Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 1, Pages 195-201Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201302638
Keywords
aggregation-induced emission; nitrophenols; explosives; fluorescent probes; sensors; Schiff-base macrocycles
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Funding
- National Natural Science Foundation of China [21072067]
- Analytical and Testing Centre at Huazhong University of Science and Technology
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A tetraphenylethylene (TPE) Schiff-base macrocycle showing an aggregation-induced emission (AIE) effect has been synthesized, which could aggregate into nanospheres and emit yellow fluorescence in aqueous media. By virtue of its AIE effect, the macrocycle showed a sensitive and selective response to 2,4,6-trinitrophenol (TNP) and 2,4-dinitrophenol (DNP) among a number of nitroaromatic compounds, which could be used to detect TNP and DNP at nanomolar levels. Moreover, it exhibited a superamplified quenching effect with DNP but not with TNP, providing a possible means of discriminating these two compounds. In comparison with open-chain TPE Schiff-bases, the cavity of the macrocycle is essential for the selectivity for DNP over TNP. In addition, quantitative analyses of both DNP and TNP in real water samples and qualitative detection of these two analytes in the solid state by the macrocycle have been tested. The reliability of the quantitative analysis has been confirmed by HPLC. Our findings demonstrate that the TPE Schiff-base macrocycle has great potential as an excellent sensor for DNP and TNP.
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