Preparation And Properties Of Quinoline-based Heterocyclic Azo Compounds And Their Functionlized Polyacetylene

Quinoline-based azo compounds are very well photoelectric materials because of their largeπ-conjugated system, good coordination ability with metal elements, excellent chelating ability to life elements. In this dissertation, six new small quinoline-based azo compounds and two polymers with quinoline-based azo side groups were designed, synthesized and characterized by FTIR, ¹H-NMR and elemental analysis. Their thermal properties, optical properties and anions recognition ability were also investigated. The main contents of this thesis include the following points:1. The development, physicochemical properties, synthetical method and their application of heterocyclic azo-compounds and their polymers were reviewed in detail.2. Six small molecular quinoline-based azo-compounds were designed and synthesized, and their structures were characterized by IR and ¹H NMR. The synthetical method of the intermediate, 2-methyl-6-nitrylquinoline was optimized: useing crotonaldehyde and p-Nitroaniline as raw materials, appropriate acetic acid and toluene as solvent. p-Nitroaniline first reacted with acetic acid and then with crotonaldehyde, which effectively controlled the reaction rate. Toluene was used as emulsifier to improve effectively the yeild to 93%.3. The UV-vis absorption and Fluorescence spectra of the six target compounds are investigated. The results shows that the compounds show good optical properties. At the same time, The recognition peoperties of 3 aniline-quinoline azo-compounds on Br^-, Cl^-, F^-, Hg^-, H₂PO₄^- in DMSO were investigated, too. The results exhibit that recognition effect of 2-methyl-[6-（N,N-dimethyl） azo-phenyl]-quinoline on F^- ions observed and the UV absorption peak significantly red-shifts with obvious color chang.4. Two new kinds of quinoline-based azo-type homopolymer with a terminal alkynyl functional group were designed and synthesized using [Rh（nbd）Cl]₂-Et₃N as catalyst, and their structure were characterized by GPC, FTIR, ¹H-NMR and TGA. The results show that the two polymers were both soluble in most common organic solvents, such as CHCl₃、THF、CH₂Cl₂, DMF、DMSO and showed enhanced thermal stability compared to polyacetylene with no substituted groups.