A CTV Analogue: Arene-Persubstituted Cyclotrixylohydroquinoylene and Its Derivatives

A crown-shaped cyclotriveratrylene (<b>CTV</b>) analogue with persubstituted arene unitsnamely, cyclotrixylohydroquinoylene (<b>CTX</b>)was synthesized from tetrasubstituted <i>o</i>-xylohydroquinone. Importantly, a series of <b>CTX</b> derivatives were prepared by introducing second bridged methylene, phenylphosphine oxide, and dimethylsilyl at the middle rim, referred to as <b>CTX­[CH</b>_<b>2</b><b>]</b>, <b>CTX­[P­(O)­Ph]</b>, and <b>CTX­[SiMe</b>_<b>2</b><b>]</b>, 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 <b>CTX­[CH</b>_<b>2</b><b>]</b> derivative (<b>WCTX­[CH</b>_<b>2</b><b>]</b>) was synthesized from <b>CTX­[CH</b>_<b>2</b><b>]</b> by simple oxidation reaction with the modification at the upper rim, and its host–guest interaction with methyl viologen in water was investigated.