A convenient access toward novel fluoroionophores based on 1-(2-pyridyl)-4-styrylpyrazoles (PSPs) substituted at position 3 with donor or acceptor aryl groups is reported. The synthesis proceeds in two steps: the first one via Wittig olefination of the appropriate 4-formylpyrazole and then Mizoroki-Heck coupling to yield the desired products in an overall yield of up to 69%. Photophysical properties of products (4-styryl) and their intermediates (4-vinyl) were explored, finding that they have strong blue-light emission with high quantum yields (up to 66%) due to ICT phenomena. The 3-phenyl PSP was studied as a turn-off fluorescent probe in metal ion sensing, finding a high selectivity to Hg (LOD = 3.1 × 10 M) in a process that could be reversed with ethylenediamine. The sensing mechanism and binding mode of the ligand to Hg were established by HRMS analysis and H NMR titration tests.
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| http://dx.doi.org/10.1021/acsomega.9b02796 | DOI Listing |
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