以对硝基甲苯为起始原料,与NBS经溴代反应制得对溴甲基硝基苯(2);2与亚磷酸三乙酯经取代反应得4-硝基苯基膦酸二乙酯(3);4-醛基苯基亚氨基二乙酸二乙酯与3或对硝基苯乙腈分别经Wittig-Horner反应和Knoevenagel缩合反应合成了两种新型茋类化合物(5和7),其结构经1H NMR,13C NMR,IR和ESI-MS表征。用UV-Vis和荧光光谱研究了5和7的光学性质。结果表明:5和7的最大吸收峰均位于410 nm;5的荧光发射峰位于529 nm,较7红移26 nm,发射强度提高129倍。
1-(Bromomethyl)-4-nitrobenzene (2) was prepared by bromination of p-nitrotoluene with N-bromobutanimide. Diethyl 4-nitrobenzylphosphonate(3) was prepared by substitution reaction of 2 with triethyl phosphite. Two novel compounds (5 and 7) containing stilbene were synthesized by Wit- fig - Homer reaction of diethyl 4-formylphenyliminodiacetate with 3 or Knoevenagel condensation re- action with 4-nitrophenylacetonitrile, respectively. The structures were characterized by 1H NMR, 13C NMR, IR and ESI-MS. The optical properties of 5 and 7 were investigated by UV-Vis and fluo- rescence spectra. The results showed that λmax= of 5 and 7 were 410 rim. Compared with the emission band of 7, 5 presents a red shift of 26 nm(529 nm) and an emission intensity increment of 129 times.