三丹磺酰基取代1,4,7-三氮环壬烷的合成与荧光性质  

Synthesis and Fluorescence Properties of Tridansulfonyl-Substituted 1,4,7-Triazacyclononane

作　　者：方霄 王宇静 汪清清 周婷 王小波[1] FANG Xiao;WANG Yu-jing;WANG Xiao-bo(School of Pharmacy,Xianning Medical College,Hubei University of Science and Technology,Xianning Hubei 437100,China)

机构地区：[1]湖北科技学院医学部药学院,湖北咸宁437100 [2]湖北科技学院核技术与化学生物学院

出　　处：《湖北科技学院学报（医学版）》2022年第5期369-372,共4页Journal of Hubei University of Science and Technology(Medical Sciences)

基　　金：湖北省教育厅重点项目(D20212802)。

摘　　要：目的合成三丹磺酰基-1,4,7-三氮环壬烷(简称TD_(3)),研究其在不同极性溶剂中的荧光光谱。方法以1,4,7-三氮环壬烷盐酸盐和丹磺酰氯为起始原料,通过两步反应制备TD_(3),并以质谱和核磁共振波谱对TD_(3)进行了表征。研究了TD_(3)在DMSO、THF、EtOH、CH_(3)CN四种极性不同的单一溶剂和THF/H_(2)O及DMSO/H_(2)O不同比例下的混合溶剂中的荧光发射光谱。结果在纯有机溶剂中,随着溶剂极性的增强,TD_(3)在溶液中的发射波长逐渐红移。在THF/H_(2)O及DMSO/H_(2)O混合体系中,随着水含量的增加,TD_(3)的发射波长均出现先红移后蓝移的现象。在THF/H_(2)O中,在发射波长红移的同时伴随着荧光强度的降低,但发射波长蓝移时则伴随着荧光强度的增强;而DMSO/H_(2)O体系中则正好相反。结论溶剂的种类与极性对TD_(3)发射波长的变化有明显影响,这将对研究开发丹磺酰类荧光探针尤其是极性探针提供借鉴。Objective To synthesize tridansulfonyl-1,4,7-triazacyclononane(named TD_(3))and investigate its fluorescence characteristics in different polar solvents.Methods TD_(3)was prepared by a two-step reaction using 1,4,7-triazacyclononane hydrochloride and dansyl chloride as the starting materials,and then characterized by mass spectrometry and nuclear magnetic resonance spectroscopy(NMR).The fluorescence emission spectra of TD_(3)was studied in four solvents with different polarities such as DMSO,THF,EtOH and CH_(3)CN,as well as mixed solvents with different ratios of THF/H_(2)O and DMSO/H_(2)O.Results In pure organic solvents,the emission wavelength of TD_(3)was gradually red-shifted with the enhancement of solvent polarity.In the mixed systems of THF/H_(2)O and DMSO/H_(2)O,with the increase of water content,the emission wavelength of TD_(3)showed a red-shift and a blue-shift.The difference was that in THF/H_(2)O was accompanied by a decrease in the fluorescence intensity when the emission wavelength is red-shifted,but when the emission wavelength was blue-shifted,it was accompanied by an increase in the fluorescence intensity.The opposite was true in the DMSO/H_(2)O system.Conclusion The type and polarity of the solvent have a significant effect on the change of the emission wavelength of TD_(3),which will provide a reference for the development of dansyl-based fluorescent probes,especially aiming at polarity microenvironment probes.

关 键 词：丹磺酰胺 1 4 7-三氮环壬烷 溶剂极性 荧光性质 

分 类 号：O641.4[理学—物理化学]