Synthesis Of Quinolnol And Naphthol And Resorcinol Derivatives Containing Azo-or Imino-Group And Their LB Films Properties

In this dissertation, six compounds containing quinolinol and naphthol and resorcinol connected by azo- or imino- group have been synthesized. The coupling reaction between long chain diazonium salt of alkyloxy benzenamine and 8-hydroxyquinoline , 1-hydroxynaphthalene , resorcinol can obtain 8-hydroxy-5-[[(4′-octadecyloxy)phenyl]azo]quinoli-ne(C18AzoHq), 8-hydroxy-5-[[(4′-hexadecyloxy)phenyl]azo]quinoline(C16AzoHq), 1-hydroxy-4-[[(4′-octadecyloxy)phenyl]azo]naphthalene(C18AzoNp),1-hydroxy-4-[[(4-hexadecyloxy)phenyl]azo]naphthalene(C16AzoNp),4-[[(4-octadecyloxy)phenyl]azo]-1,3-benzenediol (C16AzoBdiol).The condensation reaction between 4-octdecyloxybenzenamine and 5-formyl-8-hydroxyquinoline produces 8-hydroxy-5-[[[(4′-octadecyloxy)phenyl]imino]methyl]qui-noline(C18ImiHq).The structure has been characterized by elemental analysis, IR, 1H-NMRAmong these compounds, C18AzoHq, C16AzoHq, C18ImiHq and C16AzoBdiol are new compounds.These compounds can form stable monolayers on different subphases interface and the monolayers can be deposited onto solid substrates to form stable LB films.The properties of C16AzoHq, C18AzoNp and C18ImiHq in solutions and LB films have been investigated. C16AzoHq and C18AzoNp show acidichromism in LB films. And the color change is reversible. It can be recovered by using NH3 gas. Studies on the complex reaction by UV-Vis absorption and FT-IR spectroscopy show that there exits in situ complex reaction between C16AzoHq , C18ImiHq and a series of metal ions. The complex formation between the LB monolayer of C16AzoHq and the metal ions in solution at the air/water interface can be obtained. Different metal ions have different effect on the film properties of C16AzoHq and C18ImiHq. Studies on the surface configuration of C18ImiHq monolayer on the mica surface show that microstructure varies with subphase of metal ions. It can be seen that bilayers form on the surface of subphase from the high curve. C18ImiHq in LB films has strong fluorescence character. But it weaken greatly after C18ImiHq combines with Cu2+ ion.