1. Dual-state emissive imidazo[1,2-α]pyridines with full color emission, acidochromism, viscosity-dependent fluorescence, and bioimaging applications.
- Author
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Zhu, Yujie, Liao, Kaihao, Li, Yigao, Zhang, Wenjing, Song, Bing, Hao, Xin-Qi, and Zhu, Xinju
- Subjects
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FLUORESCENCE , *IMIDAZOPYRIDINES , *CYTOCOMPATIBILITY , *MOLECULAR conformation , *CELL permeability , *FLUOROPHORES , *VISCOSITY , *DELAYED fluorescence - Abstract
Five novel dual-state emissive imidazo[1,2- α ]pyridine-based luminogens IP1-5 were rationally designed and prepared by varying the conjugation length and the nature of donor-acceptor (D-A) units. These D-A chromophores displayed cyan, green, yellow, and red fluorescence in the solid state, with full-color emission achieved for the first time through modification of imidazo[1,2- α ]pyridine core. Interestingly, IP1 and IP5 in the solid state exhibited an abnormal remarkable blue-shift emission compared with those in THF, probably due to the highly twisted molecular conformations and solvent effect by theoretical calculations as well as crystal structure analyses. Importantly, IP1-5 revealed remarkable reversible acid-induced acidichromism, accompanied with dual change of colorimetric and fluorometric determination. Viscosity-dependent fluorescence was next conducted, indicting IP1-3 can be utilized for local viscosity detection. Moreover, IP1-5 served as promising candidates for multicolor bioimaging with low cell toxicity and good biocompatibility. Five asymmetric donor-acceptor dual-state emissive imidazo[1,2- ɑ ]pyridines have been synthesized with full color emission acidichromism, viscosity-dependent fluorescence, and biological imaging. [Display omitted] • Five DSE fluorophores IP1-5 based on carbonyl-substituted imidazo[1,2- α ]pyridine have been synthesized and characterized. • IP1-5 exhibited full color solid emission through manipulation of D-A electronic structures and conjugation length. • IP1-5 displayed reversible acidochromism and bioimaging applications with excellent biocompatibility and cell permeability. • IP1-3 showed viscosity-dependent fluorescence with application as potential viscosity sensors. [ABSTRACT FROM AUTHOR]
- Published
- 2024
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