Studies On The Synthesis Of Calix[8]arenes And Their Molecular Recognition By Spectroscopic Methods

Calix[n]arenes with unique cavity structure is well known as 'The third generation supramolecule' followed crown ethers and cyclodextrins because it can recognize ionic and molecular guests via electrostatic, hydrogen-bonding, hydrophobic, π -π and inclusion interactions. Crown ethers and cyclodextrins stand for 'The first and second generation supramolecules', respectively. The great progress in the two generations hosts has been achieved in chemistry and supramolecular chemistry. However, in comparison with crown ethers and cyclodextrins, the structural advantage of calixarenes can't be exhibited because its poor solubility preludes the further studies in molecular recognition and practical application. Recently, the preparation of water-soluble calixarenes and their molecular recognition in the solutions providing good biologic compatibility become a challenge crossing research field in analytical chemistry and supramolecular chemistry. It has high academic value and promising application. In this thesis, the three water-soluble calix[8]arenes were synthesized and their molecular recognition were studied by sensitive and simple fluorimetric and ultraviolet spectroscopic methods. The main research contents are following as:1. The history, structural feature, synthetic methods and molecular recognition of calixarenes and so on were reviewed. Meanwhile, their applications in analytical chemistry were also summarized. The developing prospect of calixarenes was expected. All that is used as start point for further study in this thesis.2. The three water-soluble calix[8]arenes were synthesized according to Mannich reactionand diazo-coupling reaction. The host molecules include p-(N,N-dimethylamino-methyl)-calix[8]arene(CX8), p-octa(4'-carboxyphenylazo)-calix[8]arene (CPAC) and p-octa(4'-amidosulfanilacylazophenyl)-calix[8]arenes(ASPC). The chemical structures were characterized by analytical means, such as elemental analysis, infrared spectrum, ~1HNMR and electric spray ionization mass spectrum. As we know, in general, the biological recognition and enzyme catalysis can occur in water solution. Therefore, the preparation of water-soluble hosts and their molecular recognition in solution were...