Research On C-O Cross-coupling Reactions Of An Aliphatic Diol With The Aryl Halides, And The Synthesis And Properties Of The Alicyclic Diamine And The Polyimides Structurally Modified By Alicyclic Natural Camphor

Recently, the cross-coupling reaction to get the C-X (N, O, S, P) compounds involved by a variety of copper complexes and alkali is increasingly becoming a hot topic in organic synthesis. cross-coupling reaction catalyzed by Transition metal is under mild conditions,which allows us to get efficient synthesis of a series aromatic compounds containing C-X key; compared to Pd and Ni, Cu is a low-cost and low-toxicity metal,which has a better selectivity,besides, ligand is simple, cross-coupling reaction catalyzed by copper salt attract more and more attention by the people.However, after a lot of literature research, we learned that the more people study the coupling between the C-O between the phenol and aromatic halogenated ydrocarbons, and most of the alcohols involved in the coupling between the C-O are the lower aliphatic alcohols, and coupling reaction of cycloaliphatic diols are rarely reported. This paper attempts to complete the C-O coupling reaction of cycloaliphatic diols and halogenated aromatic hydrocarbons.Aromatic polyimide,as a high-performance polymers, have excellent thermal stability.mechanical properties and dielectric properties, and thus get widespread attention.However, due to the rigidity of the molecular chain, crystal and electronic polarization, there is a strong force between the polyimide molecular chain, resulting that polyimide is insoluble due to the close packing of molecular chains, refractory and difficult to process, at the same time, they have the higher dielectric constant. In addition, the colors of aromatic polyimide are darker,which the light transmittance used in the display (such as liquid crystal display). Studies have shown that the introduction of flexible chains (such as alicyclic structure) in the polyimide main chain can weaken the intramolecular and intermolecular charge transfer(CT), which reduces the dielectric constant of polyimide and improves their light transmittance and solubility, there are broad application prospects in high temperature and low dielectric material, liquid crystal alignment layer and photoconductive, in recent years they has attracted wide attention. Specifically.the research in this thesis was mainly divided into three parts of work.:In the first part of this paper, Firstly halogenated benzene imide is synthsis by the reation of halogenated phthalic anhydride and methylamines,then starting from an1,4-cyclohexane dimethanol and halogenated benzene imide as raw materials,and CuBr as a catalyst in the absence of ligand,alkyl-aryl diether was synthesized. the influencing factors of the coupling reaction is Investigated,besides,the structure of the product is confirmed,fluorescent properties of which is studied.In the second part of this paper, natural camphor with two-ring[2,2,1]structure was oxidized to diacid, reduced to diol, followed by esterification, reduced to diamine again to produce a novel alicyclic chiral diamine monomer (BABMT) containing1,2.2-trimethyl-cyclopentyl strutcure, and the structure of the diamine was confirmed by IR and NMR spectra. The new diamine monomer showed good solubility in most common solvents and its chiral structure was characterized by the optical rotation determination and circular dichroism tests.In the third part, polyimide films derived from alicyclic diamine were synthesiz-ed by two-step polymerization of BABMT with BPDA and ODPA, respectively, and the performance of four different films was investigated systematically.