Synthesis, Structure And Spectroscopic Properties Of Aza-2,5-Pyrazinophanes

From the fifties in last centuries, cyclophane has been interested and researched by a lot of chemists, especially the pyridinophane with the bridge containing the N atom and pyrazinophane with the bridge containing the S atom. In the meantime, Pyrazinophane is a very superior ligand, it is widely used in coordination chemistry. In order to research the pyrazinophane with the bridge containing the N atom widely, we use 2,5-dimethylpyrazine, through chlorination reaction, cyclization reaction with tosylamide monosodium salt, and detosyl reaction under the condition of concentrated sulfuric acid to want to get the production of 2,11-diaza[3.3](2,5)pyrazi- nophanes (isomeride), but we get pyrazinophane 2,11-diaza[3.3](2,5)-(2,6)pyrazinop- hane, we also get the production of N,N’,N’’-tritosyl-2,11,20-triaza[3.3.3] (2,5)pyrazi- nophane, it is the precursor of 2,11,20-triaza[3.3.3](2,5)pyrazinophane, we also get the no-cyclization production and the other macrocyclic(n=3) pyrazinophane. We test these productions by 1H NMR、HPLC, IR, X-Ray and so on. In the meantime, we also research the spectroscopic properties (UV spectrum and fluorescence spectrum) of these new productions.By using the method of solvent vapourization, we get the single crystal of N,N’,N’’-tritosyl-2,11,20-triaza[3.3.3](2,5)pyrazinophane, we also get the single crystal of asymmetric pyrazinophane N,N’-ditosyl-2,11-diaza[3.3](2,5)-(2,6)pyrazino- phane, the reason will be explained in the part of result and discussion.The important role of this thesis is to enrich the research of pyrazinophane with the bridge containing the N atom, especially to fill the vacancy of research of aza-pyrazinophane, although in the process of research there was something arise and the outcome is not very ideal, it still plays a role in the vacancy of aza-pyrazinophane, in the future work, we will continue to research the synthesis, structure, spectroscopic property and coordinated compound’s property with metal of 2,11-diaza[3.3](2,5)pyr- azinophane and macrocylic pyrazinophane(n=4,5,6), it will offer a good beginning for aza-pyrazinophane’s deeply research and widely used.