1,8-萘酰亚胺荧光单体的合成、表征与荧光性质

以4-溴-1,8-萘二甲酸酐和乙醇胺为原料,经过路线1(胺化、酰胺化、季铵化)和路线2(酰胺化、胺化、季铵化)分别得到一种水溶性荧光单体4-(N'甲基-1-哌嗪基)-N-羟乙基-1,8-萘二甲酰烯丙基氯季铵盐,总收率分别为51.8%和45.3%。通过单因素实验确定了季铵化反应的最佳合成条件:n(中间体化合物3):n(烯丙基氯)=1:3.5,反应温度50℃,以丙酮为溶剂,反应时间6 h,在此条件下,该步收率达到72.4%。采用红外光谱、质谱及核磁共振氢谱对其结构进行了表征,并对其荧光光谱进行了初步研究。

SYNTHESIS, CHARACTERIZATION AND PROPERTIES OF 1,8-NAPHTHALIMIDE FLUORESCENT MONOMER

A kind of water soluble fluorescent monomer,4-(N'-methyl-1-piperazinylallyl)-N-hydroxy- ethyl-naphthalimide chloride quaternary ammonium salt was synthesized from 4-bromo-1,8-naphthalic anhydride and ethanolamine through amination,amidation and quaterisation(route 1)or through ami- dati0n,amination and quaterisation(route 2)with the overall yield of 51.8% or 45.3%,respectively. The optimum preparation conditions of the third step were obtained as follows,n(compound 3):n (allyl chloride)=1:3.5,reaction temperature 50℃,reaction time 6 h,and acetone as solvent.Un- der these conditions,the yield of this step was 72.4%.The structures of the fluorescent monomer and key intermediates were confirmed by IR,MS and ~1H NMR spectroscopy.The fluorescent spec- trum of the monomer was also studied.