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2[(N-乙基)-1-吩噻嗪基]腙的合成及聚集荧光增强性能
引用本文:曹霞,曾晞,牟兰,陈义,王瑞晓,张云黔,张建新,卫钢. 2[(N-乙基)-1-吩噻嗪基]腙的合成及聚集荧光增强性能[J]. 高等学校化学学报, 2012, 33(10): 2184-2190. DOI: 10.7503/cjcu20120082
作者姓名:曹霞  曾晞  牟兰  陈义  王瑞晓  张云黔  张建新  卫钢
作者单位: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
基金项目:国家自然科学基金,教育部"春晖计划"项目,贵州省国际合作项目基金,贵州大学研究生创新基金
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  
收稿时间:2012-01-19

Synthesis, Characterization and Aggregation Induced Enhanced Emission of New Phenothiazine Hydrazone
CAO Xia , ZENG Xi , MU Lan , CHEN Yi , WANG Rui-Xiao , ZHANG Yun-Qian , ZHANG Jian-Xin , WEI Gang. Synthesis, Characterization and Aggregation Induced Enhanced Emission of New Phenothiazine Hydrazone[J]. Chemical Research In Chinese Universities, 2012, 33(10): 2184-2190. DOI: 10.7503/cjcu20120082
Authors:CAO Xia    ZENG Xi    MU Lan    CHEN Yi    WANG Rui-Xiao    ZHANG Yun-Qian    ZHANG Jian-Xin    WEI Gang
Affiliation: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
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.
Keywords:N-ethyl)-1-phenothiazinyl]hydrazone')"   href="  #"  >2[(N-ethyl)-1-phenothiazinyl]hydrazone  Aggregation induced emission enhancement  Restriction of intramolecular rotation  Fluorescence probe
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