新型大环主体的设计与合成是超分子化学最重要的研究方向之一。目前，已知的大环多具有单一空腔，而具有可变深穴空腔的大环非常罕见。我们最近合成了一种新型萘基大环——管[4]芳烃。该大环具有四种构象，每一种构象都具有深穴空腔，表现出了优异的客体键合性质。这相当于将四个大环糅合在一起，形成了一个具有强大键合能力的主体。在本项目中，我们拟系统地探索管[n]芳烃（n=3, 4, 5, 6…）的通用高效合成方法，拟采用“一锅法”和“片段法”合成管[n]芳烃的各种同系物，获得水溶性、两亲性、单修饰与多修饰的管[n]芳烃。在此基础上，我们拟采用NMR、ITC、X-Ray单晶衍射、荧光光谱、紫外光谱、停流光谱等手段深入研究管[n]芳烃的构象多样性与键合动力学和热力学之间的构效关系。在此基础上，尝试构建基于管[n]芳烃的复杂组装体以及分子开关，并探索水溶性和两亲性管[n]芳烃的分子识别与组装行为。

Design and synthesis of novel macrocyclic hosts is one of the most important topics in supramolecular chemistry. Currently, the known macrocyclic hosts often possess only one cavity, and the ones with adaptive and deep cavities are very rare. Recently, we have synthesized a novel naphthalene-based macrocyclic host, and named it oxatub[4]arene. This macrocycle has four conformers, and each of them has a deep cavity, showing very good host-guest binding properties. The present project aims to systematically explore the general and high-efficient synthetic methods of oxatub[n]arene (n = 3, 4, 5, 6…), synthesize the various analogues of oxatub[n]arenes by using “one-pot” and “fragment-coupling approach”, and obtain water-soluble, amphiphilic, mono- and multi-functionalized oxatub[n]arenes. Then, we will harness NMR, ITC, X-ray crystallography, fluorescence spectroscopy, UV-vis spectroscopy, and stopped-flow spectroscopy to thoroughly study the structure-function relationship between the conformational diversity of oxatub[n]arenes and their thermodynamic and kinetic behaviors. On this basis, we will try to construct complex supramolecular architectures and molecular switches based on oxatub[n]arenes, and explore the molecular recognition and self-assembly behaviors of water-soluble and amphiphilic oxatub[n]arenes.