Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (11): 2354-2361.DOI: 10.6023/cjoc201403065 Previous Articles     Next Articles



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 发布日期:2014-07-11
  • 通讯作者: 钱鹰,
  • 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 Published:2014-07-11
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No.61178057).

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