2[(N-乙基)-1-吩噻嗪基]腙的合成及聚集荧光增强性能

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

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。

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 enhance- ment.