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Characterization of the Aggregation-Induced Enhanced Emission of N,N′-bis(4-methoxysalicylide)benzene-1,4-diamine

Journal of Fluorescence volume 25, pages 1183–1189 (2015)Cite this article

Abstract

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.

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Acknowledgments

We are grateful for the financial support from the Natural Science Foundation of China (No. 21165006), the Fund of the International cooperation projects of Guizhou Province (No. 20137002) and “Chun-Hui” Fund of Chinese Ministry of Education (No. Z2011033, Z2012053). The EPSRC is thanked for financial support (Overseas Travel award to CR).

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Authors and Affiliations

  1. Key Laboratory of Macrocycle and Supramolecular Chemistry of Guizhou Province, Guiyang, 550025, China

    Fuyong Wu, Guangjun Xu, Xi Zeng & Lan Mu

  2. Department of Chemistry, University of Hull, Hull, HU6 7RX, UK

    Carl Redshaw

  3. CSIRO Manufacturing Flagship, PO Box 218, Lindfield, NSW, 2070, Australia

    Gang Wei

Authors
  1. Fuyong Wu
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  2. Guangjun Xu
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  3. Xi Zeng
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  4. Lan Mu
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  5. Carl Redshaw
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  6. Gang Wei
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Correspondence to Lan Mu or Gang Wei.

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Wu, F., Xu, G., Zeng, X. et al. Characterization of the Aggregation-Induced Enhanced Emission of N,N′-bis(4-methoxysalicylide)benzene-1,4-diamine. J Fluoresc 25, 1183–1189 (2015). https://doi.org/10.1007/s10895-015-1605-2

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  • DOI: https://doi.org/10.1007/s10895-015-1605-2

Keywords

  • Salicylaldehyde derivative
  • Aggregation-induced emission enhancement
  • Fluorescence probe
  • Volatile organic solvent