Preparation and Optical Properties of Coumarin Fluorescent Polymer

WANG Peng; ZHANG Guang-hua; XIANG Rui

doi:10.3788/fgxb20133410.1313

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Preparation and Optical Properties of Coumarin Fluorescent Polymer

更新时间：2020-08-12

- Preparation and Optical Properties of Coumarin Fluorescent Polymer
- Chinese Journal of Luminescence Vol. 34, Issue 10, Pages: 1313-1318(2013)
- 作者机构：
  
  陕西科技大学教育部轻化工助剂化学与技术重点实验室,陕西西安,710021
- 作者简介：
- 基金信息：
- DOI：10.3788/fgxb20133410.1313
  CLC： TQ610.4+95
- Received：20 May 2013，
  
  Revised：04 July 2013，
  
  Published：10 October 2013
- 稿件说明：
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王鹏, 张光华, 相瑞. 香豆素型荧光聚合物的合成及光学性能[J]. 发光学报, 2013,34(10): 1313-1318

WANG Peng, ZHANG Guang-hua, XIANG Rui. Preparation and Optical Properties of Coumarin Fluorescent Polymer[J]. Chinese Journal of Luminescence, 2013,34(10): 1313-1318
王鹏, 张光华, 相瑞. 香豆素型荧光聚合物的合成及光学性能[J]. 发光学报, 2013,34(10): 1313-1318 DOI： 10.3788/fgxb20133410.1313.

WANG Peng, ZHANG Guang-hua, XIANG Rui. Preparation and Optical Properties of Coumarin Fluorescent Polymer[J]. Chinese Journal of Luminescence, 2013,34(10): 1313-1318 DOI： 10.3788/fgxb20133410.1313.

摘要

以对甲苯磺酸为催化剂

通过Pechmann法使间苯二酚和乙酰乙酸乙酯发生脱水缩合反应

合成了7-羟基-4-甲基香豆素

再以三聚氯氰为交联单体

将7-羟基-4-甲基香豆素和紫外线吸收剂2

4-二羟基-二苯甲酮引入同一分子中

并使其与丙烯酰胺按一定比例聚合

得到一种能溶于水的荧光聚合物。通过红外光谱和核磁氢谱对产物进行结构表征

运用紫外光谱、荧光光谱测试其光学特性

并考察其在纸张上的应用效果。结果表明:荧光聚合物的Stokes位移(3 121.2 cm

-1

)比单体(5 221.5 cm

-1

)小

空间位置变化小

损失能量低

说明其结构更稳定

光稳定性更好

应用于纸张的抗紫外光老化效果也更优。

Abstract

Employing toluene-p-sulfonic acid as the activator

7-hydroxy-4-methyl coumarin was synthesized by dehydration condensation reaction of resorcinol and ethyl acetoacetate through the Pechmann method. Cyanuric chloride was used as the crosslinking monomer

a water-soluble fluorescent polymer was prepared through joining the 7-hydroxy-4-methyl coumarin

ultraviolet absorber 2

4-dihydroxy-benzophenone and a certain percentage of acrylamide. The molecular structures were characterized by IR spectra and

H NMR

and the optical properties were measured by UV spectra and fluorescence spectra. The application effect of the polymer in paper sheet was tested. The results show that the Stokes shift of polymer(3 121.2 cm

-1

) is less than monomer(5 221.5 cm

-1

)

the polymer steric resistance change is smaller

and the energy loss is less. These indicate that the polymer owns a more stable structure

a better light stability

and a better effect in UV ageing resistance on paper sheet than fluorescent monomer.

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Keywords

references

Guo Y, Song D M, Wei Y F, et al. Efficient synthesis and fluorescence properties of novel coumarins [J]. Chin. J. Appl. Chem.(应用化学), 2009, 26(6):681-685 (in Chinese).[2] Liu X G, Cole J M, Waddell P G, et al. Molecular origins of optoelectronic properties in coumarin dyes: Toward designer solar cell and laser applications [J]. J. Phys. Chem. A, 2012, 116(1):727-737.[3] Sednev M V, Wurm C A, Belov V N, et al. Carborhodol: A new hybrid fluorophore obtained by combination of fluorescein and carbopyronine dye cores [J]. Bioconjugate Chem., 2013, 24(4):690-700.[4] Simmons J T, Allen J R, Morris D R, et al. Integrated and passive 1,2,3-triazolyl groups in fluorescent indicators for zinc(Ⅱ) ions: Thermodynamic and kinetic evaluations [J]. Inorg. Chem. A, 2013, 52(10):5838-5850.[5] Zhang G H, Guo J G, Xu H L, et al. Synthesis and application of yellowing inhibitor based on naphthalimide fluorescent brightening agent [J]. Transactions of China Pulp and Paper (中国造纸学报), 2012, 27(2):29-34 (in Chinese).[6] Zhang G H, Xu H L, Guo J G, et al. Synthesis and properties of new yellowing inhibitor with fluorescent whitening [J]. J. Chem. Ind. Eng.(化工学报), 2012, 63(10):3358-3364.[7] Zhang Y H, Zhang Q P, Shi W Y, et al. Synthesis and quantum chemistry study on fluorescence spectra of three 1,8-naphthalimide monomers [J]. Chin. J. Lumin.(发光学报), 2011, 32(5):505-513 (in Chinese).[8] Chen J, He Y, Pan Z D, et al. Synthesis and optoelectronic properties of aromatic polyethers with a 1,8-naphthalimide unit main chain [J]. Chin. J. Lumin.(发光学报), 2012, 33(3):243-246 (in Chinese).[9] Guo J G, Zhang G H, Xu H L, et al. Synthesis and application of polymeric yellowing inhibitor based on naphthalimide fluorescent brightening agent [J]. J. Funct. Mater.(功能材料), 2012, 43(23):2881-2885 (in Chinese).[10] Liu L J, Zhang G H. Preparation and properties of polymerizable fluorescent materials[J]. Polymer Mater. Sci. Eng.(高分子材料科学与工程), 2011, 27(12):4-8 (in Chinese).[11] Cao C B, Han H B, Wang D Y, et al. Synthesis and properties of quaternary ammonium salt fluorescent brighteners [J]. J. Chem. Ind. Eng.(化工学报), 2006, 57(12):3010-3015 (in Chinese).[12] Wei Y J, Li N, Qin S J. Fluorescence spectra and fluorescence quantum yield of sulfo salicylic acid [J]. Spectrosc. Spect. Anal.(光谱学与光谱分析), 2004, 24(6):647-651 (in Chinese).[13] Zhang H J, Hu H R, He Z B. Using fluorescent whitening agent to improve optical properties of high yield pulp [J].China Pulp and Paper (中国造纸), 2010(9):1-6 (in Chinese).[14] Zhang R. Synthesis of A Novel Yellowing Inhibitor and Study of Its Use for High-yield Bamboo Pulps. Nanning: Guangxi University, 2008 (in Chinese).

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