Enhancing water sensing via aggregation-induced emission (AIE) and solvatofluorochromic studies using two new dansyl derivatives containing a disulfide bound: Pollutant metal ions detection and preparation of water-soluble fluorescent polymeric particles

17 April 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Polarity-sensitive dansyl derivatives L1 and L2 were synthesized, and their ability to sense pollutant metal ions was investigated. All compounds were highly sensitive towards Cu2+ and Hg2+ metal ions, while L2 could detect and quantify Hg2+ concentrations as low as 2.5 µM. Both L1 and L2 exhibit positive solvatofluorochromic behaviour, modulated in the presence of water, which in turn results in fluorescence enhancement via aggregation-induced emission (AIE). Seeking stability and water solubility, luminescent L1-based polystyrene-block-polybutadiene-block-polystyrene (SBS) microparticles (size: 520 ± 76 nm) were successfully prepared while maintaining the fluorescence emission of fluorophore L1 (22%). This work shows the dansyl-derivative's multiple properties and promising applications in biomedicine and environmental fields.

Keywords

Microparticles
dansyl derivatives
metal ions
AIE effect
Solvatochromism
polystyrene-block-polybutadiene-block-polystyrene (SBS)

Supplementary materials

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Title
Enhancing water sensing via aggregation-induced emission (AIE) and solvatofluorochromic studies using two new dansyl derivatives containing a disulfide bound: Pollutant metal ions detection and preparation of water-soluble fluorescent polymeric particles
Description
Figure S1. 1H-NMR spectrum of compound 3. Figure S2. 13C-NMR spectrum of compound 3. Figure S3. 1H-NMR spectrum of compound L1. Figure S4. 13C-NMR spectrum of compound L1. Figure S5. 1H-NMR spectrum of compound L2. Figure S6. 13C-NMR spectrum of compound L2. Figure S7. ESI-HRMS spectrum of compound L1. Figure S8. ESI-HRMS spectrum of compound L2. Figure S9. Emission, excitation and solid-state emission spectra of compound L1 in 1) acetonitrile, 2) ethanol and 3) DMSO ([L1] = 6 μM). Figure S10. Emission, excitation, and solid-state emission spectra of compound L1 in 4) chloroform, 5) toluene and 6) THF ([L1] = 6 μM). Figure S11. Emission, excitation and solid-state emission spectra of compound L2 in 1) acetonitrile, 2) ethanol and 3) DMSO ([L2] = 6 μM). Figure S12. Emission, excitation, and solid-state emission of compound L2 in 4) chloroform, 5) toluene and 6) THF ([L2] = 6 μM).
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