新型萘四酰亚胺类长波长荧光染料的构建及其光谱调控

doi:10.7517/j.issn.1674-0475.2011.05.344

影像科学与光化学 ›› 2011, Vol. 29 ›› Issue (5): 344-352.DOI: 10.7517/j.issn.1674-0475.2011.05.344

新型萘四酰亚胺类长波长荧光染料的构建及其光谱调控

陆欣宇¹, 刘宏伟², 朱为宏¹

1. 华东理工大学精细化工研究所结构可控先进功能材料及其制备教育部重点实验室, 上海200237;
2. 华东理工大学药学院, 上海200237

收稿日期:2011-04-25 修回日期:2011-05-25 出版日期:2011-09-23 发布日期:2011-09-23
通讯作者: 朱为宏,E-mail:whzhu@ecust.edu.cn;刘宏伟,E-mail:hwliu@ecust.edu.cn.
基金资助:
国家自然科学基金(61077085);高等学校博士学科点专项科研基金(SRFDP200802510011)

Synthesis and Optical Properties of Novel Long Wavelength Florescent Dyes Based on Naphthalene Diimide

LU Xin-yu¹, LIU Hong-wei², ZHU Wei-hong¹

1. Key Laboratory for Advanced Materials, Institute of Fine Chemicals, East China University of Science &Technology, Shanghai 200237, P. R. China;
2. School of Pharmacy, East China University of Science &Technology, Shanghai 200237, P. R. China

Received:2011-04-25 Revised:2011-05-25 Online:2011-09-23 Published:2011-09-23

摘要/Abstract

摘要： 本文通过杂环胺类对二溴萘四酰亚胺的亲核反应,分别设计合成了8个未见报道的基于萘四酰亚胺母体的新型单取代或者双取代荧光染料.系统性光谱研究表明,胺类的推电子作用差异可以很好地调控其吸收和荧光波长,使之成为一类性能良好的可见或长波长荧光染料(最大吸收509—580 nm;最大发射565—638 nm;荧光量子效率0.21—0.54;Stokes位移36—77 nm).

关键词: 萘四酰亚二胺, 合成, 荧光染料, 光谱调控

Abstract: Eight highly colored and photoluminescent mono-or di-core-substituted naphthalene diimide(NDIs) have been rationally designed and synthesized from 2,6-dibromonaphthalene diimide(DBI) via a stepwise nucleophilic substitution of two bromine atoms by heterocyclic secondary amine.Electronic absorption and fluorescence studies revealed that the amine substituents with different electron-donating abilities can lead to the NDIs with tunable absorption and emission properties,falling in the preferable region to long wavelength(λ_max^abs: 509—580 nm;λ_max^em: 565—638 nm;Φ_F: 0.21—0.54;Stokes shift: 36—77 nm).

Key words: naphthalene diimide, synthesis, fluorescent dyes, optical tuning

中图分类号:

陆欣宇, 刘宏伟, 朱为宏. 新型萘四酰亚胺类长波长荧光染料的构建及其光谱调控[J]. 影像科学与光化学, 2011, 29(5): 344-352.

LU Xin-yu, LIU Hong-wei, ZHU Wei-hong. Synthesis and Optical Properties of Novel Long Wavelength Florescent Dyes Based on Naphthalene Diimide[J]. Imaging Science and Photochemistry, 2011, 29(5): 344-352.

参考文献

[1] Würthner F,Ahmed S,Thalacker C,et al.Core substituted naphthalene bisimides:new fluorophors with tuna-ble emission wavelength for FRET studies[J].Chem.Eur.J.,2002,8(20):4742-4750.
[2] Yue W,Zhen Y,Li Y,et al.One-pot synthesis of well-defined oligo-butadiynylene-naphthalene diimides[J].Org.Lett.,2010,12(15):3460-3463.
[3] Guo X,Watson M D.Conjugated polymers from naphthalene bisimide[J].Org.Lett.,2008,10(23):5333-5336.
[4] Röger C,Würthner F.Core-tetrasubstituted naphthalene diimides:synthesis,optical properties,and redoxcharacteristics[J].J.Org.Chem.,2007,72(21):8070-8075.
[5] Blaszczyk A,Fischer M,von Hänisch C,et al.Synthesis,structure,and optical properties of terminally sulfur-functionalized core-substituted naphthalene-bisimide dyes[J].Helv.Chim.Acta.,2006,89(9):1986-2005.
[6] Thalacker C,Röger C,Würthner F.Synthesis and optical and redox properties of core-substituted naphthalenediimide dyes[J].J.Org.Chem.,2006,71(21):8098-8105.
[7] Vollmann H,Becker H,Corell M,et al.Beiträge zur kenntnis des pyrens und seiner derivate[J].LiebigsAnn.,1937,531(1):1-159.
[8] Chopin S,Chaignon F,Blart E,et al.Syntheses and properties of core-substituted naphthalene bisimides witharyl ethynyl or cyano groups[J].J.Mater.Chem.,2007,17(42):4139-4146.
[9] Krüger H,Janietz S,Sainova D,et al.Hybrid supramolecular naphthalene diimide-thiophene structures andtheir application in polymer electronics[J].Adv.Funct.Mater.,2007,17(18):3715-3723.
[10] Sakai N,Mareda J,Vauthey E,et al.Core-substituted naphthalenediimides[J].Chem.Commun.,2010,46(24):4225-4237.
[11] Lu X,Zhu W,Xie Y,et al.Near-IR core-substituted naphthalenediimide fluorescent chemosensors for zinc i-ons:ligand effects on PET and ICT channels[J].Chem.Eur.J.,2010,16(28):8355-8364.
[12] de Silva A,Gunaratne H,Habib-Jiwan J,et al.New fluorescent model compounds for the study of photoin-duced electron transfer:the influence of a molecular electric field in the excited state[J].Angew.Chem.,Int.Ed.,1995,34(16):1728-1731.
[13] Hurenkamp J H,Browne W R,Augulis R,et al.Intramolecular energy transfer in a tetra-coumarin perylenesystem:influence of solvent and bridging unit on electronic properties[J].Org.Biomol.Chem.,2007,5(20):3354-3362.
[14] Würthner F,Wortmann R,Matschiner R,et al.Merocyanine dyes in the cyanine limit:a new class of chro-mophores for photorefractive materials[J].Angew.Chem.,Int.Ed.,1997,36(24):2865-2768.

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新型萘四酰亚胺类长波长荧光染料的构建及其光谱调控

Synthesis and Optical Properties of Novel Long Wavelength Florescent Dyes Based on Naphthalene Diimide

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