自然界中，很多复杂而精细的生命活动都是在微观的空腔或笼状结构中完成的，微观空腔或笼状结构的功能在于创造了一个对外界选择性开放的微观环境，在物质和能量存储以及分子笼内发生的催化、复制和感应等方面发挥作用。基于具有特殊拓扑结构的大曲面芳香体系的分子笼至今鲜有报道。在本论文中，我们设计合成了一类基于五联吡啶碗烯的配体，通过其与金属离子的配位作用构筑分子笼，深入研究了该型分子笼的自组装机理及其对不同客体分子的识别行为。研究结果表明，带异丁氧基侧基的五联吡啶碗烯配体能够通过与银离子间的配位作用在有机溶剂中自组装形成分子笼。该分子笼对金刚烷及其三种衍生物具有较强的络合作用，进而形成分子胶囊。但是溶剂对对该主客体络合的强度具有较大的影响；客体分子的缓释可以通过改变分子胶囊的溶剂环境得以实现，缓释速率则可以通过改变环境温度进行控制。此外，我们还进行了构筑水溶性分子笼的简单探索，制备了一类带聚醚链侧基的五联吡啶碗烯配体。

Many complex and delicate life activities are performed in microscopic cavities or cages in natural world. The function of microscopic cavities or cages is to create a microscopic environment that is selectively open to the outside world. It plays a role in the storage of matter and energy, as well as the catalysis, replication, and induction that occur in molecular cages. Molecular cages containing large π-surface with special topology in structure have been rarely reported. In this thesis, we designed and synthesized a kind of 1,3,5,7,9-penta(2,2'-bipyridin-5-yl) corannulene-based ligand. Molecular cage is constructed by coordinating with Ag+, self-assembly mechanism and guest recognition behavior have been studied thoroughly. The result shows that the 1,3,5,7,9-penta(2,2'-bipyridin-5-yl) corannulene-based ligand with isobutyl oxygen can form into molecular cages by self-assembling in organic solvents when coordinated with silver ions. The molecular cage can further form into capsule through recognition of adamantane or its derivatives. But the solvents have a great influence on the intensity of the host-guest complexation, the release of guest can be realized by changing the solvent environment of the molecule capsules, and the slow release rate can be controlled by changing the temperature. Besides, we have tried on some exploration of water-soluble molecular cage and a kind of 1,3,5,7,9-penta(2,2'-bipyridin-5-yl) corannulene-based ligands with polyether chain were synthesized.