一种红光发射三苯胺吡啶盐的合成及荧光探针性质  

Systhesis and Fluorescence Probe Properities of Red-Emission Triphenylamine-Pyridinium Salt

作　　者：陶在琴 钱鹰[1] 

机构地区：[1]东南大学化学化工学院,南京211189

出　　处：《有机化学》2014年第11期2354-2361,共8页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No.61178057)资助项目~~

摘　　要：以双碘代芳醛4-[N,N-二（4-碘苯基）氨基]苯甲醛与4-乙烯基吡啶通过钯催化双位点Heck偶联反应制备了中间体TPAPy, TPAPy再与碘代十八烷反应得到吡啶盐衍生物TPAPyS.目标化合物的结构经过红外光谱、核磁共振谱、高分辨质谱确认,测定了吡啶盐TPAPyS在固态、水溶液中及乙醇/水混合溶液中的荧光光谱.吡啶盐TPAPyS在固体状态下发出暗红色荧光,荧光发射峰为654 nm,测得固体量子产率为3.83%. TPAPyS 在水溶液中发出红色荧光,荧光发射峰为647 nm.在乙醇/水混合溶液中,化合物TPAPyS的荧光发射峰位于612～640 nm.测定了吡啶盐TPAPyS与牛血清蛋白（BSA）、胱氨酸（DCys）及半胱氨酸（Cys）在生理条件下的光谱行为,吡啶盐TPAPyS与BSA、氨基酸作用后荧光发射强度均增加.吡啶盐 TPAPyS 是一种可溶于水的红光发射材料,荧光发射峰位于近红外波段,可作为荧光探针用于牛血清蛋白和氨基酸的检测.Intermediate TPAPy was synthesised by vinyl-pyridine and 4-[N,N-bis（4-iodophenyl）amino]benzaldehyde through double-pot Heck reaction, then iodooctadecane was introduced to pyridyl forming the final pyridine salt TPAPyS. The structure of final salt was characterized by 1H NMR, 13C NMR, IR and HRMS-MALDI-TOF. Its fluorescence property was examined. Pyridine salt TPAPyS emits dark red fluorescence with peaks at 654 nm in solid state. The solid-state quantum yield of TPAPyS is 3.83%. TPAPyS emits red fluorescence with peaks at 647 nm in pure water and 612~640 nm in etha-nol/H2O mixture solution. The spectra of TPAPyS with or without BSA, dicysteine, cysteine were measured. The maxima fluorescence emission intensity of water-soluble pyridine salt TPAPyS is enhanced after combining with BSA, dicysteine and cysteine. Pyridine salt TPAPyS is water-soluble with fluorescence spectra in near-infrared region, and it can be used as fluorescence probe to detect BSA, DCys and Cys.

关 键 词：水溶性吡啶盐 荧光探针 HECK反应 红光发射 荧光性质 

分 类 号：O657.3[理学—分析化学] O626.32[理学—化学]