High dual-state blue emission of a functionalized pyrazoline derivative for picric acid detection

Developing dual-state fluorescence materials with high emission efficiency both in solution and solid states is still a challenge. Herein, a functionalized pyrazoline derivative ( NF ) was designed and synthesized. NF exhibited high blue emission efficiency in both THF solution and solid states with...

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Bibliographic Details
Published in:CrystEngComm 2021-01, Vol.23 (1), p.221-226
Main Authors: Guo, Shengmei, Zhang, Yuyang, Huang, Jianyan, Kong, Lin, Yang, Jiaxiang
Format: Article
Language:English
Subjects:
Crystal structure
Crystallography
Electron transfer
Emission spectra
Energy transfer
Fluorescence
Molecular structure
NMR
Nuclear magnetic resonance
Single crystals
Steric hindrance
Structural analysis
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Summary:Developing dual-state fluorescence materials with high emission efficiency both in solution and solid states is still a challenge. Herein, a functionalized pyrazoline derivative ( NF ) was designed and synthesized. NF exhibited high blue emission efficiency in both THF solution and solid states with the absolute fluorescence quantum yields of 58% and 43%, respectively. The mechanism of this unique fluorescence behavior was systematically studied with the help of single-crystal structure analysis. The results showed that a close-knit molecular structure existed due to intramolecular C-H π interactions, which can impair the intramolecular rotation to accelerate the radiative transition in the mono-molecule state (in dilute solution). Moreover, the steric hindrance and intermolecular hydrogen-bond interactions of the substituent groups can restrict the close packing and prompt the formation of J-aggregates in the aggregation state, which resulted in high emission performance in the solid state. Meanwhile, the dual-state blue emission property of NF was utilized for the picric acid (PA) detection in the solution state and on a test paper by the synergistic effects of photo-induced electron transfer (PET) and Förster resonance energy transfer (FRET) processes. The limit of detection as low as 6.80 × 10 −7 M achieved in the THF-H 2 O mixture. This work provided a new scope for the design of high dual-state blue emission materials. High dual-state blue emission of a functionalized pyrazoline derivative for picric acid detection.
ISSN:1466-8033
1466-8033
DOI:10.1039/d0ce01195a