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

作者：Cheng, Jian; Gao, Bingbing; Tang, Hao^*; Sun, Zhihong; Xu, Linxian; Wang, Lingyun; Cao, Derong^*

来源：Science China Chemistry, 2022, 65(3): 539-545.

DOI：10.1007/s11426-021-1186-2

• hexnut[12]arene
• nonporous adaptive crystals
• macrocycle
• macrocyclic arene
• pillararene
• iodine capture
• dye capture

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.