Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (3): 555-561.DOI: 10.6023/cjoc201509045 Previous Articles     Next Articles



牛艳芳, 钱鹰, 胡秀东   

  1. 东南大学化学化工学院 南京 211189
  • 收稿日期:2015-09-30 修回日期:2015-11-06 发布日期:2015-11-26
  • 通讯作者: 钱鹰
  • 基金资助:

    国家自然科学基金(No. 61178057)资助项目.

Synthesis, Aggregation-Induced Emission Enhancement and Cells Imaging of Water-Soluble Pyridine Naphthalimide-Polyamidoamine Dendrimer

Niu Yanfang, Qian Ying, Hu Xiudong   

  1. School of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189
  • Received:2015-09-30 Revised:2015-11-06 Published:2015-11-26
  • Supported by:

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

A water-soluble pyridine naphthalimide-polyamidoamine dendrimer (PN-PAMAM) was synthesized by the amidation reaction of 4-(2-vinylpyridine)-1,8-naphthalimide unit and the polyamidoamine (PAMAM). The structure was characterized by 1H NMR, 13C NMR, IR and HRMS techniques. PN-PAMAM displayed obvious aggregation-induced emission enhancement (AIEE) behavior. The experimental results demonstrated that dendrimer PN-PAMAM in solid state emitted a yellow-green fluorescence and the maximum emission wavelength was 532 nm. In aqueous solution the maximum emission wavelength was 494 nm and the fluorescence quantum yield was 4.42%. The fluorescence intensity reached the maximum at 60% water volume fraction in H2O/THF mixed solution. The fluorescence emission wavelength was 485 nm and the fluorescence quantum yield was increased to 17.54%. The photophysical properties of the silica nanoparticles loaded AIEE dye PN-PAMAM were examined. The fluorescence emission wavelength was 473 nm and the particle diameter was about 40 nm. In addition, dendrimer PN-PAMAM were applied for breast cancer MCF-7 cells imaging, getting clear blue-field photograph. In summary, the pyridine naphthalimide-PAMAM dendrimer is a water-soluble fluorescent dye and displays AIEE behavior. PN-PAMAM can be widely used in areas of tumor localization, bio-tracking and nano-materials.

Key words: pyridine naphthalimide-PAMAM dendrimer, water-soluble fluorescent molecule, aggregation-induced emission, nanoparticles, cells imaging