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Chinese Journal of Organic Chemistry >

2013 , Vol. 33 >Issue 11: 2423 - 2429

DOI: https://doi.org/10.6023/cjoc201305034

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Synthesis and Fluorescent Properties of Peripherally 1,8-Naphthalimide-Labeled Dendron

  • Luo Xiaoyan ,
  • Qian Ying
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  • School of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189

Received date: 2013-05-21

  Revised date: 2013-07-02

  Online published: 2013-07-19

Supported by

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

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Abstract

A novel 1, 8-naphthalimide compound, 4-piperidyl-9-ethylamino-{N，N-bis[ (4-piperidyl-1, 8-naphathlimide)-ethy-laminocarbonylethyl]amino}-1, 8-naphthalimide (BPNAN), was synthesized through acly-nucleophilic substitution reaction and Michael addition reaction based on 4-bromo-1, 8-naphthalic anhydride. The product was characterized by melting point, 1H NMR and HRMS techniques. The photophysical properties were detected. The target compound exhibited strong fluorescence. BPNAN showed red shifts with increasing of the solvent polarity. pH fluorescent probe actions, metal ions and ct-DNA probes were also detected. The fluorescence intensity of BPNAN changed obviously along with pH value and can be applied as pH fluorescent probes. When the ion concentration of Cu2+ was 8 μmol/L, the fluorescence intensity of BPNAN enhanced to 1.2 times of the original one. When the concentration of ct-DNA was up to 500 μg/mL, the fluorescence intensity was the maximum one. In a word, BPNAN is a good kind of fluorescent materials.

Key words： 1,8-naphthalimide; solvatochromism effect; pH fluorescent probe; metal ion probe; DNA probe

Cite this article

Luo Xiaoyan , Qian Ying . Synthesis and Fluorescent Properties of Peripherally 1,8-Naphthalimide-Labeled Dendron[J]. Chinese Journal of Organic Chemistry, 2013 , 33(11) : 2423 -2429 . DOI: 10.6023/cjoc201305034

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