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

doi:10.6023/cjoc201509045

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

Articles

水溶性吡啶萘酰亚胺-聚酰胺-胺荧光树形分子的合成、聚集诱导荧光增强及细胞成像

牛艳芳, 钱鹰, 胡秀东

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 E-mail:yingqian@seu.edu.cn
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

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).

1. Synthesis, Aggregation-Induced Emission Enhancement and Cells Imaging of Water-Soluble Pyridine Naphthalimide-Polyamidoamine Dendrimer.PDF(333KB)

Abstract

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

Cite this article

Niu Yanfang, Qian Ying, Hu Xiudong. Synthesis, Aggregation-Induced Emission Enhancement and Cells Imaging of Water-Soluble Pyridine Naphthalimide-Polyamidoamine Dendrimer[J]. Chin. J. Org. Chem., 2016, 36(3): 555-561.

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水溶性吡啶萘酰亚胺-聚酰胺-胺荧光树形分子的合成、聚集诱导荧光增强及细胞成像

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

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