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
展开
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

收稿日期: 2015-09-12

  网络出版日期: 2016-03-25

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

Received date: 2015-09-12

  Online published: 2016-03-25

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.

本文引用格式

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 . DOI: 10.3969/j.issn.1000-1565.2016.02.005

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.

参考文献

[1] WÜRTHNER F.Perylene bisimide dyes as versatile building blocks for functional supramolecular architectures[J].Chemical Communications,2004,35(14):1564-1579.DOI:10.1039/B401630K.
[2] LANGHLS H.Cyclic carboxylic imide structures as structure elements of high stability.Novel developments in perylene dye chemistry[J].Heterocycles,1995,1(40):477-500.DOI:10.3987/REV-94-SR2.
[3] SCHLETTWEIN D,WÖHRLE D,KARMANN E,et al.Conduction type of substituted tetraazaporphyrins and perylene tetracarboxylic acid diimides as detected by thermoelectric power measurements[J].Chemistry of Materials,1994,6(1):3-6.DOI:10.1021/cm00037a001.
[4] SCHNEIDER M,HAGEN J,HAARER D,et al.Novel electroluminescent devices based on perylene-doped sol-gel layers[J].Advanced Materials,2000,12(5):351-354.DOI:10.1002/(SICI)1521-4095(200003)12:5<351:AID-ADMA351>3.0.CO;2-X.
[5] LI Y,TAN L,WANG Z,et al.Air-stable n-type semiconductor:Core-perfluoroalkylated perylene bisimides[J].Organic Letters,2008,10(4):529-532.DOI:10.1021/ol703046w.
[6] HUNGER K.Industrial organic pigments:production,properties,applications[M].Weinheim:Wiley-Vch,1997.
[7] GRIMSDALE A C,MÜLLEN K.The chemistry of organic nanomaterials[J].Angewandte Chemie International Edition,2005,44(35):5592-5629.DOI:10.1002/anie.200500805.
[8] WICKLEIN A,LANG A,MUTH M,et al.Swallow-tail substituted liquid crystalline perylene bisimides:synthesis and thermotropic properties[J].Journal of the American Chemical Society,2009,131(40):14442-14453.DOI:10.1021/ja905260c.
[9] ZHANG X,CHEN Z,WÜRTHNER F.Morphology control of fluorescent nanoaggregates by co-self-assembly of wedge-and dumbbell-shaped amphiphilic perylene bisimides[J].Journal of the American Chemical Society,2007,129(16):4886-4887.DOI:10.1021/ja070994u.
[10] ZHAO Y,WASIELEWSKI M R.3,4:9,10-Perylenebis(dicarboximide)chromophores that function as both electron donors and acceptors[J].Tetrahedron Letters,1999,40(39):7047-7050.DOI:10.1016/S0040-4039(99)01468-9.
[11] JIMÉNEZ Á J,SPÄNIG F,RODRíGUEZ-MORGADE M S,et al.A tightly coupled bis(zinc(Ⅱ)phthalocyanine)-perylenediimide ensemble to yield long-lived radical ion pair states[J].Organic Letters,2007,9(13):2481-2484.DOI:10.1021/ol0707968.
[12] SCHNURPFEIL G,STARK J,WÖHRLE D.Syntheses of uncharged,positively and negatively charged 3,4,9,10-perylene-bis(dicarboximides)[J].Dyes and Pigments,1995,27(4):339-350.DOI:10.1016/0143-7208(94)00075-D.
[13] DUAN W,WEI H,CUI T,et al.A membrane permeable fluorescent Ca2+ probe based on bis-BODIPY with branched PEG[J].Journal of Materials Chemistry B,2015,3(5):894-898.DOI:10.1039/C4TB01457J.
[14] WU X,YIN C,SHI Z,et al.A novel substitution reaction of perylene bisimides with Ph2PLi at the α-position[J].New Journal of Chemistry,2010,34(1):61-64.DOI:10.1039/B9NJ00364A.
文章导航

/

〈 〉