两种新型吲哚啉螺吡喃的合成及其光致变色性质研究

先由对氯苯肼和3-甲基-2-丁酮以浓硫酸为催化剂合成吲哚的衍生物,然后再分别与碘甲烷或碘乙烷通过接枝的方法合成吲哚啉碘化物中间体;再以水杨醛或对氯苯酚为主要原料合成中间产物水杨醛衍生物;最后,由这两种中间体合成了3,3-二甲基-N-甲基-5-氯-6′-溴-8′-硝基吲哚啉螺吡喃和3,3-二甲基-N-乙基-5-氯-6′-氯-8′-硝基吲哚啉螺吡喃。通过实验,确定了最佳的反应条件,如合成温度80℃,反应时间2h等,两种化合物的产率也分别达到了43.6%和39.2%,纯度为99.5%。通过元素分析,红外光谱,核磁共振等手段对合成产物的结构进行了表征,并应用紫外-可见吸收光谱对其光致变色性能进行了考察。

SYNTHESIS OF INDOLINSPIROPYRAN AND RESEARCH OF PHOTOCHROMISM

The wide application of photochromic materials aroused attentions of researchers in recent years.Indole derivatives was synthesized first by 4-chlorophenylhydrazine and 3-methyl-2-butanone with concentrated sulfuric acid as catalyst,and then reacted respectively with methyl iodide or ethyl iodide by grafting method for synthesizing indoline iodide intermediates.The intermediate product of salicylaldehyde derivatives was synthesized next with salicylaldehyde or 4-chlorophenol as main raw materials.Two kinds of unreported indoline spiropyran compounds were got finally by the intermediates mentioned above.They are 3,3-dimethyl-N-methyl-5-chloro-6′-bromo-8′-nitro indoline spiropyran and 3,3-dimethyl-N-ethyl-5-chloro-6′-chloro-8′-nitro indoline spiropyran.Optimal reaction conditions were determined after a large number of experimental comparisons.The yields of two compounds could be 43.6% and 39.2% respectively and the purity could be 99.5% when the temperature was 80 ℃ and the reaction time was 2 h.The intermediates and target products were characterized by elemental analysis,IR,NMR and other means.And their photochromic properties were studied by UV-VIS.