Aggregation induced emission enhancement behavior of conformationally rigid pyreneamide-based probe for ultra-trace detection of picric acid (PA)
- Authors
- Kumar, Ashwani; Chae, Pil Seok
- Issue Date
- Sep-2018
- Publisher
- Elsevier BV
- Keywords
- AIEE; Pyreneamide; Excimer emission; PA; Vapor sensing
- Citation
- Dyes and Pigments, v.156, pp.307 - 317
- Indexed
- SCIE
SCOPUS
- Journal Title
- Dyes and Pigments
- Volume
- 156
- Start Page
- 307
- End Page
- 317
- URI
- https://scholarworks.bwise.kr/erica/handle/2021.sw.erica/5648
- DOI
- 10.1016/j.dyepig.2018.04.014
- ISSN
- 0143-7208
- Abstract
- In this study, we designed and prepared pyrene-based dipodal probes with a range of molecular flexibility for picric acid (PA) detection. These probes commonly contain a central rigid core, but probe 1 contains relatively short linkers/spacers compared to probes 2 and 3. The dipodal probes produced dominant pyrene excimer fluorescence in an aqueous solution, and aggregation-induced emission enhancement (AIEE) was observed. The fluorescence emission of probe I was significantly quenched only by the presence of PA, while probes 2 and 3 were responsive to 4-nitrophenol or 2,4-dinitrophenol as well as PA. Of the three dipodal probes, the highest binding strength was observed for probe 1 with PA, which gave an association constant of K-alpha = 3.96 x 10(7) M-1.H-1 NMR measurements and DFT calculations indicate that, upon addition of PA, these dipodal probes formed individual probe-PA complexes via pi-pi interactions between the pyrene ring and PA in an aqueous solution. This complex formation enabled energy transfer from electron-rich pyrene to electron-poor PA upon excitation, leading to fluorescence quenching. Probe 1 provided ultra-trace detection of PA in water, with observed and calculated limit of detections (LOD) of 1 nM and 0.13 pM, respectively, one of the lowest values reported. Effective fluorescence quenching was also obtained using probe 1-coated filter paper or TLC plate with PA solution/vapor, suggesting the significant potential of this sensing system in real-time applications. These studies were supported by FE-SEM, TEM, and UV-visible, fluorescence, NMR and DFT calculations.
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