Hexnut12arene and its derivatives: Synthesis, host-guest properties, and application as nonporous adaptive crystals

摘要

Hexnut[12]arene(HN[12])and its derivatives,a new class of sixfold macrocyclic arenes,were designed and synthesized in reasonable yield by a one-pot reaction at room temperature using dimethoxymethane as a methylene source.HN[12],which bears a large,symmetric,and rigid cavity,was easily functionalized at both the methylene bridges and the hydroquinone units.A water-soluble fluorescent HN[12]was synthesized and used as a host to encapsulate benzyl viologen dichloride in water with a high binding affinity of(3.4±0.2)×10^(6)M^(-1).The nonporous adaptive crystal(NAC)of HN[12]was found to capture not only inorganic molecules(iodine)but also trace amounts of large organic molecules(basic fuchsine)from water,which greatly expands the scope of NACs for adsorption.