引用本文:
刘平, 明阳福, 俞君, 樊美公. 9'-(4-烯丙氧基苯甲酰氧基)吲哚啉螺萘并嗪的合成及其光谱性质[J]. 应用化学,
1999, 16(4): 14-19.
Citation: Liu Ping, Ming Yangfu, Yu Jun, Fan Meigong. Syntheses and Spectral Properties of 9'-(4-(Allyloxy) benzoxy)indolinospironaphthoxazine Derivatives[J]. Chinese Journal of Applied Chemistry, 1999, 16(4): 14-19.
Citation: Liu Ping, Ming Yangfu, Yu Jun, Fan Meigong. Syntheses and Spectral Properties of 9'-(4-(Allyloxy) benzoxy)indolinospironaphthoxazine Derivatives[J]. Chinese Journal of Applied Chemistry, 1999, 16(4): 14-19.
9'-(4-烯丙氧基苯甲酰氧基)吲哚啉螺萘并嗪的合成及其光谱性质
摘要:
合成了7种9'-羟基吲哚啉螺萘并嗪衍生物(HSPa~g)和7种9'-(4-烯丙氧基苯甲酰氧基)吲哚啉螺萘并嗪衍生物(ASPa~g).ASPa~g的1H NMR结果表明,当1位是苄基或乙基时,与氮相连的亚甲基的2个氢的化学位移不等价,属AB自旋系统.此外随溶剂极性增加,ASPa~g的萘并嗪环部分的吸收发生蓝移.吲哚啉环氮原子上的取代基的变化对螺嗪(ASPa)在295 nm处的吸收无明显影响,但当5位上的氢被甲基和氯取代时,此处的吸收发生红移.除ASPe的萘并嗪环部分的吸收红移外,吲哚环氮原子和5位上的取代基的变化对螺嗪的萘并嗪环部分吸收无明显影响,但使成色体的吸收红移.
English
Syntheses and Spectral Properties of 9'-(4-(Allyloxy) benzoxy)indolinospironaphthoxazine Derivatives
Abstract:
Seven 9'-hydroxyindolinospironaphthoxazine derivatives(HSPa~g) and seven corresponding 9'-(4-(allyloxy)benzoxy)indolinospironaphthoxazine derivatives(ASPa~g) were synthesized. The 1H NMR results of ASPa~g showed that the chemical shifts of two protons of methene at 1-position of ASPe and ASPb are not equal and the two protons belong to AB spin system. In addition, the absorption spectra of the naphthoxazine moiety are slightly blue shifted with increase of the polarity of the solvent used. The substituents at 1-position have little effect on the absorption spectrum at 295 nm in the parent compound ASPa, and only absorption spectrum of the naphthoxazine moiety of ASPe is found to be red-shifted. A change of substitutent at 5-position, such as in the case of 5-methyl and 5-chloro derivatives, results in the red-shift of absorption band at 295 nm, but does not much influence the absorption spectrum of naphthoxazine moiety. The substituent change at 5-position affects absorption spectrum of the colored forms in the visible region and induces a bathochromic shift.
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Key words:
- spiroxazine
- / photochromism
- / 1H NMR
- / absorption spectrum
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