New Triazine Cyclophane And Pyridine Cyclophane Synthesis Research

Supramolecular chemistry is a cross subject in chemistry, which is contact with material sciences and information sciences, life sciences. It is at the forefront of contemporary chemistry. In organic chemistry and supramolecular chemistry, the design, synthesis and application of artificial macrocyclic compound with novel shapes and geometries have been continued to be of interest. The basic feature of supramolecular chemistry comes into being the host-guest complex in the basis of molecular recognition. As the most representative objects of host compounds, crown ethers, cyclodextrins, calixarenes, cyclophanes have achieved remarkable results in the main body of basic research and many areas.As a sort of important macrocyclic compound, the properties of cyclophane have been researched by chemists extensively. It is a kind of circular compound connected by methylene bridged and aromatic ring. There is a hole in the molecule and in which the aromatic ring is placed sideway, so the molecule is hydrophobic. As an artificially simulated enzyme, cyclophane can capture different organic molecules to form host-guest inclusive complex according to the differences of the ring shape, size and electrostatic effect. Currently, one direction of cyclophane research areas is changing the ring skeleton of the cyclophane structure, including the use of certain heterocyclic compounds such as pyridine, imidazole, benzimidazole, triazine, thiophene instead of benzene ring and with hetero-atoms S, N, O instead of methylene-bridged to form heterocyclophanes. The introduction of heteroatom changed the structure and the bonding performance of the cyclophane, which can fit different substrate molecules.This thesis did research on the synthesis of triazine-based cyclophane and pyridinophane. In part 1, a brief introduction of supramolecular chemistry and cyclophane chemistry, the development of pyridinophane, midazolophane, indolophane, tetrathiafulvalene cyclophane, benzotriazolophane and triazine-based cyclophane have been provided as well as a presentation of actuality and the foreground of the cyclophane research; In part 2, synthetic methods and the characterizations of several novel triazine-based cyclophanes were presented. By a fragment coupling approach, a number of hetero atoms -bridged triazine-based cyclophanes have been synthesized through cheap raw materials, an unusually high yielding and efficiency in gentle condition; In part 3, the synthetic method of pyridinophane was reported, the isophthalic acid and isophthalyl chloride were synthesized taking m-xylene as the raw material. With isophthalyl chloride and the Na salt of acetoacetate ester, the isophthaloyl-di-acetic ester was synthesized, finally two novel pyridinophane were obtained by Hantzsch synthetic method.