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

doi:10.7517/j.issn.1674-0475.2011.05.344

Abstract

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

CLC Number:

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.

References

[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.

[1]	ZHU Tao, ZHANG Yan, DONG Lulu, GUO Pengyue, YANG Dongzhi. Biomimetic Synthesis of Au QDs and the Application of Glucose Detection in Serum [J]. Imaging Science and Photochemistry, 2020, 38(6): 941-949.
[2]	TAO Pingfang, FENG Yuqin, ZHOU Neng, QIN Liqin, ZHANG Pei. Hydrothermal Synthesis of α-NaYF₄: Ce³⁺/Tb³⁺ Nanospheres with High Fluorescence Properties [J]. Imaging Science and Photochemistry, 2018, 36(2): 161-170.
[3]	JI Haixia, DONG Lulu, DU Yan, YAO Xinyue, YANG Dongzhi. Biomimetic Synthesis of CdS Quantum Dots in Living Cancer Cells [J]. Imaging Science and Photochemistry, 2018, 36(1): 57-63.
[4]	ZENG Ze, ZHONG Rong, ZHANG Chunhui, XIE Gang. Synthesis and Properties of Phenylglyoxylic Acid Ester/2959 Photoinitiator [J]. Imaging Science and Photochemistry, 2017, 35(6): 808-815.
[5]	DENG Yafeng, ZHOU Yihua, QIAN Jun, LUO Yan, WU Lihui. Preparation and Application of Carbon Quantum Dots Based on Up Conversion Photoluminescence [J]. Imaging Science and Photochemistry, 2017, 35(6): 884-893.
[6]	WANG Hua. Chemical and Photochemical Synthesis of Thiophene-based Helicenes [J]. Imaging Science and Photochemistry, 2017, 35(5): 603-613.
[7]	ZHANG Qingbao, LIU Qiang. Applications of Visible-light-driven Aerobic Oxidation in Organic Synthesis [J]. Imaging Science and Photochemistry, 2017, 35(5): 614-625.
[8]	CAO Yitao, WU Lizhu, TONG Zhenhe(TUNG Chenho), ZHANG Tierui. Photochemical Synthesis of Inorganic Nanomaterials [J]. Imaging Science and Photochemistry, 2017, 35(5): 642-648.
[9]	GUI Mengxi, YU Yang, ZHU Chengyi, LIU Hongfang, WANG Feng. Advances on Molecular Systems for Photocatalytic CO₂ Reduction Based on Cobalt Complexes as Catalysts [J]. Imaging Science and Photochemistry, 2017, 35(5): 649-657.
[10]	LEI Yuan, ZHANG Sai, GAO Jun. Synthesis,Structure and Photochromic Properties of N-ethyl-9'-n Bromobutoxy Spirooxazine and Its Modified PMMA [J]. Imaging Science and Photochemistry, 2016, 34(6): 526-533.
[11]	JIANG Wei, WU Xiang. Hydrothermal Synthesis and Photocatalytic Properties of ZnS Microflowers [J]. Imaging Science and Photochemistry, 2016, 34(3): 252-256.
[12]	YANG Ke, ZHANG Yan, XU Jianhua. The Application of Electron Transfer Photo-oxidation Reaction in Organic Synthesis [J]. Imaging Science and Photochemistry, 2014, 32(5): 433-446.
[13]	LI Bing, XIA Wujiong. Solid-state Asymmetric Photochemistry of Bicyclo[3.1.0] hexyl Ketone Carbonyl Derivatives [J]. Imaging Science and Photochemistry, 2014, 32(5): 455-462.
[14]	LIANG Qinghua, SHI Yao, MA Wangjing, YANG Xinmin, LI Zhi. Hydrothermal Synthesis and Characterization of Ba₇F₁₂Cl₂：Eu²⁺ Used for X-ray Imaging Plate [J]. Imaging Science and Photochemistry, 2014, 32(2): 150-156.
[15]	LI Bo, HUANG Zhongbing, MENG Xianwei, TANG Fangqiong. Hydrothermal Synthesis and Application of the Fe₃O₄ Nanoparticles Modified with L-cysteine [J]. Imaging Science and Photochemistry, 2014, 32(2): 163-170.