Photoreversible Photographic Systems. VI. Reverse Photochromism of 1,3,3-Trimethylspiro[indoline-2,2′-benzopyran]-8′-carboxylic Acid
Photoreversible Photographic Systems. VI. Reverse Photochromism of 1,3,3-Trimethylspiro[indoline-2,2′-benzopyran]-8′-carboxylic Acid
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VI. 1,3,3-三甲基螺[二氢吲哚-2,2-苯并吡喃]-8-羧酸的逆光致变色
DOI：
10.1246/bcsj.42.1730
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发表时间：
1969
影响因子：
4
通讯作者：
E. Inoue
中科院分区：
文献类型：
--
作者：
I. Shimizu;H. Kokado;E. Inoue
1，3，3-三甲基螺[吲哚啉-2，2 ′-苯并吡喃]（1）的许多衍生物在有机溶剂中表现出光可逆的颜色变化。其中一种衍生物1，3，3-三甲基螺[吲哚啉-2，2 ′-苯并吡喃]-8′-羧酸（2）在极性溶剂中显示“反向光致变色”。化合物2在极性溶剂中呈现深颜色，并且通过用可见光或紫外光照射而脱色。当照射停止时，颜色热再现。从无色形式到有色形式的热转化率取决于溶剂。另一方面，异构体1，3，3-三甲基螺[二氢吲哚-2，2 ′-苯并吡喃]-6′-羧酸在通常条件下既不显示正常光致变色也不显示反向光致变色，但当将酸如丙二酸加入溶液中时显示反向光致变色。由于分子内质子转移，化合物2被认为具有汞染料样结构。
Many derivatives of 1,3,3-trimethylspiro[indoline-2,2′-benzopyran] (1) exhibit photoreversible color changes in organic solvents. One of the derivatives 1,3,3-trimethylspiro[indoline-2,2′-benzopyran]-8′-carboxylic acid (2) shows “reverse photochromism” in polar solvents. The compound 2 exhibits a deep color in the polar solvent and the color is bleached by irradiation with either visible or ultraviolet light. The color reappears thermally as the irradiation is ceased. The thermal conversion rate from the colorless form to the colored one depends on the solvents. On the other hand, the isomer 1,3,3-trimethylspiro[indoline-2,2′-benzopyran]-6′-carboxylic acid shows neither normal nor reverse photochromism under usual conditions, but exhibits reverse photochromism when acid such as malonic acid is added into the solution. The compound 2 is assumed to have a merocyanine dye-like structure due to the intramolecular proton transfer.