Comparative Evaluation of Substituent Effect on the Photochromic Properties of Spiropyrans and Spirooxazines,The Journal of Organic Chemistry

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Comparative Evaluation of Substituent Effect on the Photochromic Properties of Spiropyrans and Spirooxazines
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2016-09-21 00:00:00 , DOI: 10.1021/acs.joc.6b01193
Edward I. Balmond ₁ , Brandon K. Tautges ₁ , Andrea L. Faulkner ₁ , Victor W. Or ₁ , Blanka M. Hodur ₁ , Jared T. Shaw ₁ , Angelique Y. Louie ₂

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Spiropyrans and spirooxazines represent an important class of photochromic compounds with a wide variety of applications. In order to effectively utilize and design these photoswitches it is desirable to understand how the substituents affect photochromic properties, and how the different structural motifs compare under identical conditions. In this work a small library of photoswitches was synthesized in order to comparatively evaluate the effect of substituent modifications and structure on photochromism. The library was designed to modify positions that were believed to have the greatest effect on C–O bond lability and therefore the photochromic properties. Herein we report a comparative analysis of the UV and visible light responses of 30 spiropyrans, spiroindolinonaphthopyrans, and spirooxazines. The influence of gadolinium(III) binding was also investigated on the library of compounds to determine its effect on photoswitching. Both assays demonstrated different trends in substituent and structural requirements for optimal photochromism.

中文翻译：

取代基对螺旋藻和螺恶嗪光致变色性能影响的比较评估

螺吡喃和螺恶嗪代表一类重要的光致变色化合物，具有广泛的应用。为了有效地利用和设计这些光开关，需要了解取代基如何影响光致变色特性，以及在相同条件下如何比较不同的结构基序。在这项工作中，合成了一个小的光电开关库，以比较评估取代基修饰和结构对光致变色的影响。该文库旨在修饰据认为对C-O键不稳定性以及因此对光致变色性质影响最大的位置。本文中，我们报告了30种螺吡喃，螺吲哚并萘并螺恶嗪的紫外线和可见光响应的比较分析。还研究了ado（III）结合对化合物库的影响，以确定其对光开关的影响。两种测定均显示出取代基和最佳光致变色结构要求的不同趋势。

更新日期：2016-09-21

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