Stabilized Copper(I) Oxide Nanoparticles Catalyze Azide-Alkyne Click Reactions in Water

Authors

  • Zhenfang Zhang,

    1. Key Laboratory of Bioactive Materials, Ministry of Education, Nankai University, Tianjin 300071, People's Republic of China, Fax: (+86)-22-2349-8775; phone: (+86)-22-2350-2111
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  • Changming Dong,

    1. College of Pharmacy, Nankai University, Tianjin 300071, People's Republic of China, Fax: (+86)-22-2350-7760; phone: (+86)-22-2350-8090
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  • Cuihong Yang,

    1. Key Laboratory of Bioactive Materials, Ministry of Education, Nankai University, Tianjin 300071, People's Republic of China, Fax: (+86)-22-2349-8775; phone: (+86)-22-2350-2111
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  • Di Hu,

    1. College of Pharmacy, Nankai University, Tianjin 300071, People's Republic of China, Fax: (+86)-22-2350-7760; phone: (+86)-22-2350-8090
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  • Jing Long,

    1. College of Pharmacy, Nankai University, Tianjin 300071, People's Republic of China, Fax: (+86)-22-2350-7760; phone: (+86)-22-2350-8090
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  • Ling Wang,

    1. College of Pharmacy, Nankai University, Tianjin 300071, People's Republic of China, Fax: (+86)-22-2350-7760; phone: (+86)-22-2350-8090
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  • He Li,

    1. College of Pharmacy, Nankai University, Tianjin 300071, People's Republic of China, Fax: (+86)-22-2350-7760; phone: (+86)-22-2350-8090
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  • Yue Chen,

    1. College of Pharmacy, Nankai University, Tianjin 300071, People's Republic of China, Fax: (+86)-22-2350-7760; phone: (+86)-22-2350-8090
    2. The State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071, People's Republic of China
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  • Deling Kong

    1. Key Laboratory of Bioactive Materials, Ministry of Education, Nankai University, Tianjin 300071, People's Republic of China, Fax: (+86)-22-2349-8775; phone: (+86)-22-2350-2111
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Abstract

A novel form of polyvinylpyrrolidone (PVP) coated copper(I) oxide nanoparticle (Cu2O-NP) was prepared and used to catalyze azide-alkyne click reactions in water under aerobic conditions. The nanoparticles were well dispersed in aqueous solutions and have a size of 20±10 nm, as determined by transmission electron microscope (TEM). Inductively coupled plasma (ICP), X-ray powder diffraction (XRD), and X-ray photoelectron spectroscopy (XPS) analyses demonstrated that the main content of Cu2O-NP is copper(I). The cytotoxicity of it was evaluated by an in vitro 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay and its catalytic efficiency for azide-alkyne click reactions was studied in water and organic solvents at physiological temperatures. Our results indicate that Cu2O-NP is more efficient in catalytic reactions in water for both aliphatic and aromatic azides and alkynes and less toxic than the commonly used CuSO4/reductant catalyst systems.

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