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Science China Chemistry

Science China Chemistry

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Multistimuli-responsive dual-state emissive imidazo[1,2-α]pyridine as imaging probe for lipid droplets

Published:2 September 2025 DOI: 10.1007/s11426-025-2835-x
Yu Yuan, Xinran Zhao, Yueli Zhao, Wenjing Zhang, Shuai Lu, Bing Song, Xinju Zhu, Xin-Qi Hao, Shuang-Quan Zang

Abstract

Organic fluorescent materials with multistimuli-responsive behaviors have attracted much attention because of their promising applications in diverse fields. Most chromophores exhibit bright emission in either dilute solutions or aggregation states, which inevitably suffer from the aggregation-caused quenching (ACQ) problem or encounter serious energy loss at low concentration. To overcome these limitations, dual-state emissive (DSE) materials with bright emission in both solution and solid states have been developed. However, most DSE materials only involve one or two stimulus-responsive behaviors. Herein, through combining characteristics of imidazopyridine N1 as well as manipulation of electronic structure and intermolecular interaction, DSE molecule TPA-IPBA with four multistimuli-responsive behaviors has been rationally and accurately prepared, which could be easily converted to ACQ (TPA-IPB) and AIE (aggregation-induced emission) (TPA-IPBCN) molecules. Under external stimuli, four types of multistimuli-responsive behaviors have been successfully achieved, including solvatochromism (redshift of 124 nm), mechanofluorochromism (redshift of 6 or 30 nm), reversible tricolor acidichromism (redshift of 148 nm) and solid-phase polymorphism with solvent-dependent solid emission (from B-state to G-state, redshift of 52 nm). We explained four types of multistimuli-responsive behaviors in detail through nuclear magnetic resonance spectroscopies, theoretical calculations, single crystal analysis, and PXRD characterization. In addition, on the basis of our biological research on imidazo[1,2-α]-pyridines, we found that TPA-IPBA serves as a fluorescent probe to dynamically detect biological lipid droplets with high co-localization ability (PC = 0.95). These results provide new insight into developing DSE materials via a delicate manipulation of molecular structure with acceptor-dependent tunable multistimuli-responsive properties and bioimaging applications.

Substances (4)

Materials
Procduct Name CAS Molecular Formula Supplier Price
Nile Red 7385-67-3 C20H18N2O2 365 suppliers $5.00-$1873.00
Nile Red 7385-67-3 C20H18N2O2 365 suppliers $5.00-$1873.00
Nile Red 7385-67-3 C20H18N2O2 365 suppliers $5.00-$1873.00
Nile Red 7385-67-3 C20H18N2O2 365 suppliers $5.00-$1873.00

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