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Characterization of the aggregation-induced enhanced emission of N,N'-bis(4-methoxysalicylide)benzene-1,4-diamine

Wu, Fuyong; Xu, Guangjun; Zeng, Xi; Mu, Lan; Redshaw, Carl; Wei, Gang

Authors

Fuyong Wu

Guangjun Xu

Xi Zeng

Lan Mu

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Professor Carl Redshaw C.Redshaw@hull.ac.uk
Professor of Inorganic Materials Chemistry and REF Lead for Chemistry

Gang Wei



Abstract

© 2015 Springer Science+Business Media New York. N,N′-bis(4-methoxysalicylide)benzene-1,4-diamine (S1) was synthesized from 4-methoxysalicylaldehyde and p-phenylenediamine and it was found to exhibit interesting aggregation-induced emission enhancement (AIEE) characteristics. In aprotic solvent, S1 displayed very weak fluorescence, whilst strong emission was observed when in protic solvent. The morphology characteristics and luminescent properties of S1 were determined from the fluorescence and UV absorption spectra, SEM, fluorescence microscope and grading analysis. Analysis of the single crystal diffraction data infers that the intramolecular hydrogen bonding constitutes to a coplanar structure and orderly packing in aggregated state, which in turn hinders intramolecular C-N single bond rotation. Given that the three benzene rings formed a large plane conjugated structure, the fluorescence emission was significantly enhanced. The absolute fluorescence quantum yield and fluorescence lifetime also showed that radiation transition was effectively enhanced in the aggregated state. Moreover, the AIEE behavior of S1 suggests there is a potential application in the fluorescence sensing of some volatile organic solvents.

Citation

Wu, F., Xu, G., Zeng, X., Mu, L., Redshaw, C., & Wei, G. (2015). Characterization of the aggregation-induced enhanced emission of N,N'-bis(4-methoxysalicylide)benzene-1,4-diamine. Journal of fluorescence, 25(5), 1183-1189. https://doi.org/10.1007/s10895-015-1605-2

Journal Article Type Article
Acceptance Date Jun 30, 2015
Online Publication Date Jul 14, 2015
Publication Date Sep 1, 2015
Deposit Date Nov 24, 2015
Publicly Available Date Nov 24, 2015
Journal Journal of fluorescence
Print ISSN 1053-0509
Electronic ISSN 1573-4994
Publisher Springer Verlag
Peer Reviewed Peer Reviewed
Volume 25
Issue 5
Pages 1183-1189
DOI https://doi.org/10.1007/s10895-015-1605-2
Keywords Salicylaldehyde derivative, Aggregation-induced emission enhancement, Fluorescence probe, Volatile organic solvent
Public URL https://hull-repository.worktribe.com/output/381749
Publisher URL http://link.springer.com/article/10.1007%2Fs10895-015-1605-2
Copyright Statement ©2016 University of Hull
Additional Information Authors' accepted manuscript of article published in: Journal of fluorescence, 2015, v.25, issue 5. The final publication is available at Springer via http://dx.doi.org/10.1007/s10895-015-1605-2

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