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Synthesis, characterization, and investigation of catalytic activity of copper(II) porphyrin graphene oxide for azide–alkyne cycloaddition

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Abstract

A covalently cross-linked graphene oxide (GO) catalyst was prepared by a cross-linking process using nucleophilic reaction of copper(II)‐coordinated 5,10,15,20-tetrakis(aminophenyl)porphyrin (CuPPh) with carboxyl groups at the edges of GO (GO–CuPPh). The structure of the catalyst was characterized using different techniques such as Fourier-transform infrared (FT-IR) spectroscopy, scanning electron microscopy (SEM), transmission electron microscopy (TEM), energy-dispersive x-ray spectroscopy (EDS), thermogravimetric analysis (TGA), and inductively coupled plasma (ICP) spectroscopy. All analyses confirmed successful covalent immobilization of CuPPh on GO. The activity of the catalyst was then studied for synthesis of 1,4-disubstituted 1,2,3-triazoles derivatives by reaction of various aryl azides and different terminal alkynes in mild reaction condition with good to excellent yield.

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Acknowledgements

The authors are grateful to the Iran National Science Foundation and Ferdowsi University of Mashhad for financial support.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad, 91775‐1436, Iran

    Amir Khojastehnezhad, Mehdi Bakavoli & Mohammad Mehdi Khakzad Siuki

  2. Department of Chemistry, Mashhad Branch, Islamic Azad University, Mashhad, Iran

    Ali Javid

  3. Faculty of Chemistry and Chemical Engineering, Malek Ashtar University of Technology, Tehran, Iran

    Mansour Shahidzadeh

Authors
  1. Amir Khojastehnezhad
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  2. Mehdi Bakavoli
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  3. Ali Javid
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Correspondence to Amir Khojastehnezhad.

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Khojastehnezhad, A., Bakavoli, M., Javid, A. et al. Synthesis, characterization, and investigation of catalytic activity of copper(II) porphyrin graphene oxide for azide–alkyne cycloaddition. Res Chem Intermed 45, 4473–4485 (2019). https://doi.org/10.1007/s11164-019-03843-y

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