Axially chiral 1,4-dihydropyridine derivatives: aggregation-induced emission in exciplexes and application as viscosity probes |
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Authors: | Zeren Yang Yanmin Huo Yanke Liu Guifen Du Wenhao Zhang Lijie Zhou Lihui Zhan Xuerui Ren Wenzeng Duan Shuwen Gong |
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Affiliation: | Institute of Functional Organic Molecules and Materials, School of Chemistry and Chemical Engineering, Liaocheng University, No. 1 Hunan Road, Liaocheng 252000 People''s Republic of China, |
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Abstract: | By combining the fluorophores of axially chiral 1,1′-binaphthol (BINOL) and 1,4-dihydropyridine derivatives, axially chiral 1,4-dihydropyridine derivatives ((R)-/(S)-2) with aggregation-induced emission (AIE) in exciplexes were designed and synthesized. (R)-/(S)-2 emitted low fluorescence in THF solutions of their locally excited states; however, they emitted red-shifted fluorescence in the aggregate state upon exciplex formation. Moreover, (R)-/(S)-2 showed linear and multi-exponential relationships between their local excited and exciplex fluorescence intensities and the viscosity of the medium, which allowed us to determine the viscosities of different mixed solvents. In addition, as an axially chiral viscosity probe, (R)-/(S)-2 show excellent CD signals and have potential applications in the fields of chiral recognition and fluorescence imaging, which will broaden the new family of AIE fluorophores. To the best of our knowledge, there are few reports of axially chiral intramolecular exciplex-mediated AIE molecules.Axially chiral 1,4-dihydropyridine derivatives ((R)-/(S)-2) with aggregation-induced emission (AIE) in exciplex were designed and synthesized. They have excellent CD signals and can determine the different viscosity in mixed solvents. |
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