Rapid synthesis of a BODIPY derivative serving as a highly selective and sensitive fluorescence chemosensor for Hg2+ ion detection

We synthesized 2-amino-1,3-propanediol-modified boron dipyrromethene (BODIPY) in a rapid two-step synthesis, with a total reaction time of 6 hours. The resulting fluorophore's emission was significantly quenched by polar solvents but increased fourfold upon the addition of Hg2+ ions. Notably, t...

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Bibliographic Details
Published in:New journal of chemistry 2024-10, Vol.48 (39), p.17064-17070
Main Authors: Shun-Qiang Xu, Ting-Yu, Yang, Po-Tan, Huang, Chi-Heng, Yang, Khantamat, Orawan, Leong-Perng Chan, Chien-Hung, Li
Format: Article
Language:English
Subjects:
Binding
Calcium ions
Chemical sensors
Chemical synthesis
Chemoreceptors
Cobalt
Emission
Ethylenediaminetetraacetic acids
Fluorescence
Infrared spectroscopy
Mercury (metal)
NMR
Nuclear magnetic resonance
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Summary:We synthesized 2-amino-1,3-propanediol-modified boron dipyrromethene (BODIPY) in a rapid two-step synthesis, with a total reaction time of 6 hours. The resulting fluorophore's emission was significantly quenched by polar solvents but increased fourfold upon the addition of Hg2+ ions. Notably, this BODIPY fluorophore exhibited high selectivity toward Hg2+ ions over various other metal ions (Li+, Na+, K+, Ca2+ Co2+, Cu2+, Ni2+, Pb2+, Zn2+, Mn3+, Ag+, and Fe3+), with a binding constant of 7.36 × 104 M−1. The binding mechanism was investigated using proton nuclear magnetic resonance (1H NMR) and infrared (IR) spectroscopy and revealed that 2-amino-1,3-propanediol moieties chelated the Hg2+ ions. These chelated Hg2+ ions could be displaced by hexadentate EDTA molecules. Furthermore, treating BODIPY with an acid restored fluorescence emission, while a base diminished it, and this process was reversible. This rapidly synthesized BODIPY fluorophore holds great potential for Hg2+ ion detection.
ISSN:1144-0546
1369-9261
DOI:10.1039/d3nj03275b