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Updated: Jun 15, 2025

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Highly Reversible "On-Off-On" Fluorescence Switch Governed by pH, Utilizing Bis(Benzimidazole) Derivatives with
Weijian Xue1, Xiangyu Ling2, Huiqian Li2
1Heilongjiang Provincial Key Laboratory of Surface Active Agent and Auxiliary, Technology Innovation Center of Industrial Hemp for State Market Regulation, Institute of Chemistry and Chemical Engineering, Qiqihar University, Qiqihar, 161006, PR China. hehexueweijian@163.com.
Abstract:
In this work, a series of dibenzimidazole derivatives 1-4, act as highly reversible colorimetric and fluorescent pH chemosensor, were designed and synthesized. Excellent reversible pH response of these sensors could be found by a specific pH change through obvious fluorescent color changes. The response is not affected by common cations (including Al3+, Cu2+, Ca2+, Cd2+, Co2+, Cr3+, Mg2+, Na+, K+, Ni2+, Pb2+ and Zn2+) and anions (including F-, Cl-, Br-, I-, ClO4-, H2PO4-, HSO4-, HCO3- and CH3COO-). Notably, these sensors can be reused more than 10 times without losing functionality. Unlike previous reports, the distinct properties of 1-4 are attributed to the varied link groups. Based on comprehensive experimental data and mechanistic analyses, it is concluded that sensors 1-4 are promising candidates for use as highly reversible "on-off-on" fluorescence switches under precise pH control.
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