水溶性苝酰亚胺功能荧光染料的合成与性质

doi:10.3969/j.issn.1000-1565.2016.02.005

河北大学学报(自然科学版) ›› 2016, Vol. 36 ›› Issue (2): 134-140.DOI: 10.3969/j.issn.1000-1565.2016.02.005

水溶性苝酰亚胺功能荧光染料的合成与性质

高微,席亚楠,薄福丽,杨涛,高保祥

收稿日期:2015-09-12 出版日期:2016-03-25 发布日期:2016-03-25
通讯作者: 高保祥(1974—),男,河北滦县人,河北大学教授,博士生导师,主要从事功能性荧光染料的设计合成与荧光分子成像研究.E-mail:bxgao@hbu.edu.cn
作者简介:高微(1990—),女,河北保定人,河北大学在读硕士研究生. E-mail:15733205590@163.com
基金资助:
国家自然科学基金资助项目(21274036);河北省高层次人才项目(B2012201031)

Synthesis and characterization of water-soluble fluorescent perylene bisimides

GAO Wei,XI Ya'nan,BO Fuli,YANG Tao,GAO Baoxiang

Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of Ministry of Education, College of Chemistry and Environmental Science, Hebei University, Baoding 071002, China

Received:2015-09-12 Online:2016-03-25 Published:2016-03-25

摘要/Abstract

摘要： 通过在苝酰亚胺染料的亚胺位置引入寡聚乙二醇亲水功能基团,同时在苝酰亚胺染料的海湾位置引入硫醚取代基团,合成了水溶性苝酰亚胺功能荧光染料(PSPBI),其化学结构通过核磁共振波谱仪(NMR)、基质辅助激光解析电离飞行时间质谱(MALDI-TOF-MS)得以证实.溶解性实验表明PSPBI在水中的溶解度大于10 mg/mL,说明其具有很好的水溶性.紫外吸收与荧光发射测试表明:PSPBI在480 nm和540 nm有2个吸收峰;荧光发射峰在620 nm.过氧化氢荧光滴定实验结果表明:PSPBI能够实现对过氧化氢的荧光增强响应,增强倍率为50倍;同时,其吸收光谱和荧光发射光谱都发生了蓝移,最大吸收峰蓝移了29 nm,最大发射峰蓝移了15 nm.

关键词: 苝酰亚胺, 荧光性质, 过氧化氢, 分子内电荷转移, 功能染料

Abstract: Functional dye(PSPBI)was synthesized by the attachment of PEG and thioanisole groups to the imides and the bay of perylene bisimides,respectively.PSPBI dye was fully characterized by ¹H NMR spectroscopy,¹³C NMR spectroscopy and matrix-assisted laser desorption/ionization mass spectrometry.The solubility of PSPBI dye in water is more than 10 mg/mL,indicating good water solubility.In aqueous solution,the absorption maximum of PSPBI dye appeared at 540 nm,along with two higher vibronic transitions located at 480 nm,and the emission peak located at 620 nm.When the concentration of hydrogen peroxide was increased,the absorption maximum and emission peak were blue-shifted by 29 nm and 15 nm,respectively.Furthermore,PSPBI dye showed a fluorescence increase of about 50 fold.

Key words: perylene bisimides, fluorescence property, hydrogen peroxide, intramolecular charge transfer, functional dyes

中图分类号:

O625.6

高微,席亚楠,薄福丽,杨涛,高保祥. 水溶性苝酰亚胺功能荧光染料的合成与性质[J]. 河北大学学报(自然科学版), 2016, 36(2): 134-140.

GAO Wei,XI Ya'nan,BO Fuli,YANG Tao,GAO Baoxiang. Synthesis and characterization of water-soluble fluorescent perylene bisimides[J]. Journal of Hebei University (Natural Science Edition), 2016, 36(2): 134-140.

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水溶性苝酰亚胺功能荧光染料的合成与性质

Synthesis and characterization of water-soluble fluorescent perylene bisimides

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