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Citation: ZHOU Qiuxuan, GU Peiyang, LU Jianmei, XU Qingfeng, ZHANG Yong. Synthesis and Fluorescence of a New pH-Sensitive Pyran Nitrile Derivatives[J]. Chinese Journal of Applied Chemistry, ;2013, 30(5): 506-510. doi: 10.3724/SP.J.1095.2013.20288 shu

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

a. Analysis and Testing Center of Soochow University, Suzhou 215123, China;
b. The Testing and Technical Service Center of Jiangsu Province for Energy-saving and Environment-friendly Materials, Suzhou 215123, China

Received Date: 2 July 2012
Revised Date: 31 October 2012

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.
- DCM,
- fluorescence,
- concentration quenching effect,
- solvent effect,
- pH influence
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