Citation: Niu Yanfang, Qian Ying, Hu Xiudong. Synthesis, Aggregation-Induced Emission Enhancement and Cells Imaging of Water-Soluble Pyridine Naphthalimide-Polyamidoamine Dendrimer[J]. Chinese Journal of Organic Chemistry, ;2016, 36(3): 555-561. doi: 10.6023/cjoc201509045 shu

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

1.
School of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189

Corresponding author: Qian Ying, yingqian@seu.edu.cn
Received Date: 30 September 2015
Revised Date: 6 November 2015

Fund Project: the National Natural Science Foundation of China 61178057

Figures(7)

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