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Calix[n]imidazolium as a new class of positively charged homo-calix compounds

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  • Young Chun

    (Center for Superfunctional Materials, Pohang University of Science and Technology)

  • N Jiten Singh

    (Center for Superfunctional Materials, Pohang University of Science and Technology
    Present address: Core Technology Laboratory, Samsung SDI Co., Ltd, Yongin 446-577, Korea)

  • In-Chul Hwang

    (Center for Superfunctional Materials, Pohang University of Science and Technology
    Present address:Center for Nanomaterials, Sogang University, Seoul 121-742, Korea (I.-C.H.))

  • Jung Woo Lee

    (Center for Superfunctional Materials, Pohang University of Science and Technology)

  • Seong Uk Yu

    (Center for Superfunctional Materials, Pohang University of Science and Technology)

  • Kwang S Kim

    (Center for Superfunctional Materials, Pohang University of Science and Technology)

Abstract

Macrocycles based on neutral calixarenes and calixpyrroles have been extensively explored for ion binding, molecular assembly and related applications. Given that only these two types of calix compounds and their analogs are available, the introduction of new forms of widely usable calix macrocycles is an outstanding challenge. Here we report the quadruply/quintuply charged imidazole-based homo-calix compounds, calix[4/5]imidazolium. The noncovalent (C-H)+/π+-anion interactions of the imidazolium rings with anions inside and outside the cone are the stabilizing factors for crystal packing, resulting in self-assembled arrays of cone-shaped calix-imidazolium molecules. Calix[4]imidazolium senses fluoride selectively even in aqueous solutions. Calix[5]imidazolium recognizes neutral fullerenes through π+–π interactions and makes them soluble in water, which could be useful in fullerene chemistry. Not only derivatization and ring expansion of calix[n]imidazolium, but also their utilization in ionic liquids, carbene chemistry and nanographite/graphene exfoliation could be exploited.

Suggested Citation

  • Young Chun & N Jiten Singh & In-Chul Hwang & Jung Woo Lee & Seong Uk Yu & Kwang S Kim, 2013. "Calix[n]imidazolium as a new class of positively charged homo-calix compounds," Nature Communications, Nature, vol. 4(1), pages 1-8, June.
    • Handle: RePEc:nat:natcom:v:4:y:2013:i:1:d:10.1038_ncomms2758
    DOI: 10.1038/ncomms2758
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    Cited by:

    1. Sha Bai & Lu-Wen Zhang & Zi-Hang Wei & Fang Wang & Qing-Wen Zhu & Ying-Feng Han, 2024. "Calix[2]azolium[2]benzimidazolone hosts for selective binding of neutral substrates in water," Nature Communications, Nature, vol. 15(1), pages 1-10, December.

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