Center for Supramolecular Chemistry & Catalysis and Department of Chemistry, College of Science, Shanghai University, 99 Shang-Da Road, Shanghai 200444, China.
Skaggs Institute for Chemical Biology and Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA.
Molecules. 2021 Mar 30;26(7):1922. doi: 10.3390/molecules26071922.
A water-soluble deep cavitand bearing amides on the upper rim and trimethyl ammonium groups on the feet was synthesized. The open-ended cavity is stabilized by the intramolecular hydrogen bonds formed between the adjacent amides, and the introduction of trimethylammonium imparts to the cavitand good solubility in water. The cavitand exhibits high binding affinity and selectivity to hydrophilic molecules in water. With certain guests, such as cyclohexyl alcohols, amines and acids, the recognition involves the synergistic action of hydrogen bonding with hydrophobic effects. The binding phenomena are interpreted in terms of a fixed solvent cage presented by the host to the guest.
合成了一种水溶性的深穴状主体化合物，其在上缘带有酰胺基，在支脚带有三甲铵基团。开环空腔由相邻酰胺之间形成的分子内氢键稳定，而三甲铵的引入则使主体在水中具有良好的溶解性。该主体在水中对亲水分子表现出高的结合亲和力和选择性。对于某些客体，如环己醇、胺和酸，识别涉及氢键与疏水相互作用的协同作用。这些结合现象可以用主体为客体提供的固定溶剂笼来解释。
