含大体积侧基纤维素类衍生物的合成及其金属离子荧光识别性能研究

王宇清; 王凡; 代枭; 王伟琪; 沈军

doi:10.11777/j.issn1000-3304.2024.24055

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含大体积侧基纤维素类衍生物的合成及其金属离子荧光识别性能研究

研究论文 | 更新时间：2024-11-15

- 含大体积侧基纤维素类衍生物的合成及其金属离子荧光识别性能研究
- Synthesis of Cellulose Derivative Bearing Bulky Substituents and Fluorescence Recognition Property for Metal Ions
- 高分子学报 2024年55卷第10期页码：1335-1345
- 作者机构：
  
  1.哈尔滨工程大学材料科学与化学工程学院哈尔滨 150001
  2.铜陵学院机械工程学院铜陵 244000
  3.北京科技大学土木与资源工程学院北京 100083
- 作者简介：
  
  E-mail: wangfan@hrbeu.edu.cn
  shenjun@hrbeu.edu.cn
- 基金信息：
  
  国家自然科学基金(基金号 ┣51673052;21474024);51073046┫;黑龙江省自然科学基金重点项目(基金号 ZD2021B001);黑龙江省自然科学基金联合引导项目(基金号 LH2023E063);铜陵学院人才科研启动基金(基金号 2023tlxyrc23)
- DOI：10.11777/j.issn1000-3304.2024.24055
  中图分类号：
- 纸质出版日期：2024-10-20，
  
  网络出版日期：2024-05-23，
  
  收稿日期：2024-02-23，
  
  录用日期：2024-04-12
- 稿件说明：
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王宇清, 王凡, 代枭, 王伟琪, 沈军. 含大体积侧基纤维素类衍生物的合成及其金属离子荧光识别性能研究. 高分子学报, 2024, 55(10), 1335-1345

Wang, Y. Q.; Wang, F.; Dai, X.; Wang, W. Q.; Shen, J. Synthesis of cellulose derivative bearing bulky substituents and fluorescence recognition property for metal ions. Acta Polymerica Sinica, 2024, 55(10), 1335-1345
王宇清, 王凡, 代枭, 王伟琪, 沈军. 含大体积侧基纤维素类衍生物的合成及其金属离子荧光识别性能研究. 高分子学报, 2024, 55(10), 1335-1345 DOI： 10.11777/j.issn1000-3304.2024.24055.

Wang, Y. Q.; Wang, F.; Dai, X.; Wang, W. Q.; Shen, J. Synthesis of cellulose derivative bearing bulky substituents and fluorescence recognition property for metal ions. Acta Polymerica Sinica, 2024, 55(10), 1335-1345 DOI： 10.11777/j.issn1000-3304.2024.24055.

摘要

以微晶纤维素为基质，通过6-位保护法和氨基甲酸酯化反应，合成了一种6-位具有大体积咔唑侧基的区域选择性取代纤维素类衍生物，即纤维素-[2

3-(3

5-二甲基)-6-(4-(4-(3-(9-乙基-9H-咔唑-3)脲基)苄基))

]

苯基氨基甲酸酯(Cel-1). 由核磁共振氢谱和元素分析结果表明所合成衍生物的结构规整，取代基本完全. 基于12种金属离子对Cel-1的荧光识别性能进行了详细评价. 结果表明，大体积纤维素衍生物Cel-1可在DMSO/H

O体系中对Fe

和Cu

实现高灵敏度和高选择性的双模式检测，同时对其他10种金属离子均有极好的抗干扰能力. 其中，在荧光模式和紫外可见光模式下，Cel-1对Fe

和Cu

的检测限均低于美国国家环境保护局(EPA)所规定的2种离子在饮用水中可接受的最高浓度. 证明所合成的大体积纤维素类衍生物具有对Fe

和Cu

的高效特异性荧光识别性能，可作为化学传感器用于这2种金属离子的快速识别与检测. 此外，基于Cel-1制备的荧光墨水在自然光下不显示，但在紫外光下则可观察到明亮的蓝色荧光，显示了其在防伪领域的应用潜能.

Abstract

A regioselectively substituted cellulose derivative with bulky pendants at the 6-position

that is the cellulose-‍[2

‍3-‍(3

‍5-dimethyl)-6-(4-‍(4-‍(3-‍(9-ethyl-9H-carbazole-3)ureido)benzyl))

]

phenylcarbamate (Cel-1)

was successfully synthesized using cellulose as substrate by 6-position-protection method and carbamoylation. The

H-NMR spectrum and elemental analysis data indicated that the cellulose derivative was structurally regular with almost complete substitution as expected. The fluorescent recognition property of Cel-1 was then evaluated in detail based on twelve metal ions. The results indicated that the bulky cellulose derivative (Cel-1) could realize excellent dual-mode recognition to both Fe

and Cu

with high sensitivity and high selectivity in the DMSO/H

O system

together with high anti-counterfeiting ability to the other ten metal ions tested in the study. Especially

the limits of detection of Cel-1 for Fe

and Cu

in both fluorescence and UV

-visible modes were lower than the maximum acceptable concentrations of the two ions in drinking water as defined by the United States Environmental Protection Agency (EPA). It demonstrated that the obtained bulky cellulose derivative possessed high-efficient and specific fluorescent recognition ability for Fe

and Cu

which could be used as chemosensors for the rapid recognition and detection of the two metal ions. In addition

the fluorescent ink prepared based on Cel-1 could not be observed under natural light

whereas emitted bright blue fluorescence under ultraviolet light

suggesting its potential in the anti-counterfeiting related field.

关键词

荧光传感大体积侧基纤维素类衍生物金属离子识别双模式检测

Keywords

Fluorescent sensingBulky pendantsCellulose derivativesMetal ion recognitionDual mode detection

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