Triazine New Cyclophane Synthesis And Application Of Intermediate Applications To Explore

In recent years, macrocyclic chemistry in the field of supramolecular chemistry has developed rapidly. In organic chemistry and supramolecular chemistry, the hottest studies are the design, synthesis and application of artificial organic compound which has molecular recognition properties. As the most representative host compound in host-guest chemistry, cyclophane have achieved remarkable achievement in many fields. In this thesis, we have synthesized three new classes of cyclophane compounds using cyanuric chloride and other relatively simple compounds under mild conditions. This dissertation divides into five chapters and the main contents and conclusions are listed as following:The chapter 1:Briefly introduce the basic concepts and the progress of crown ethers, cyclodextrins, calixarenes, cyclophanes, cucurbituril, prophyrin, phthalocyanine, cyclic peptide in the supramolecular chemistry. And we described the five approaches of the synthesis of cyclophanes and their application research.The chapter 2:Single-ring cyclophanes 1-5a, 1-5b,2-3a,2-3b,2-4,2-5a,2-6b are synthesized by using cyanuric chloride, p-nitrophenol, phenol, sodium methoxide, 4,4'-diaminodiphenyl methane and triethylamine, meanwhile they are characterized by Elemental analysis, IR, MALDI-TOF-MS and 1H-NMR. The results showed that:as the synthesis of cyclophanes 1-5a and 1-5b, the nitro reduction is a key procedure; in the synthesis of 2-3a,2-3b,2-4,2-5a,2-6b, the selection of the secondary acid agent is very important. In addition, all the procedures of cyclization should be operated under the highly diluted condition, otherwise it will produce polymer chain.The chapter 3:Using cyanuric chloride, o-phenylenediamine,4,4'-diaminodiphenyl methane and 1,6'-hexanediamine as raw materials, we have synthesized bicyclic cyclophanes 3-3 and 3-5. MALDI-TOF-MS showed the peak of the target substance, which really proved that the target compound have been synthesized, but because of the bicyclic cyclophane is very difficult to be dissolved, it can not be isolated and purified, leading to the result of elemental analysis dose not match the theoretical value. So, how to enhance the solubility of bicyclic cyclophane is important and difficult aspect of following work.The chapter 4:In view of the previously cyclophane relatively poor solubility characteristics, the focus of this section is to increase the solubility of cyclophane through the introduction of active groups to the cyclophane and successful in the synthesis of soluble cyclophane 4-3,4-5,4-6,4-7. At the same time, the perfect crystal of cyclophane 4-3 and 4-6 were gained, and their structures were characterized by the X-ray diffraction.The chapter 5:Some experiments were carried out to the synthetic compounds and their intermediates. Bacillus subtilis, Staphylococcus aureus, Escherichia coli were used for biological testing laboratories, found that the sterilization or inhibition effect of the intermediates were related with the number of chlorine atoms, with the reduction of the number of chlorine atoms, the bactericidal or bacteriostatic effect is gradually weakened. We also used the metal cations to carry out the recognition experiment for the synthetic soluble cyclophane 4-3 and 4-6, UV absorption spectra showed that the metal ions for different families, only some of the transition metal ions can be identified.