有机化学 ›› 2013, Vol. 33 ›› Issue (11): 2423-2429.DOI: 10.6023/cjoc201305034 上一篇    下一篇

研究简报

多臂萘酰亚胺树枝分子的合成和荧光性质

罗晓燕, 钱鹰   

  1. 东南大学化学化工学院 南京 211189
  • 收稿日期:2013-05-21 修回日期:2013-07-02 出版日期:2013-11-25 发布日期:2013-07-19
  • 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 and Fluorescent Properties of Peripherally 1,8-Naphthalimide-Labeled Dendron

Luo Xiaoyan, Qian Ying   

  1. School of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189
  • Received:2013-05-21 Revised:2013-07-02 Online:2013-11-25 Published:2013-07-19
  • Supported by:

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

以4-溴-1,8-萘酐为原料,通过亲核取代反应、迈克尔加成反应合成了多臂1,8-萘酰亚胺树形化合物BPNAN (4-piperidyl-9-ethylamino-{NN-bis[(4-piperidyl-1,8-naphathlimide)-ethylaminocarbonylethyl]amino}-1,8-naphthalimide). 化合物经熔点、核磁、高分辨质谱表征,测定了它在不同溶剂中的光物理性质. 目标化合物具有较明显的溶剂效应,其荧光发射峰随溶剂极性的增大向长波方向移动,随着萘酰亚胺基团数目的增长,BPNAN的斯托克斯位移随着溶剂极性的增强有增大的趋势. 测定了BPNAN的pH探针、金属离子探针和DNA荧光探针行为. BPNAN的荧光强度随着pH的增加呈现逐渐增强的变化趋势,可作为pH荧光探针; BPNAN对浓度为8 μmol/L的金属离子Cu2+有较强的感应,溶液的荧光强度加强至原来的1.2倍; BPNAN对小牛胸腺DNA的荧光强度感应呈增大的趋势,当ct-DNA浓度达到500 μg/mL时,荧光强度达到最大. 研究表明多臂萘酰亚胺树形化合物BPNAN是一种性能优良的荧光材料.

关键词: 1,8-萘酰亚胺, 溶剂效应, pH荧光探针, 金属离子探针, DNA荧光探针

A novel 1, 8-naphthalimide compound, 4-piperidyl-9-ethylamino-{NN-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