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新型pH敏感吡喃腈衍生物的合成及其荧光性能

周秋璇1,顾培洋2,路建美2*,徐庆锋2,张勇1,2   

  1. (1.苏州大学分析测试中心苏州 215123；2.江苏省节能环保材料测试与技术服务中心 苏州 215123)
  • 收稿日期:2012-07-02 修回日期:2012-10-30 出版日期:2013-05-10 发布日期:2013-05-10
  • 通讯作者: 路建美，教授; Tel:0512-65880368; Fax:0512-65880367; E-mail:lujm@suda.edu.cn; 研究方向：有机及高分子功能材料
  • 基金资助:
    国家自然科学基金（21176164，21071105）资助项目

Synthesis and Fluorescence of a New pH-Sensitive Pyran Nitrile Derivatives

ZHOU Qiuxuan1, GU Peiyang2, LU Jianmei1*, XU Qingfeng2, ZHANG Yong1,2   

  1. (1.Analysis and Testing Center of Soochow University,Suzhou  215123,China;
    2.The Testing and Technical Service Center of Jiangsu Province for Energy-saving and
    Environment-friendly Materials,Suzhou 215123 ,China)
  • Received:2012-07-02 Revised:2012-10-30 Published:2013-05-10 Online:2013-05-10
  • Contact: Jianmei

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被引次数

1

摘要： 以2,6-二甲基-4H-吡喃-4-酮、丙二腈和4-(4-甲酰苯基)吗啉为原料，合成了2种含吡喃腈（DCM）结构的化合物：2-甲基-6-（4-吗啡啉苯乙烯基）-4-二氰甲烯基吡喃（MDCM）和2,6-二（4-吗啡啉苯乙烯基）-4-二氰甲烯基吡喃（BDCM）。 通过1H NMR、元素分析等确定了其结构，并探讨了所得化合物的荧光性能，研究了化合物在不同浓度下荧光强度的变化、溶剂效应对其荧光性能的影响以及酸性条件下荧光光谱的变化。 结果表明，MDCM和BDCM的最大荧光发射波长均在红光区域，2种化合物溶液的最大荧光发射波长随溶剂极性和溶液酸性的增强而发生红移，由于浓度猝灭效应，MDCM和BDCM的DMF溶液浓度分别为1×10-4和1×10-5 mol/L时，荧光发射峰为最强。 又因为BDCM分子的共轭度比MDCM大得多，所以其固体的最大荧光发射波长向长波长移了37 nm。

关键词: DCM, 荧光, 浓度效应, 溶剂效应, pH影响

Abstract: 2-{2-Methyl-6-[2-(4-morpholin-4-yl-phenyl)-vinyl]-pyran-4-ylidene}-malononitrile(MDCM) and 2-{2,6-bis-[2-(4-morpholin-4-yl-phenyl)-vinyl]-pyran-4-ylidene}-malononitrile(BDCM) were synthesized from 2,6-dimethyl-4H-pyran-4-one, malononitrile, 4-(4-formylphenyl)morpholine and piperidine. 1H NMR and elemental analysis were used to characterize two compounds. The fluorescence spectra of the two compounds in solutions with different concentration were investigated. The solvent effects which impact on the fluorescence properties and the characteristics of the fluorescence in acidic solution were also systematically studied. The result show that fluorescence center wavelengthes of both compounds are in the red region, and the spectra exhibit red-shifts with increasing the polarity and acidity of the solvents. It is also found that the derivatives of MDCM and BDCM at concentrations of 1×10-4 mol/L and 1×10-5 mol/L, respectively, exhibit the highest fluorescent intensities. The solid fluorescent maximum wavelength of the BDCM has a 37 nm red-shift longer than that of MDCM, because the conjugate system of BDCM is longer than that of MDCM.

Key words: DCM, fluorescence, concentration quenching effect, solvent effect, pH influence

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