二聚炔雌醇分子钳的合成及其对芳香胺分子的识别

SYNTHESIS AND RECOGNITION PROPERTIES OF MOLECULAR TWEEZERS FROM ETHYNYLESTRADIOL

合成 4个新的雌甾分子钳———二聚炔雌醇 ,其结构经IR ,1HNMR和MS表征 .利用分光光谱滴定法测定了它们与一系列芳胺客体形成的超分子配合物的稳定常数 ,对主 客体间尺寸大小匹配和识别作用推动力等进行了讨论 .将二聚炔雌醇与二聚雌二醇分子钳的识别性能进行了比较 ,结果表明前者的识别性能优于后者 ,其优良的识别性能可能主要来自于多重π πstacking作用。

Four new receptors (1～4) from ethynylestradiol have been synthesized. Their structures have been characterized by 1HNMR, IR and mass spectra. The association constants( K a ) and Gibbs free energy changes(- ΔG ) for the 1∶1 inclusion complexes of molecular tweezers 1～4 with aromatic amine have been examined by UV Visible spectroscopic titration in CHCl 3 at 25℃. The molecular recognition abilities of receptor for aromatic amine are discussed from the viewpoints of size fit relationship and interaction of the weak intermolecular forces. The recognition properties of two types of estrogen based molecular tweezers were compared. The results showed that the ability to complex aromatic amine of molecular tweezers from ethynylestradiol 1～4 is superior to that of molecular tweezers from estradiol 5～8. The excellent recognition ability may results from the multiple π π stacking interaction, hydrogen bonding and Van der Waals interaction.