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Issue 12, 2017
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A thiourea-functionalized metal–organic macrocycle for the catalysis of Michael additions and prominent size-selective effect

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Abstract

A discrete tetranuclear thiourea-based metal–organic macrocycle (MOM) with a large size was constructed by a well-designed organic ligand and nickel(II) ions via self-assembly. Incorporating thiourea groups as hydrogen-bond donors into a metal–organic complex system leads to a new approach for synthesizing functionalized heterogeneous catalysts, as this not only introduces coordination sites serving as chelators, but also overcomes the issues of self-association via intermolecular H-bonding, often occurring in homogeneous systems. The packing structure of this material formed a confined environment suitable for the access of substrate molecules dragged by the strong hydrogen-bond interactions from the thiourea groups, thus achieving a high catalytic performance in Michael additions of nitrostyrenes to nitroalkanes, with remarkable yields and size-selectivity in heterogeneous phase. Moreover, a comparison of the IR spectrum of Ni–SPT with the spectra of dimethyl malonate- and β-nitrostyrene-impregnated Ni–SPT indicated that both substrate molecules, β-nitrostyrene and dimethyl malonate, were able to access the cavity of the trimeric subunit.

Graphical abstract: A thiourea-functionalized metal–organic macrocycle for the catalysis of Michael additions and prominent size-selective effect

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Publication details

The article was received on 12 Nov 2016, accepted on 14 Feb 2017 and first published on 22 Feb 2017


Article type: Paper
DOI: 10.1039/C6DT04299F
Citation: Dalton Trans., 2017,46, 4086-4092
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    A thiourea-functionalized metal–organic macrocycle for the catalysis of Michael additions and prominent size-selective effect

    L. Yang, L. Zhao, Z. Zhou, C. He, H. Sun and C. Duan, Dalton Trans., 2017, 46, 4086
    DOI: 10.1039/C6DT04299F

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