Synthesis and Photochemistry of Photochromic Compounds having Independent Functions

具有独立功能的光致变色化合物的合成与光化学

基本信息

批准号：
02640334
负责人：
KURITA Yukio
金额：
$ 1.28万
依托单位：
Yokohama National University
依托单位国家：
日本
项目类别：
Grant-in-Aid for General Scientific Research (C)
财政年份：
1990
资助国家：
日本
起止时间：
1990 至 1991
项目状态：
已结题

项目摘要

Fulgide is one of the most promising candidate to be applied to the erasable-and-rewritable photomemory. We have synthesized several fulgides and studied the relation between the molecular structure including the reaction media and the photochromic properties and obtained highly efficient photochromic fulgides with the large coloring as well as bleaching quantum yields. Recently we have tried to lengthen the absorption maximum of the colored form of fulgides and to develop the nondestructive read-out method, which is the most difficult problem to be solved in order to materialize the photochromic optical memory.Synthesis of fulgide E ; (E) -3- [2- (5-dimethylamino-1, 2-dimethylindol-3-yl) ethylidene] -4-isopropylidene-3, 4-dihydrofuran-2, 5-dione ; was performed by Stobbe condensation of the corresponding substituted indole with diethyl isopropylidenesuccinate followed by hydrolysis and intramolecular acid anhydride formation processes. It has two distinctive characteristics : (i) the colored form (C) has the longest absorption maximum wavelength ever known as that of fulgid : (ii) the bleaching quantum yield of C is negligibly small. By adding strong acids such as trichloroacetic acid to a toluene solution, the protonation occured on the nitroge atom of the dimethylamino group to give EH or CH form. The latter recovered the photochromic nature to return to the bleached form EH. Because an equilibrium of rapid proton exchange exists between C, CH, E, and EH, the C and CH mixture entirely bleached to produce an E ad EH mixture. Similar reaction was observed in polymer films containing the fulgide and the acid. We suggest that the fulgide and trichloroacetic acid combination provides a model of a simple and efficient re-writable optical memory possessing non-destructive read-out ability. Namely, 554 nm light could be used for writing (or erasing), 403 nm light for erasing, and 780 nm light for non-destructive read-out.

Fulgide是最有希望应用于可擦除和可重写光存储器的候选者之一。我们合成了多种俘精酸酐，并研究了包括反应介质在内的分子结构与光致变色性能之间的关系，获得了具有大着色和漂白量子产率的高效光致变色俘精酸酐。最近我们试图延长俘精酸酐有色形式的吸收最大值并开发无损读出方法，这是实现光致变色光学存储器最难解决的问题。 (E)-3-[2-(5-二甲基氨基-1，2-二甲基吲哚-3-基)亚乙基]-4-异亚丙基-3，4-二氢呋喃-2，5-二酮；通过相应的取代吲哚与异亚丙基琥珀酸二乙酯的Stobbe缩合，然后进行水解和分子内酸酐形成过程来进行。它具有两个显着特征：(i) 有色形式 (C) 具有已知的最长吸收最大波长，即 fulgid：(ii) C 的漂白量子产率小得可以忽略不计。通过将强酸如三氯乙酸添加到甲苯溶液中，二甲氨基的氮原子上发生质子化，得到EH或CH形式。后者恢复了光致变色性质，恢复到漂白形式 EH。由于 C、CH、E 和 EH 之间存在快速质子交换平衡，因此 C 和 CH 混合物完全漂白，产生 E 和 EH 混合物。在含有俘精酸酐和酸的聚合物膜中观察到类似的反应。我们认为，俘精酸酐和三氯乙酸的组合提供了一种简单有效的可重写光学存储器模型，具有无损读出能力。即，554 nm 光可用于写入（或擦除），403 nm 光可用于擦除，780 nm 光可用于非破坏性读出。