A CTV Analogue: Arene-Persubstituted Cyclotrixylohydroquinoylene and Its Derivatives
journal contributionposted on 2020-10-28, 20:04 authored by Jianmin Jiao, Baobao Sun, Yihan Ding, Hao Zheng, Yue Zhao, Juli Jiang, Chen Lin, Leyong Wang
A crown-shaped cyclotriveratrylene (CTV) analogue with persubstituted arene unitsnamely, 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[CH2], CTX[P(O)Ph], and CTX[SiMe2], 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[CH2] derivative (WCTX[CH2]) was synthesized from CTX[CH2] by simple oxidation reaction with the modification at the upper rim, and its host–guest interaction with methyl viologen in water was investigated.