Journal
SUPRAMOLECULAR CHEMISTRY
Volume 32, Issue 9, Pages 508-517Publisher
TAYLOR & FRANCIS LTD
DOI: 10.1080/10610278.2020.1825715
Keywords
Organic polymers; Troger's base; 1; 8-naphthalimide; fluorescence; chemosensing; nitroaromatics
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Funding
- H2020 European Research Council [CoG SUPRAMOL 2014-647719]
- Science and Engineering Research Board [EMEQ Award] [EEQ/2018/000799]
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A new hyper-crosslinked 4-amino-1,8-naphthalimide Troger's base containing pyridinium covalent organic polymer,TBNap-COP, was synthesised and employed as a 'turn-off' fluorescent chemosensor for nitroaromatic explosives.TBNap-COPwas synthesised in quantitative yield using a one-step nucleophilic substitution reaction between a dipyridyl scaffold (TBNap, bis-[N-(2-(pyridine-4-yl)ethyl)]-9,18-methano-1,8-naphthalimide-[b,f][1,5]diazocine) and 1,3,5-tris(bromomethyl)benzene by heating in DMF for 3 days. The formation and phase-purity ofTBNap-COPwere fully characterised by using various spectroscopic and microscopy analyses. The suspension ofTBNap-COPin water showed strong fluorescence emission characteristics owing to the 'push-pull' based ICT transition and it was used as a fluorescent sensor for discriminative detection of nitroaromatic explosives.TBNap-COPdisplayed selective fluorescence quenching responses for phenolic-nitroaromatics, with particularly high sensitivity for picric acid which is a powerful secondary chemical explosive and a harmful environmental pollutant widely used in the dye industries.
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