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

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
• 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
• 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
• Contract Date: Nov 24, 2015