【作者】 刘海霞；

【导师】 杜洪光；

【作者基本信息】 北京化工大学 ， 应用化学， 2003， 硕士

【摘要】 本文合成了六种含有偶氮或亚胺基团的羟基喹啉、萘酚和间苯二酚的两亲性衍生物。长链烷氧基苯胺重氮化反应后,与8-羟基喹啉、1-萘酚、和间苯二酚进行偶合反应,得到了5-(4′-十八烷氧基苯偶氮基)-8-羟基喹啉(C18AzoHq)、5-(4′-十六烷氧基苯偶氮基)-8-羟基喹啉(C16AzoHq)、4-(4′-十八烷氧基苯偶氮基)-1-萘酚(C18AzoNp)、 4-(4′-十六烷氧基苯偶氮基)-1-萘酚(C16AzoNp)和4-(4′-十六烷氧基苯偶氮基)-1,3-苯二酚(C16AzoBdiol),十八烷氧基苯胺与8-羟基-5-喹啉甲醛进行缩合反应得到了5-(4′-十八烷氧基苯基亚胺甲基)-8-羟基喹啉(C18ImiHq),结构通过元素分析、核磁共振氢谱和红外光谱得到了表征。其中化合物C18AzoHq、C16AzoHq、C18ImiHq和C16AzoBdiol是新的化合物,未见文献报道。这些化合物可以在不同的亚相表面形成稳定的单分子膜,进而沉积在固体载体表面形成稳定的LB膜。本文研究了化合物C16AzoHq、C18AzoNp和C18ImiHq在溶液及LB膜中的性质:化合物C16AzoHq和C18AzoNp可发生LB膜中的酸致变色反应,该反应是可逆的,可用碱性物质NH3·H2O使其恢复;采用UV-Vis光谱和FT-IR光谱对化合物C16AzoHq和C18ImiHq与金属离子络合进行了研究,结果表明,它们可以和一系列金属离子发生原位络合,化合物C16AzoHq的单层LB膜还可以和溶液中的金属离子发生膜表面的络合;不同的金属离子,对C16AzoHq和C18ImiHq分子的成膜性能产生不同的影响;首次用原子力显微镜对C18ImiHq单分子膜在云母片(mica)表面上的分子膜形态进行了研究,结果发现当亚相金属离子不同时,LB膜表现出不同的微观结构,高度曲线表明C18ImiHq在金属离子的亚相上形成双层膜结构;化合物C18ImiHq在LB膜中具有很强的荧光特性,但是当化合物C18ImiHq与Cu2+络合后,其荧光强度则大为减弱。更多还原

【Abstract】 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.更多还原