含BOC保护基团的螺吡喃类化合物的合成及其光致变色性能的研究

合成了5-N-(叔丁氧甲酰基)氨基]-1,3,3-三甲基-6′-硝基吲哚啉螺吡喃(BOCSPI)和5-N-(叔丁氧甲酰基)氨基]-1,3,3-三甲基-6′-硝基-8′-甲氧基吲哚啉螺吡喃(BOCSPII)两种光致变色化合物,采用紫外-可见光谱法研究了其在溶液和以不同质量比掺杂在聚甲基丙烯酸甲酯(PMMA)膜中的光致变色性能.研究表明螺吡喃的高掺杂量不利于其开环和闭环态的转化,BOCSPII分子中的甲氧基有利于有色开环体的部花菁的稳定.

Synthesis of Spiropyran with BOC Protective Function and Research of Photochromism

Two indolinebenzopyran derivatives, 5-Amino-N-(tert-butyloxycarbon-yl)-1,3,3-trimethyl-6′-nitro-spiro(indole-2,2′-2H-1]benzopyran) (BOCSPI) and 5-Amino-N-(tert-butyloxycarbonyl)-1,3,3-trimethyl-6′-nitro-8′-methoxy-spiro(indole-2,2′-2H-1]benzopyran) (BOCSPII), were synthesized and characterized. BOCSPI and BOCSPII were doped in polymethylmethacrylate (PMMA) host films with different concentration respectively. The photochromic properties of the two compounds in solution and film were investigated. It has been found that both the rate of photo-colorization from the closed form(SP) to open form(MC) and the rate of thermal isomerization between the closed form(SP) to the open form(MC) decreased remarkably with the increase of the concentration of spiopyran derivatives in PMMA film. The existence of 8′-methoxy group in BOCSPII made the opened form MC more stable at room temperature.