光谱学与光谱分析, 2009, 29 (10): 2810, 网络出版: 2010-08-31  

新型吡唑啉类荧光化合物的合成及光谱分析

Synthesis and Spectrum of Novel Pyrazoline Fluorescent Compounds
作者单位
1 长春工业大学化学与生命科学学院, 吉林 长春 130012
2 长春应用化学研究所高分子物理与化学国家重点实验室, 吉林 长春 130022
摘要
吡唑啉衍生物作为荧光增白剂具有优良的性质,已被广泛应用于染料工业。根据Schellhammer化学结构与荧光性的经验,在吡唑啉环的1-位引入苯并噻唑基,3-位引入吲哚基,5-位引入苯基衍生物,设计并合成了六种新的吡唑啉衍生物,并且通过红外光谱、^1H NMR谱、质谱和元素分析进行了确证。化合物的荧光性能测定结果显示此类化合物具有良好的荧光性,均可吸收353nm左右紫外光,最大发射波长在430~443nm之间,是一类很有发展前途的蓝紫色荧光化合物。荧光最大发射波长和荧光强度与取代基有关,在苯并噻唑上引入6-Br基团,化合物的荧光发射波长发生蓝移,且强度增大;而引入CH3基团,化合物的荧光发射波长发生红移,且强度降低。取代基和溶剂极性对荧光量子产率的影响较小。荧光相对强度与荧光量子产率没有直接关系。
Abstract
Pyrazoline derivatives have been used widely in dyeing industry as fluorescent whitening agents due to their excellent capability. According to Schellhammer theory of the relation between chemical structure and fluorescent quality, six new fluorescent compounds were designed and synthesized which contained the benzothiazole group in the 1-pyrazoline, the indole group in the 3-pyrazoline and the derivatives of phenyl in the 5-pyrazoline. The structure of target compounds was confirmed by IR, ^1H NMR, MS and elementary analysis. The fluorescence spectra showed that these compounds had good fluorescence. They could absorb ultraviolet light at near 353 nm. The fluorescence maximum emission wavelengths were about 430-443 nm. It was a kind of promising fluorescence compounds. The largest fluorescence emission wavelength and the fluorescence intensity were related to the substituted group of the compounds. When the 6-Br group was introduced into benzothiazole, the fluorescence emission wavelength exhibited a blue shift, and the fluorescence intensity increased. Otherwise, the CH3 group was introduced to benzothiazole, the fluorescence emission wavelength red-shift occurred, and the intensity was lower. The fluorescence quantum yield of the compounds was little affected by the substituted group and polarity of the solvent. The relative fluorescence intensity and fluorescence quantum yield were not directly related.

刘秋君, 高磊, 王雷, 谢志元, 李东风. 新型吡唑啉类荧光化合物的合成及光谱分析[J]. 光谱学与光谱分析, 2009, 29(10): 2810. LIU Qiu-jun, GAO Lei, WANG Lei, XIE Zhi-yuan, LI Dong-feng. Synthesis and Spectrum of Novel Pyrazoline Fluorescent Compounds[J]. Spectroscopy and Spectral Analysis, 2009, 29(10): 2810.

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