高等学校化学学报 ›› 2009, Vol. 30 ›› Issue (8): 1516.

• 研究论文 • 上一篇    下一篇

新型4-羟基香豆素衍生物的微波合成及其光谱性质

董社英1, 李靖1, 黄廷林2   

  1. 1. 西安建筑科技大学理学院,
    2. 环境与市政工程学院, 西安 710055
  • 收稿日期:2008-07-17 出版日期:2009-08-10 发布日期:2009-08-10
  • 通讯作者: 董社英, 女, 博士, 教授, 主要从事应用化学及电化学分析研究. E-mail: dongsyy@126.com
  • 基金资助:

    陕西省自然科学基础研究基金(批准号: 2005B28)资助.

Microwave-induced Synthesis and Spectral Properties of New 4-Hydroxycoumarin Derivatives

DONG She-Ying1*, LI Jing1, HUANG Ting-Lin2   

  1. 1. College of Sciences,
    2. School of Environment and Municipal Engineering, Xi′an University of Architecture and Technology, Xi′an 710055, China
  • Received:2008-07-17 Online:2009-08-10 Published:2009-08-10
  • Contact: DONG She-Ying. E-mail: dongsyy@126.com
  • Supported by:

    陕西省自然科学基础研究基金(批准号: 2005B28)资助.

摘要:

以4-羟基香豆素(a)为原料微波辐射合成了具有独特的生理活性和荧光性能的3,3′,3″,3′″-亚乙四基-4-羟基香豆素(b)、3,3′-苯亚甲基-双-4-羟基香豆素(c)和4-羟基香豆素-1,4-萘醌(d)系列4-羟基香豆素衍生物, 采用元素分析、红外光谱、核磁共振及质谱表征了产物的结构, 并对其紫外-可见吸收光谱及荧光光谱性质进行了研究, 探索了化合物的微观结构与其光学性能之间的关系. 研究结果表明, 具有“近平面”、大π共轭和对称型结构的化合物b具有较大的摩尔吸光系数及强荧光特性, 且浓度在0.50~1.50×10-4 mol/L范围时, 其荧光强度随着浓度的降低而呈线性增加; 在pH=1.81~6.09时, 荧光强度随pH降低而减弱, 在pH 8.36~11.98时, 荧光强度随pH升高而减弱. 此外, 牛血清白蛋白(BSA)及脱氧核糖核酸(DNA)可与该化合物发生相互作用, 进而敏化增强该分子的内源荧光.

关键词: 4-羟基香豆素衍生物; 微波辐射; 紫外-可见吸收光谱; 荧光光谱

Abstract:

Three kinds of 4-hydroxycoumarin derivatives, 3,3′,3″,3″′-ethylenetetrakis-4-hydroxycoumarin(b), 3,3′-benzylidenedi-4-hydroxycoumarin(c) and 4-hydroxycoumarin-1,4-naphthaquinone(d) were synthesized from 4-hydroxycoumarin(a) under microwave irradiation and characterized by means of elemental analysis, IR, 1H NMR and MS. The compounds a—d were studied by ultraviolet-visible absorption spectra and fluorescence spectroscopy. It was confirmed that the big π-conjugated, symmetrical compound b had better fluorescence in solution and possessed high molar extinction coefficient. When the concentration of compound b was in the range of 0.50—1.50×10-4 mol/L, the fluorescence intensity linearly increased with decreasing concentration. In the range of pH=1.18—6.09, fluorescence intensity increased with increasing of pH, and in the range of pH=8.36—11.98 fluorescence intensity increased with decreasing of pH values. In addition, fluorescence enhancing was significantly observed in the presence of BSA and DNA.

Key words: 4-Hydroxycoumarin derivative; Microwave-induced synthesis; Ultraviolet-visible absorption spectra; Fluorescence spectrum

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