近年来，分子间的相互作用研究引起了人们的广泛兴趣。分子间发生相互作用后，能使分子的物理、化学和分子生物学性质发生变化。研究分子间的相互作用有助于了解自然界和生物体内的变化规律，具有重要的科学意义和研究价值。本文合成并表征了几种吡啶、大环Shiff碱及大环多胺有机小分子，并通过紫外可见光谱和荧光发射光谱考察了它们与表面活性剂胶束、中性小分子和血清白蛋白之间的相互作用，具体可分为以下四个部分：一、阐述了研究分子间相互作用的意义和方法，并总结了吡啶、大环Shiff碱及大环多胺配体在仿酶催化、分子识别、抗癌抑菌等生物和医药方面的应用价值。二、合成并表征了两种新的配体：N-甲基-N-（4-氧杂-辛烷基）-2-氨基吡啶和N-甲基-N-（4-氧杂-十六烷基）-2-氨基吡啶。利用紫外可见光谱和核磁共振光谱研究了这些配体与不同表面活性剂的相互作用。结果显示配体与表面活性剂发生作用并增溶于胶束内的不同位置。分别在pH=7.5，25℃的CTAB 和 Brij35 胶束以及40℃的Brij35和SDS胶束溶液中，研究了配体及其Zn (II)配合物对α-吡啶甲酸对硝基苯酚酯（PNPP）水解反应的催化作用。实验数据显示在相同的条件下，在CTAB中水解反应的表观速率常数小于在Brij35中的表观速率常数，而Brij35中水解反应的表观速率常数又小于SDS中的表观速率常数。三、合成了两种新型的大环Shiff碱和大环多胺化合物，并用红外光谱、核磁共振谱和质谱等多种方法表征了它们的结构。通过紫外分光光谱滴定法，研究了大环Shiff碱和大环多胺化合物与四种中性小分子——尿素、二苯甲酮、三乙胺和巴比妥之间的相互作用。实验结果表明，大环Shiff碱与四种中性小分子都能发生相互作用，而大环多胺只能识别尿素和二苯甲酮分子，主体与客体之间形成1：1的超分子配合物。四种中性小分子与大环化合物的结合常数各不相同，其中以二苯甲酮最高。并用Chem3D(MM2)程序作为辅助手段模拟了大环化合物及其超分子配合物的最低能量构象。四、应用荧光光谱法和紫外可见光谱法研究了生理条件下牛血清白蛋白(BSA)与大环Shiff碱结合作用的机制。计算了Stem-Volmer猝灭常数Ksv，BSA与大环Shiff碱的结合常数和结合位点数以及相应的热力学参数ΔH，ΔS和ΔG，并讨论了两者作用力的类型。结果表明，大环Shiff碱对BSA的荧光猝灭机理符合生成配合物的静态猝灭机制，大环Shiff碱和BSA形成了化学计量为1：1的配合物，它们之间的作用力主要是氢键和范德华力。

The study on interaction between molecules in recent years has aroused wide interest. The physical, chemical, biological and molecular biological information of molecules will change after interaction. Detection of the interaction between molecules could help people understand the law of changes in the nature and living organisms, which have important scientific significance and research value.Some pyridylamino and macrocyclic polyamine and macrocyclic Shiff base ligands were synthesized and characterized in this paper. The interactions with surfactant micelle, neutral molecule and protein of these ligands have been measured by UV-vis and fluorescence spectra. This article is divided into four parts:1. An elaborated analysis of significance and research methods of molecular interaction was introduced. And outlines application value of the pyridine amine, macrocyclic Shiff base and macrocyclic polyamine ligands in biomimetic enzyme, molecular recognition, antimicrobial, antitumor and other biological and medical aspects.2. Two kinds of ligands were synthesized: N- (2-butoxyethyl) -N- methylpyridin -2-amine (L2) and N-(2-(dodecyloxy) ethyl)-N-methylpyridin-2-amine (L3). The interaction of these ligands with different surfactant has been investigated by UV and 1H NMR spectrum. The results reveal that the ligands interact with surfactants and penetrate into the micelles. The catalytic hydrolysis of p-nitrophenyl picolinate (PNPP) by ligands and their complex of Zn (II) were studied kinetically in the buffer CTAB and Brij35 micellar solution at 25 °C and in the buffer of Sodium dodecyl sulfonate (SDS) and Brij35 micellar solution at 40 °C, with pH=7.5.The experiment data show that in the same condition, the kobsd of the complexes in CTAB is smaller than kobsd of the complexes in Brij35 and the kobsd of the complexes in Brij35 is smaller than kobsd of the complexes in SDS. The effect of the structure of the ligands on the hydrolytic reaction of PNPP has been discussed in detail.3. Newly macrocyclic polyamine and macrocyclic Shiff base were synthesized and their structures were characterized by FT-IR, NMR and MS.Interactions with four neutral molecules, which are urea, diphenyl ketone, triethylamine and barbital, of macrocyclic polyamine and macrocyclic Shiff base were studied by UV-visible spectrophoto-metric tritation. The results have been showed that macrocyclic Shiff base could interact with all of four neutral molecules, while macrocyclic polyamine could only recognize urea and diphenyl ketone. The host compounds form 1:1 suprarmolecular complexes with the guests. The association constants of different hosts and guests were different, and diphenyl ketone has the highest association constant with macrocyclic compounds.Chem3D(MM2) software was employed to elucidate the configuration of macrocyclic compounds and their suprarmolecular complexes with the lowest energy.4. The interaction between macrocyclic Shiff base and Bovine serum albumin (BSA) was investigated by fluorescence and UV-vis absorbance spectroscopy. The Stern-Volmer quenching constant Ksv, the binding constant of macrocyclic Shiff base and BSA, the number of binding sites n and corresponding thermodynamic parameters ΔH, ΔS and ΔG were calculated. And the type of interaction between Shiff base and BSA was discussed. The results showed that the fluorescence quenching of BSA by macrocyclic Shiff base is mainly a result of the formation of Shiff base-BSA complex and hydrogen and van der Waals play major role in the reaction. And macrocyclic Shiff base form 1:1 suprarmolecular complexes with BSA.