Hexnut[12]arene and its derivatives: Synthesis, host-guest properties, and application as nonporous adaptive crystals

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) x 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.

Automated summary

Hexnut[12]arene and its derivatives, a new class of sixfold macrocyclic arenes, were synthesized by a one-pot reaction at room temperature and easily functionalized. The water-soluble fluorescent hexnut[12]arene showed high binding affinity to benzyl viologen dichloride. The nonporous adaptive crystal of hexnut[12]arene was found to capture both inorganic molecules and trace amounts of large organic molecules from water.