Synthesis and Quantum Chemistry Study on Fluorescence Spectra of Three 1,8-naphthalimide Monomers

ZHANG Yue-hua; ZHANG Qi-ping; SHI Wen-yan; LEI Wu; XIA Ming-zhu; WANG Feng-yun

doi:10.3788/fgxb20113205.0505

您当前的位置：

首页 >

文章列表页 >

Synthesis and Quantum Chemistry Study on Fluorescence Spectra of Three 1,8-naphthalimide Monomers

paper | 更新时间：2020-08-12

- Synthesis and Quantum Chemistry Study on Fluorescence Spectra of Three 1,8-naphthalimide Monomers
- Chinese Journal of Luminescence Vol. 32, Issue 5, Pages: 505-513(2011)
- 作者机构：
  
  1. 盐城工学院化学与生物工程学院,江苏盐城,224051
  2. 南京理工大学工业化学研究所,江苏南京,210094
  3. 南通大学化学化工学院,江苏南通,226007
- 作者简介：
- 基金信息：
- DOI：10.3788/fgxb20113205.0505
  CLC： TQ617.3;O482.31
- Received：13 September 2010，
  
  Revised：03 November 2010，
  
  Published Online：22 May 2011，
  
  Published：22 May 2011
- 稿件说明：
移动端阅览
张跃华, 张其平, 石文艳, 雷武, 夏明珠, 王风云. 1,8-萘酰亚胺荧光单体的合成及光谱的量子化学研究[J]. 发光学报, 2011,32(5): 505-513

ZHANG Yue-hua, ZHANG Qi-ping, SHI Wen-yan, LEI Wu, XIA Ming-zhu, WANG Feng-yun. Synthesis and Quantum Chemistry Study on Fluorescence Spectra of Three 1,8-naphthalimide Monomers[J]. Chinese Journal of Luminescence, 2011,32(5): 505-513
张跃华, 张其平, 石文艳, 雷武, 夏明珠, 王风云. 1,8-萘酰亚胺荧光单体的合成及光谱的量子化学研究[J]. 发光学报, 2011,32(5): 505-513 DOI： 10.3788/fgxb20113205.0505.

ZHANG Yue-hua, ZHANG Qi-ping, SHI Wen-yan, LEI Wu, XIA Ming-zhu, WANG Feng-yun. Synthesis and Quantum Chemistry Study on Fluorescence Spectra of Three 1,8-naphthalimide Monomers[J]. Chinese Journal of Luminescence, 2011,32(5): 505-513 DOI： 10.3788/fgxb20113205.0505.

摘要

以4-溴-1

8-萘二甲酸酐和N-甲基哌嗪为原料

合成了3种水溶性1

8-萘酰亚胺荧光单体

并以红外光谱、氢核磁共振谱、质谱及元素分析对产物进行了表征

测定了它们的激发光谱和发射光谱。运用PM3方法对这3种化合物的基态和激发态进行了几何构型全优化。结构分析表明:基态下

3种荧光单体的环均处于同一平面

且体系为较大的共轭体系。振动分析表明

上述优化构型均为稳定结构。在此基础上

应用含时密度泛函理论(TD-DFT)

在B3LYP/6-31G

水平下分别计算了该3种单体的激发和发射光谱。预测的光谱性质与实验结果符合得较好。

Abstract

Three water soluble 1

8-naphthaline fluorescent monomers were synthesized by using 4-bromo-1

8-naphthalic anhydride and N-methyl-piperazine. The structures were characterized by IR

H NMR and element analysis. The fluorescent excitation and emission spectra were investigated. The structures of the three flourescent monomers were optimized in the ground and the first excited state by PM3 method. The analysis of structure indicates that the rings in the three fluorescent monomers are in the same plane

and the conjugate system is formed. For all the optimal configurations

there is no imaginary frequency after vibrational analysis

which indicates that the structures are true local minima. On the basis of optimized structures for both the ground state and the first excited state

the time dependent density function theory(TD-DFT)at the B3LYP/6-31G

level was used to predict the absorption and emission wavelength.The results indicate that the wavelength of the excitation and emission spectra are well consistent with the experimental data.

关键词

Keywords

references

Wu Hongmei, Zhou Peng, Zhao Liang, et al. Selective detection of Zn2+ ion based on quinoline fluorophore [J]. Chin. J. Lumin.(发光学报), 2008, 29 (6):1091-1095 (in Chinese).[2] Fu Meiyan, Xiao Yi. The synthesis and application of a new thiocyanate sensor based on naphthalimide [J]. Chin. J. Lumin.(发光学报), 2009, 30 (4):482-486 (in Chinese).[3] Wang Fuqiang, Li Yaming, Liu Jun, et al. Synthesis of distyrylbenzene based fluorescent probes and their recognition of metal ions [J]. Acta Chimica Sinica (化学学报), 2008, 66 (1):103-107 (in Chinese).[4] Robson V P, Ana P G F, Marcelo H G. Fluorescent probes with malononitrile side group in methyl methacrylate copolymers [J]. Journal of Photochemistry and Photobiology A: Chemistry, 2008, 198 (1):69-74.[5] Zhao Huihui, Hou Na, Wang Wei. Difference expressed protein study on unstable angina blood-stasis syndrome by fluorescence labelling method [J]. Spectroscopy and Spectral Analysis (光谱学与光谱分析), 2009, 29 (6):1647-1650 (in Chinese).[6] Li Peng, Wang Jing, Gao Yunhua, et al. Analysis of fluorescent dye-labeled oligonucleotides by ion pair reversed phase high performance liquid chromatography [J]. Analytical Chemistry (分析化学), 2009, 37 (12):1722-1726 (in Chinese).[7] Zhang Mingzhen, Duhamel J. Study of maleated ethylene-propylene copolymers by fluorescence:Evidence for succinimide induced polar associations in an apolar solvent [J]. European Polymer Journal, 2008, 44 (9):3005-3014.[8] Morris J D, Moriarty B E. Fluorescent monomers and tagged treatment polymers containing same for use in industrial water systems:WO,01/81 654 Al . 2001-11-01.[9] Lei Wu, Zhang Yuehua, Xia Mingzhu, et al. Preparation and performance of the phosphono-based maleic anhydride/acrylic acid copolymer containing fluorescent group [J]. Fine Chem. (精细化工), 2006, 23 (7):687-691 (in Chinese).[10] Lei Wu, Ping Chunxia, Wang Fenghe, et al. Synthesis of acrylic acid-acrylamide copolymer containing fluorescent group [J]. Petrochem. Equip. (石油化工), 2006, 35 (2):145-150 (in Chinese).[11] Zhang Yuehua, Xia Mingzhu, Lei Wu, et al. Study on the performance of traced maleic anhydride-acrylic acid copolymers [J]. Ind. Water Treat. (工业水处理), 2006, 26 (5):27-28,37 (in Chinese).[12] Lei Wu, Zhang Yuehua, Zhu Jiang, et al. Preparation and performance of 2-acrylamido-2-methyl-propanesulfonic acid/acrylic acid copolymer containing fluorescent group [J]. J. Chem. Ind. Eng. (化工学报), 2008, 59 (2):520-525 (in Chinese).[13] Zhang Yuehua, Xia Mingzhu, Lei Wu, et al. Synthesis and optical properties of 4-methoxy-N-(2-N',N'-dimethylaminoethyl)naphthalimide allyl chloride quaternary ammonium salt [J]. Chin. J. Appl. Chem. (应用化学), 2005, 22 (10):1145-1148 (in Chinese).[14] Zhang Qiping, Zhang Yuehua, Huang Dan. Synthesis and characterization of water-soluble fluorescent monomer based on 1, 8-naphthalimide [J]. Chem. Reag. (化学试剂), 2007, 29 (2):78-80 (in Chinese).[15] Zhang Mian, Cui Jingnan. Synthesis of water-soluble fluorescent dyes based on 1,8-naphthalic anhydride [J]. Fine Chem. (精细化工), 2004, 21 (10):782-784 (in Chinese).[16] Zhang Yuehua, Zhang Qiping, Lei Wu, et al. Synthesis, characterization and properties of 1,8-naphthalimide fluorescent monomer [J]. Speciality petrochemicals (精细石油化工), 2008, 25 (5):60-64 (in Chinese).[17] Frisch M J, Trucks G W, Schlegel H B, et al. Gaussian 98 . Revision A.7, Gaussian Inc., Pittsburgh PA:1998.[18] Casida M E, Jamorski C, Casida K C, et al. Molecular excitation energies to high-lying bound states from time dependent density- functional response theory: Characterization and correction of the time-dependent local density approximation ionization threshold [J]. Journal of Chemical Physics, 1998, 108 (11):4439-4449.[19] Su Yu, Liu Shan, Yang Ming, et al. Quantum chemistry study on fluorescence spectra of four polycyclic aromatic hydrocarbons [J]. Chin. J. Lumin.(发光学报), 2006, 27 (3):363-366 (in Chinese).[20] Hehre W J, Pople J A. Ab Initio Molecular Orbital Theory [M]. New York: John Wiley & Sons, 1985:277.[21] Li Zhenyu, He Wei, Yang Jinlong. Recent progress in density functional theory and its numerical methods [J]. Progress in Chemistry (化学进展), 2005, 17 (2):192-202 (in Chinese).

Views

295

下载量

CSCD

Alert me when the article has been cited

提交

Tools

Publicity Resources

Multiple Peak Calibration of Gasoline-in-water Concentration Measurement Using Three-dimensional Fluorescence Spectra

Effect of Excitation Wavelength and Bandwidth on Luminescent Properties of Ce/Tb/Eu Co-doped Luminescence Glass

Quantum Chemical Study on The Fluorescence Spectroscopy of Three Kinds of 1,4-Phthalaldehyde Schiff Base Molecule

Study of Absorption and Fluorescence Spectra of Two Organophosphate Pesticides

Quantum Chemistry Study on Fluorescence Spectra of Four Polycyclic Aromatic Hydrocarbons

Related Author

ZHANG Jing-chao

XIAO Chang-jiang

JIN Lei

FENG Yong-an

DU Xiao-qing

CHEN Wei-min

LEI Xiao-hua

REN Lin-jiao

Related Institution

College of Science, Yanshan University

Liren College, Yanshan University

重庆大学光电工程学院光电技术与系统教育部重点实验室

College of Chemical and Biological Engineering Guilin University of Technology

School of Science, Jiangnan University

AI问答

Address：No.3888 Dong Nanhu Road, Changchun, Jilin, China Postal code：130033
Tel：0431-86176862 Email：fgxbt@126.com
Technical support is provided by Beijing Founder electronics co., LTD 吉ICP备11002662号-17 京公网安备11010802024621
It is recommended to read the content of this site in Chrome&IE9+. Please switch to extreme mode in browser 360.
Cookies We use cookies to help provide and enhance our service and tailor content. By continuing, you agree to the use of cookies.

⁰