMC4648406 | biostudies-other | 2015

REPOSITORIES: biostudies-other

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Project description:Creation of an innovative composite photocatalyst, to advance its performance, has attracted researchers to the field of photocatalysis. In this article, a new photocatalyst based on polyaniline/reduced graphene oxide (PANI/RGO) composites has been prepared via the in situ oxidative polymerization method employing RGO as a template. For thermoelectric applications, though a higher percentage (50 wt %) of RGO has been used, for photocatalytic activity, lesser percentages (2, 5, and 8 wt %) of RGO in the composite have given a significant outcome. Furthermore, photoluminescence (PL) spectra, time-resolved fluorescence spectra, and Brunauer-Emmett-Teller surface area analyses confirmed the improved photocatalytic mechanism. PANI/RGO composites under visible light irradiation exhibit amazingly improved activity toward the degradation of cationic and anionic dyes in comparison with pristine PANI or RGO. Here, a PANI/RGO composite, with 5 wt % RGO(PG2), has emerged as the best combination with the degradation percentages of 99.68, 99.35, and 98.73 for malachite green, rhodamine B, and congo red within 15, 30, and 40 min, respectively. Experimental findings show that the introduction of RGO can relieve the agglomeration of PANI nanoparticles and enhance the light absorption of the materials due to an increased surface area. Moreover, the PG2 composite also showed excellent photocatalytic activity to reduce noxious Cr(VI). The effective removal of Cr(VI) up to 94.7% at pH 2 was observed within only 15 min. With the help of the active species trapping experiment, a plausible mechanism for the photocatalytic degradation has been proposed. The heightened activity of the as-synthesized composite compared to that of neat PANI or RGO was generally because of high concentrations of •OH radicals and partly of •O2 - and holes (h+) as concluded from the nitroblue tetrazolium probe test and photoluminescence experiment. It is hoped that the exceptional photocatalytic performance of our work makes the conducting polymer-based composite an effective alternative in wastewater treatment for industrial applications.

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Visible-light-driven Photocatalytic N-arylation of Imidazole Derivatives and Arylboronic Acids on Cu/graphene catalyst.

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