基于螺[口恶]嗪光异构化的多功能荧光染料及应用  

Multifunctional Fluorescent Dyes based on Spirooxazine Photoisomerization and Its Applications

作　　者：刘箫音 杨素华 张寒 魏云杰 王会东 辛景凡 曹瑞 LIU Xiao-yin;YANG Su-hua;ZHANG Han;WEI Yun-jie;WANG Hui-dong;XIN Jing-fan;CAO Rui(Inner Mongolia Key Laboratory of Photoelectric Functional Materials,College of Chemistry and Life Sciences,Chifeng university,Chifeng 024000,China)

机构地区：[1]赤峰学院化学与生命科学学院内蒙古自治区光电功能重点实验室,内蒙古赤峰024000

出　　处：《化学试剂》2024年第1期45-52,共8页Chemical Reagents

基　　金：内蒙古自然科学基金项目(2023LHMS02013);国家级大学生创新训练项目(202310138005);内蒙古自治区高等学校科学研究项目(NJZY22163);内蒙古自然科学基金项目(2023LHMS02009)。

摘　　要：合成了键合萘酰亚胺单元的螺嗪类化合物,通过核磁共振谱和高分辨质谱确证了其结构。紫外光照射后,化合物能发生从浅黄色到绿色开环体的异构化反应,同时萘酰亚胺单元的荧光强度有所降低。化合物在H^(+)存在时经紫外光照射后发生从浅黄色变为橙色或红色的颜色改变(生成MCH+),其最大吸收波长与萘酰亚胺单元的荧光发射波长具有很好的交叠,发生明显的荧光共振能量转移(FRET),可见光能使逆过程发生伴随着颜色和荧光的恢复,这些结果赋予化合物紫外光/可见光交互作用下的可逆荧光分子开关功能。化合物在滤纸上氢离子存在或缺失条件下的颜色及荧光改变的区别,显示了化合物在多重防伪领域中的应用潜力。A novel spiroxazine compound with naphthalimide unit was synthesized and its structure was confirmed by NMR and HRMS.The solution color of compound changes from light yellow(SO form)to green(MC form)once they are subjected to ultraviolet(UV)irradiation,accompanied by a certain decrease in the fluorescence intensity of the naphthalimide unit.The compound undergoes a color change from light yellow to orange or red(another type of open ring form MCH+)upon UV irradiation in the presence of H+.The maximum absorption wavelength of MCH can overlap with the emission wavelength of the naphthalimide unit at 500~550 nm.Thus,fluorescence resonance energy transition(FRET)may happen between the MCH and 1,8-naphthalimide units,while the reverse isomerization will be conducted with visible light accompanied by recovery of color and fluorescence.The results indicates that the compound exhibits excellent fluorescence molecular switching function under the interaction of UV and Vis.The color and fluorescence changes of the compound in the presence or absence of hydrogen ions in filter paper were tested,demonstrating its potential application in multiple anti-counterfeiting fields.

关 键 词：螺[口恶]嗪 光致变色 萘酰亚胺 酸致变色 荧光共振能量转移 

分 类 号：O657.3[理学—分析化学]