具有三维内部空腔的笼状化合物在反应催化、化合物提纯、不稳定分子储存和药物输送等方面具有巨大的潜在应用价值。近年来，科学家们依据超分子配位自组装的原则，设计组装形成了不同的人工分子笼。然而，人工分子笼的特性和应用价值还没有得到充分理解和挖掘；同时，由于分子笼的性质极其依赖于其具体的结构，更多类型的分子笼也有待构筑。基于高度对称分子基元的自组装是一种高效、通用的合成手性分子笼的策略。在此方面，作为一种具有独特的C5v对称碗状结构、高反应活性、以及动态分子手性的化合物，碗烯是一种构筑人工分子笼的优秀基元，并有可能赋予相关分子笼许多现有分子笼所不具备的独特性质。然而，到目前为止，基于碗烯的人工分子笼很少得到报导，其相关性质（特别是其独特的应用价值）还没有得到研究。 本论文中，我们基于五吡啶碗烯基有机金属分子笼的构型多样性，利用分子笼在包络不同的客体分子后构型分布的差异，开展了分子笼在复杂分子体系识别方向上的应用研究。我们利用前期所构筑的五吡啶碗烯基配位分子笼，研究了其对一系列复杂客体分子体系的主客体识别效果。在自然状态下，该分子笼以四种立体异构体（两对对映体）快速平衡的形式存在，客体分子的包络改变了不同对映体之间的平衡，从而引起了这两对对映体的比例变化。我们发现影响其比例变化的主要因素并不是这两种构型的分子笼本身的大小和形状，而是客体分子在分子笼内发生旋转而导致的立体体积的不同，因此，可以将这两种构型分子笼的比例大小作为识别客体分子的一个关键特征参数。我们通过研究所构筑的分子笼对三种金刚烷二醇的立体异构体、1-氟金刚烷、1-金刚烷醇以及几种氘代溶剂体系的主客体识别作用，证明了这一鉴定方法是可行的。 此外，我们探索了大空腔碗烯基有机金属分子笼的构筑，设计合成了五联吡啶苯基取代的碗烯基配体。通过实验探索，初步猜测该配体可以通过自组装的方式与金属银和汞配位，构筑形成两种有机金属分子笼，对这两种分子笼成功构筑的证明及其识别能力等的研究还在进行中。

Cages with three-dimensional internal cavities have great potential applications in reaction catalysis, compound purification, unstable molecule storage and drug delivery. In recent years, scientists have designed and assembled different artificial molecular cages from the principle of supramolecular coordination self-assembly. However, the characteristics and application value of molecular cage have not been fully explored. At the same time, as the nature of molecular cage is extremely dependent on its specific structure, more types of molecular cages need to be constructed. Self-assembly method based on highly symmetric building blocks is an efficient and versatile strategy for synthesizing chiral molecular cages. In this regard, as a compound with unique C5v symmetrical, bowl-shaped structure, high reactivity, and dynamic molecular chirality, corannulene is an excellent primitive for constructing artificial molecular cages. And it may endow the related molecular cages with many unique properties that the existing molecular cages do not have. However, until now, the artificial molecular cages based on corannulene have rarely been reported, and their related properties (especially its unique application value) have not been extensively studied. In this paper, the application of the cage in the recognition of complex molecular systems was studied, utilizing the divergence in conformational distribution of molecular cage upon encapsulating different guest molecules. The recognition effect of the cages on a series of complex guest molecular systems was studied. At the native state, the cage exists in the form of four stereoisomers (two enantiomers) in rapid equilibrium. Encapsulation of the guest molecule changes the balance between the two pairs of enantiomers, thus causing the change of ratio. The rebalanced conformational distribution is dependent on the shape and volume of the guest revolution, and thus can be regarded as a key characteristic parameter for the guest molecule. This concept is proved by studying the recognition effect of the constructed molecular cage on three stereoisomers of adamantanediol, 1-fluoroadamantane, 1-adamantanol and several deuterium substituted solvent systems. In addition, we also designed and synthesized a pentapyridyl phenyl substituted ligand based on corannulene for constructing a larger molecular cage. It is preliminarily speculated that this ligand can coordinate with silver and mercury by self-assembly to construct two kinds of metal-organic cages. And the research on the proof of successful construction of these two kinds of molecular cages and their recognition ability is still in progress.