一种红光发射三苯胺吡啶盐的合成及荧光探针性质
收稿日期: 2014-03-30
修回日期: 2014-05-26
网络出版日期: 2014-07-11
基金资助
国家自然科学基金(No.61178057 )资助项目.
Systhesis and Fluorescence Probe Properities of Red-Emission Triphenylamine-Pyridinium Salt
Received date: 2014-03-30
Revised date: 2014-05-26
Online published: 2014-07-11
Supported by
Project supported by the National Natural Science Foundation of China (No.61178057).
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.
陶在琴 , 钱鹰 . 一种红光发射三苯胺吡啶盐的合成及荧光探针性质[J]. 有机化学, 2014 , 34(11) : 2354 -2361 . DOI: 10.6023/cjoc201403065
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 ethanol/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.
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