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

doi:10.7503/cjcu20120082

Chem. J. Chinese Universities ›› 2012, Vol. 33 ›› Issue (10): 2184.doi: 10.7503/cjcu20120082

• Analytical Chemistry • Previous Articles Next Articles

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. 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

Abstract

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

CLC Number:

O657

TrendMD:

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]. Chem. J. Chinese Universities, 2012, 33(10): 2184.

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

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