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Spiro N-oxidized pyrrolidone-appended hemicyanine: Synthesis, lower pH-sensing and colormetric temperature sensing
Dyes and Pigments ( IF 4.5 ) Pub Date : 2020-02-05 , DOI: 10.1016/j.dyepig.2020.108261
Lanying Wang , Yongqiang Zhang , Mengqi Yan , Zhiwu Fan , Junlong Zhao

Three novel spiro N-oxidized pyrrolidone-appended hemicyanine derivatives have been synthesized and characterized by 1H NMR, 13C NMR, UV–Vis and HRMS. The molecular structures of spirocyclic dye 2a and its opening-ring product 2aa have been determined by single-crystal X-ray diffraction analysis. The UV–vis spectra show significant solvatochromic behavior of three spirocyclic derivatives, especially in acidic and alkaline solvents. Spirocyclic dye 2a displays an excellent pH dependent behavior and responds linearly to extreme acidic conditions in the pH ranges of 1-4. The absorption spectra studies on opening-ring reaction reveal that acid and heat dual stimulation can induce opening-ring of 2a, which exhibits temperature-responsive linear in the range of 25–45 °C, behaving a colorimetric thermometer sensing. These properties provide the possibility for 2a-c to be used as stimulating response molecule switch.



中文翻译:

Spiro N氧化吡咯烷酮附加的半菁:合成,较低的pH传感和比色温度传感

合成了三种新颖的螺-N-氧化吡咯烷酮半胱氨酸衍生物,并通过1 H NMR,13 C NMR,UV-Vis和HRMS进行了表征。通过单晶X射线衍射分析确定了螺环染料2a及其开环产物2aa的分子结构。UV-vis光谱显示出三种螺环衍生物的显着溶剂变色行为,尤其是在酸性和碱性溶剂中。螺环染料2a表现出出色的pH依赖行为,并且在1-4的pH范围内对极端酸性条件线性响应。关于开环反应的吸收光谱研究表明,酸和热的双重刺激可以诱发2a的开环,该开环在25–45°C的范围内表现出温度响应线性,表现为比色温度计。这些特性为2a-c用作刺激反应分子开关提供了可能性。

更新日期:2020-02-05
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