Studies On The Synthesis Of Cucurbit[6]urils And Their Molecular Recognition By Spectroscopic Methods

Supramolecular interactions are intermolecular actions with molecular recognition ability, that is, Vander Waals force, electrostatic action, hydrogen-binding, dipole-dipole, charge transfer and hydrophobic action based on synergistic stereochemistry effect. Molecular recognition is the selective inclusion complexation between host and guest, in which some special functions can be realized. It is the base of biological recognition, such as enzyme catalysis, nucleic acid duplicate, antigen and antibody, drug and target molecule interaction. The molecular recognition prevails in life procedure from beginning to end. The study of molecular recognition became the common key project provided for both chemists and biochemists. Cucurbiturils, known as ' The fourth generation supramolecule' is a kind of neotype host. It has unique cavity structure and can recognize guests including metal ions and organic molecules via supramolecular interactions. It has great application potentiality in the molecular recognition, molecular catalysis, molecular self-assembly, pollution water treatment, mimic enzyme and drug pilot carrier. In this thesis, the molecular recognition mechanism of cucurbiturils was studied by fluorescent spectroscopic and UV-spectroscopic methods. The methods are sensitive, real-time and convenient to monitor the recognition procedure, which belongs to the across frontier research field of analytical chemistry and supramolecular chemistry. The research results possess high academic value and bright application prospects. The main contents are as follows:1. The structural feature, synthetic methods, molecular recognition of cucurbiturils and their applications were comprehensively reviewed and surmised. The visa of their applications in analytical chemistry was described. It was the theoretical base and start point of the thesis.2. Cucurbit[6]uril, perhydroxycucurbit[6]uril and four glycoluril derivatives were synthesized and identified by structural analytical means. The formation mechanism of cavities of cucurbiturils were discussed. It can be found that the synthetic processes undergo a nucleophilic addition and condensation reaction. The cyclization reaction was dependent on the steric hindrance of glycolurils, reaction activity of substituents, tensile force of cucurbituril and son on.