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A CTV Analogue: Arene-Persubstituted Cyclotrixylohydroquinoylene and Its Derivatives
Jianmin Jiao1, Baobao Sun1, Yihan Ding1
1Key Laboratory of Mesoscopic Chemistry of MOE, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China.
Abstract:
A crown-shaped cyclotriveratrylene (CTV) analogue with persubstituted arene units-namely, cyclotrixylohydroquinoylene (CTX)-was synthesized from tetrasubstituted o-xylohydroquinone. Importantly, a series of CTX derivatives were prepared by introducing second bridged methylene, phenylphosphine oxide, and dimethylsilyl at the middle rim, referred to as CTX[CH], CTX[P(O)Ph], and CTX[SiMe], respectively, with the completely locked crown conformation, leading to the formation of unique C3-symmetric Chinese censer-shaped pocket structures. In addition, the water-soluble CTX[CH] derivative (WCTX[CH]) was synthesized from CTX[CH] by simple oxidation reaction with the modification at the upper rim, and its host-guest interaction with methyl viologen in water was investigated.
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