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Spiropyran-azobenzene-DBU system as solvent indicator
Tetrahedron Letters ( IF 1.8 ) Pub Date : 2018-07-10 , DOI: 10.1016/j.tetlet.2018.07.025
Zhiping Xu , Shen Li , Yujun Shen , Meijun Chen , Xusheng Shao

A dyad bearing azobenzene and spiropyran units was synthesized and its applications in indicating the polarity and protic or aprotic properties of a solvent were explored. The spiropyran-azobenzene derivative (SPAB) can be induced to different forms in different miscellaneous solvents accompanied with different color changes and spectral characteristics at the presence of organic base DBU. In a nonpolar or low-polar solvent, SPAB exists in thermostable spiropyran form with yellow color output. While in an aprotic polar solvent, the spiropyran part isomerized to merocyanine form giving a blue color. When SPAB is subjected to a protic solvent, the alkylation reaction occurs at the oxygen generating the alkylated-SPAB with red color. This solvent-dependent property can be used for discriminating solvent type.



中文翻译:

Spiropyran-偶氮苯-DBU系统作为溶剂指示剂

合成了带有偶氮苯和螺吡喃单元的二联体,并探讨了其在指示溶剂的极性和质子或非质子性质中的应用。在有机碱DBU的存在下,螺吡喃-偶氮苯衍生物(SPAB)在不同的杂溶剂中可以诱导成不同的形式,并伴随着不同的颜色变化和光谱特征。在非极性或低极性溶剂中,SPAB以热稳定的螺并吡喃形式存在,输出黄色。在非质子极性溶剂中,螺吡喃部分被异构化为花青形式,产生蓝色。当SPAB受到质子溶剂作用时,烷基化反应在氧气处发生,从而生成红色的烷基化SPAB。这种取决于溶剂的特性可用于区分溶剂类型。

更新日期:2018-07-10
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