有机化学 ›› 2022, Vol. 42 ›› Issue (11): 3757-3765.DOI: 10.6023/cjoc202204026 上一篇    下一篇

所属专题: 有机氟化学虚拟合辑

研究论文

一种基于氟硼二吡咯(BODIPY)衍生物的高选择性“Off-On”型Cu2+比色-荧光探针

赵小龙a,*(), 李宇晴a, 郭亮武a, 冉启元a, 吴会慧a, 张祯a, 苏瀛鹏a, 周鹏鑫a, 燕娜b   

  1. a西北师范大学化学化工学院 教育部生态环境相关高分子重点实验室 兰州 730070
  • 收稿日期:2022-04-11 修回日期:2022-07-06 发布日期:2022-07-20
  • 通讯作者: 赵小龙
  • 基金资助:
    甘肃省高等学校产业支撑计划(2021CYZC-17); 甘肃省自然科学基金(21JR1RA227); 国家自然科学基金(21462039)

A Highly Selective and High-Contrast Colorimetric “Off-On” Chemosensor for Cu2+ Based on Boron-Dipyrromethene (BODIPY) Derivatives

Xiaolong Zhaoa(), Yuqing Lia, Liangwu Guoa, Qiyuan Rana, Huihui Wua, Zhen Zhanga, Yingpeng Sua, Pengxin Zhoua, Na Yanb   

  1. aKey Laboratory of Eco-Environment-Related Polymer Materials, Ministry of Education, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070
    b兰州大学药学院 兰州 730000
  • Received:2022-04-11 Revised:2022-07-06 Published:2022-07-20
  • Contact: Xiaolong Zhao
  • Supported by:
    Gansu Provincial Industrial Support Program for Colleges(2021CYZC-17); Natural Science Foundation of Gansu Province(21JR1RA227); National Natural Science Foundation of China(21462039)

开发了一种水溶性良好的荧光增强型氟硼二吡咯(BODIPY)探针BDP-2Z. 在较宽的pH范围(pH=3.0~12.0)内探针对Cu2+表现出低检测限、快速响应、高灵敏度和选择性等优势. Cu2+引起的颜色和荧光对比非常显著, 能实现 Cu2+的可视化检测. 通过柱层析法分离得到识别过程的水解产物, 并利用紫外和荧光光谱、质谱分析证实了识别机制. 此外, 在真实水样中的快速裸眼识别扩展了其在环境检测方面的应用.

关键词: 水溶性, 可视化, BODIPY衍生物, 荧光增强

Based on the platform of boron-dipyrromethene (BODIPY) derivatives, a fluorescence turn-on probe BDP-2Z was rationally designed and synthesized with good water-solubility. With high sensitivity and selectivity for Cu2+ over other competitive ions, the reaction-based probe showed low detection limit and fast response in a wide pH range (pH=3.0~12.0). The contrast of color and fluorescence caused by Cu2+ was remarkable so much so that it was easily to distinguish Cu2+ from other ions with naked-eye detection. Along with adding of Cu2+, a blue shift of maximum absorption was observed from 548 nm to 496 nm, the corresponding solution color changed obviously from purple to light orange, and the fluorescence is enhanced by nearly 5-fold. Furthermore, the recognition mechanism was confirmed by UV-Vis, fluorescence spectra, and mass spectral analysis. The identified product of recognition process was even obtained by original silica gel column chromatography separation method. Also, the rapidly naked-eye application in real water samples provides an alternative to extension environmental detection.

Key words: water-soluble, naked-eye, BODIPY derivatives, fluorescence turn-on