Synthesis And Characterization OfΠ-conjugated Aromatic Alkyne Macrocles Consisting Of Endo-Ethylamino Groups

Shape-persistent macrocycles (SPMs) with its unique structure, can maintain a certain shape in solution or in the solid phase. Their ability to control the spatial arrangement of functional groups, together with their aggregation behavior, make them promising building blocks for tailor-made nanoscale objects and materials. At present, most of internal macrocyclic molecules without modified group have been compound. In this paper, we have successfully synthesized new macrocyclic molecules with modified group. Through benzene, acetylene linking alternately, it is similar to the ’spindle’ structure. External SPMs include dodecyl allyl and dodecyl ester groups; internal SPMs include ethylamino group and ether linkages.The main results are as follows:In the first chapter, The effect of feed ratie、reaction time、 temperature and solvent on the yield about the bromination of4-diethyl (methyl) amino benzaldehyde usind NBS by single-factor experiment method were investigated.The product was characterized with the help of1H-NMR、13C-NMR、GC-MS、IR, the melting point of the solid product was determined as well. The results showed that methyl or ethyl was broken down during the reaction.In the second chapter, new macrocyclic molecules with modified group have been successfully synthesized. At first, we explored the synthesis of macrocyclic compounds la, but the penultimate step’s compounds2a in the reaction route had poor solubility. This created great difficulties in determining its characterization and the subsequent cyclization. We designed a new molecule. To increase the solubility, The aldehyde had been replaced by dodecyl allyl group. The ether chain connected benzene reference the half ring docking method and template method. Through reasonable experiments, Compound1b have been got and excellent solubility. Compound1b was prepared through substitution reaction, esterification reaction, Sonogashira coupling reaction and so on. In the third chapter, we investigated the property of compounds1b. Target macrocyclic molecules had amide group and π-electron conjugated system, so strong fluorescence properties. We examined the macrocyclic compounds lb interact with metal ions by fluorescence test and found out compound1b could combine with Cu2+, Hg2+. Hg2+can make compound lb fluorescence quenching, Cu2+can make its fluorescence largely weaken but not quenching. We also tested the macrocyclic compound1b by TGA It’s thermal degradation temperature corresponding5wt%of weightlessness is322℃.This explained the macrocyclic molecular had good stability.