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首页> 外文期刊>Bulletin of the Chemical Society of Japan >Synthesis and Properties of Photochromic Diarylethenes with Heterocyclic Arly Groups
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Synthesis and Properties of Photochromic Diarylethenes with Heterocyclic Arly Groups

机译：具有杂环Arly基的光致变色二硫杂环丁烷的合成与性能

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摘要

A new class of thermally irreversible and fatigue resistant photochromic molecules named diarylethenes has been developed. Theoretical consideration based on the state correlation diagrams of electrocyclic reactions revealed that the thermal irreversibility is attained by introducing aryl groups that have low aromatic stabilization energy. According to the molecular design principle thermally irreversible photochromic diarylethenes having heterocyclic five-membered rings, such as furan, thiophene (or benzothiophene), or thiazole rings, have been newly synthesized. Among them, diarylethenes having benzothiophene aryl groups showed an excellent fatigue resistant property.They underwent photochromic cycles more than 1.0 * 10~4 times. The absorption maxima of the closed-ring forms varied from 425 to 828 nm depending on the aryl groups, substituents of the aryl groups, and the substitution position of the aryl groups to the ethane moiety. The response times of both cyclization and ring-opening reactions were less than 10 ps in solution as well as in a crystalline phase. The chemical and thermal control of photochromic reactivity was achieved by introducing intramolecular hydrogen bonding groups or oligothiophene aryl groups to the diarylethenes. Some of the dithienylperfluorocyclopentene derivatives were found to show photochromic reactivity in the crystalline phase. The reactivity was dependent on the conformation and molecular packing in the crystals.
机译：已经开发出一种新型的热不可逆且抗疲劳的光致变色分子，称为二芳烃。基于电环反应的状态相关图的理论考虑表明，通过引入具有低芳族稳定能的芳基可以达到热不可逆性。根据分子设计原理，已经新合成了具有杂环五元环如呋喃，噻吩（或苯并噻吩）或噻唑环的热不可逆的光致变色二蒽。其中，具有苯并噻吩芳基的二芳烃具有优异的抗疲劳性能，经历了1.0 * 10〜4倍的光致变色循环。取决于芳基，芳基的取代基和芳基对乙烷部分的取代位置，闭环形式的吸收最大值在425至828nm之间变化。在溶液中以及在结晶相中，环化和开环反应的响应时间均小于10 ps。通过将分子内的氢键基团或低聚噻吩芳基基团引入二芳烃中来实现对光致变色反应性的化学和热控制。发现一些二噻吩基全氟环戊烯衍生物在结晶相中显示出光致变色反应性。反应性取决于晶体中的构象和分子堆积。

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