吲哚啉螺萘并(噁)嗪光致变色化合物的合成研究

以β-萘酚经亚硝化反应得到中间体1-亚硝基-2-萘酚;以苯肼、3-甲基-2-丁酮为原料合成得到2,3,3-三甲基-3H-吲哚,经碘甲烷季铵盐化后在碱性条件下与1-亚硝基-2-萘酚反应得到1,3,3-三甲基吲哚啉螺萘并(噁)嗪光致变色化合物.通过1H NMR、IR和元素分析确证了中间体和目标分子的结构;讨论了温度对1-亚硝基-2-萘酚合成的影响、制备吲哚季铵盐时溶剂的选择以及目标化合物的合成与光致变色机理.目标化合物的甲醇溶液经紫外光照射后由无色变为淡兰色,显示了良好的光致变色性能.

Synthesis and study on photochromic compound indolinespironaphthooxazine

1-nitroso-2-naphthol was synthesized from 2-naphthol by nitrosation;Using phenylhydrazine and 3-methyl-2-butanone as main materials,2,3,3-tri-methyl-3H-indole was prepared,after quaterizing with iodomethane,reacting with 2-hydroxy-1-naphthaldehyde under basic condition,the target compound 1,3,3-trimethylindolinespironaphthooxazine was got.The structures of important intermediate and target compound was determined by()~1H NMR.,IR and elemental analysis.The effect of temperature on synthesis of 1-nitroso-2-naphthol and selection of solutions in preparing the indole quaternary ammonium salt and the synthetic mechanism of target compound and its photochromic mechanism were discussed.The color of target compound in methanol solution changed from colorless to pale blue after irradiated by UV,which indicated a better photochromic property.