Department of Chemistry, Life Sciences and Environmental Sustainability, University of Parma, Parco Area delle Scienze 17/A, 43124 Parma, Italy.
Molecules. 2018 Oct 17;23(10):2670. doi: 10.3390/molecules23102670.
Two synthetic protocols for the introduction of fluorine atoms into resorcinarene-based cavitands, at the lower and upper rim, respectively, are reported. Cavitand , bearing four fluorocarbon tails, and cavitand , which presents a fluorine atom on the position of a diester phosphonate phenyl substituent, were synthesized and their complexation abilities toward the model guest sarcosine methyl ester hydrochloride were evaluated via NMR titration experiments. The effect of complexation on the F NMR resonance of the probe is evident only in the case of cavitand , where the inset of the cation-dipole and H-bonding interactions between the P=O bridges and the guest is reflected in a sizable downfield shift of the fluorine probe.
报道了两种将氟原子分别引入基于间苯二酚的杯芳烃的下边缘和上边缘的合成方案。合成了具有四个氟碳尾的杯芳烃 和在二酯膦酸苯酯取代基的 位置带有一个氟原子的杯芳烃 ，并通过 NMR 滴定实验评估了它们对模型客体肌氨酸甲酯盐酸盐的络合能力。只有在杯芳烃 的情况下，络合作用对探针的 F NMR 共振才有明显影响，其中 P=O 桥与客体之间的阳离子-偶极和氢键相互作用反映在氟探针的大幅度场移上。
