有机化学 ›› 2014, Vol. 34 ›› Issue (11): 2354-2361.DOI: 10.6023/cjoc201403065 上一篇    下一篇

研究简报

一种红光发射三苯胺吡啶盐的合成及荧光探针性质

陶在琴, 钱鹰   

  1. 东南大学化学化工学院 南京 211189
  • 收稿日期:2014-03-30 修回日期:2014-05-26 出版日期:2014-11-25 发布日期:2014-07-11
  • 通讯作者: 钱鹰,yingqian@seu.edu.cn E-mail:yingqian@seu.edu.cn
  • 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

Tao Zaiqin, Qian Ying   

  1. School of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189
  • Received:2014-03-30 Revised:2014-05-26 Online:2014-11-25 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.

关键词: 水溶性吡啶盐, 荧光探针, Heck反应, 红光发射, 荧光性质

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.

Key words: water-soluble pyridine salt, fluorescence probe, Heck reaction, red emission, fluorescence properity