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Host-Guest Chemistry of a Tetracationic Cyclophane, Namely, Cyclobis (paraquat-p-phenylene)

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Handbook of Macrocyclic Supramolecular Assembly

Abstract

In the year of 1988, Sir Fraser Stoddart, the chemistry Nobel Laureate of 2016 for his contribution in the development of molecular machines, designed and developed a rectangle-shaped host molecule, namely, cyclobis(paraquat-p-phenylene) (CBPQT4+). This tetracationic cyclophane represents another milestone in the river of supramolecular chemistry, because (i) CBPQT4+ is relatively synthetically accessible and (ii) CBPQT4+ can recognize a variety of π-electron guests in both fully oxidized state and biscationic diradical state, driven by donor-acceptor and radical-pairing interactions, respectively. In this chapter, we are going to make a rough discussion of the following issues of CBPQT4+, including (i) the structural feature of CBPQT4+; (ii) its preparation including the template-directed synthesis; (iii) its binding behavior in its oxidative and radical states, namely, CBPQT4+ and CBPQT2(•+), respectively; (iv) mechanically interlocked molecules including rotaxanes and catenanes containing CBPQT4+ as a macrocyclic building block whose switchable features have been taken advantage of in the design of molecular switches and machines; and (v) the extended derivatives of CBPQT4+. Even although a few other groups also employed CBPQT4+ ring for self-assembly and molecular recognition, in this chapter, we mainly focus on the works of the group led by Stoddart, the inventor of this tetracationic cyclophane.

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  1. Department of Chemistry, Zhejiang University, Hangzhou, China

    Hao Li, Tianyu Jiao & Libo Shen

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  1. Hao Li
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  2. Tianyu Jiao
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  1. College of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin, China

    Yu Liu

  2. College of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin, China

    Yong Chen

  3. College of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin, China

    Heng-Yi Zhang

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Li, H., Jiao, T., Shen, L. (2020). Host-Guest Chemistry of a Tetracationic Cyclophane, Namely, Cyclobis (paraquat-p-phenylene). In: Liu, Y., Chen, Y., Zhang, HY. (eds) Handbook of Macrocyclic Supramolecular Assembly . Springer, Singapore. https://doi.org/10.1007/978-981-15-2686-2_4

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