高等学校化学学报

高等学校化学学报 ›› 2012, Vol. 33 ›› Issue (10): 2184.doi: 10.7503/cjcu20120082

• 分析化学 • 上一篇    下一篇

2[(N-乙基)-1-吩噻嗪基]腙的合成及聚集荧光增强性能

曹霞1, 曾晞1, 牟兰1, 陈义1, 王瑞晓1, 张云黔1, 张建新2, 卫钢3   

  1. 1. 贵州大学贵州省大环化学及超分子化学重点实验室, 贵阳 550025;
    2. 中国科学院贵州省天然产物化学 重点实验室, 贵阳 550002;
    3. 澳大利亚联邦科学与工业研究组织, 材料科学与工程分部, 新南威尔士州 2070
  • 收稿日期:2012-01-19 出版日期:2012-10-10 发布日期:2012-09-12
  • 通讯作者: 牟 兰, 女, 博士, 教授, 主要从事光谱分析研究. E-mail: sci.lmou@gzu.edu.cn; 卫 钢, 男, 博士, 教授, 主要从事有机材料研究. E-mail: gang.wei@csiro.au E-mail:sci.lmou@gzu.edu.cn;gang.wei@csiro.au
  • 基金资助:

    国家自然科学基金(批准号: 21165006); 教育部"春晖计划"项目(批准号: Z2009-1-52001); 贵州省国际合作项目基金(批准号: 20107002)和贵州大学研究生创新基金(批准号: 2011048)资助.

Synthesis, Characterization and Aggregation Induced Enhanced Emission of New Phenothiazine Hydrazone

CAO Xia1, ZENG Xi1, MU Lan1, CHEN Yi1, WANG Rui-Xiao1, ZHANG Yun-Qian1, ZHANG Jian-Xin2, WEI Gang3   

  1. 1. Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang 550025, China;
    2. The Key Laboratory of Chemistry for Natural Products of Guizhou Province and Chinese Academy of Sciences, Guiyang 550002, China;
    3. CSIRO Materials Science and Engineeing, Lindfeld, NSW 2070, Australia
  • Received:2012-01-19 Online:2012-10-10 Published:2012-09-12

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摘要：

以氮-氮单键连接2个吩噻嗪环构成共轭结构, 合成了2[(N-乙基)-1-吩噻嗪基]腙, 并对其进行了结构表征. 该化合物在四氢呋喃溶剂中呈分散态时无荧光; 在四氢呋喃/水混合溶剂中呈现聚集荧光增强. 荧光增强是由于聚集态中分子内单键旋转受分子堆积效应的阻碍, 氮-氮单键连接的2个吩噻嗪环趋于平面化以及J-聚集体形成的协同作用使非辐射跃迁减少所致. 同时, 利用这种聚集荧光增强性质考察了该化合物对血红蛋白的探针识别性能.

关键词: 2[(N-乙基)-1-吩噻嗪基]腙, 聚集荧光增强, 分子内旋转受限, 荧光探针

Abstract:

2[(N-ethyl)-1-phenothiazinyl]hydrazone was synthesized and characterized by 1H NMR, IR, ESI-MS and X-ray diffraction. This compound didn’t display obviously fluorescence emission in THF solution; however, it showed aggregation in THF/H2O mixture solvent with the fluorescence intensity enhancement markedly. The crystal structure, fluorescence spectra, SEM and fluorescence microscope results suggested that the fluorescence intensity enhancement was attributed to the intramolecular single bond rotation was hindered by the effects of molecular stacking, the two phenothiazine rings linked by N-N bond went plane and the J-aggregates produced synergistic effects, which abated the nonradiative transition. At the same time, it showed high recognition ability for the detection of hemoglobin in neutral solution with fluorescence enhancement.

Key words: 2[(N-ethyl)-1-phenothiazinyl]hydrazone, Aggregation induced emission enhancement, Restriction of intramolecular rotation, Fluorescence probe

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