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Issue 42, 2009
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Colorimetric turn-on sensing of fluoride ions in H2O/CHCl3 mixtures by pyridinium boranes

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Abstract

As part of our interest in chemistry of cationic boron compounds as anion receptors, we have synthesized 2-(4′-dimestylborylphenyl)-N-methyl-pyridinium triflate ([3]OTf) and 2-(5′-dimesitylborylthiophen-2′-yl)-N-methyl-pyridinium triflate ([4]OTf) by reaction of the corresponding pyridyl derivatives with MeOTf. Both [3]OTf and [4]OTf extract fluoride ions biphasically (H2O/CHCl3) to form the zwitterionic fluoroborates 3-F and 4-F, which have been structurally characterized. Remarkably, fluoride binding induces a red-shift of the low energy absorption band of these boranes (from 319 nm to 368 nm for 3/3-F and from 355 nm to 430 nm for 4/4-F) leading to the appearance of a yellow color. The origin of this turn-on colorimetric response is attributed to an intramolecular charge transfer process involving the triorganofluoroborate moiety as the donor and the pyridinium moiety as the acceptor.

Graphical abstract: Colorimetric turn-on sensing of fluoride ions in H2O/CHCl3 mixtures by pyridinium boranes

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Publication details

The article was received on 01 Jul 2009, accepted on 29 Jul 2009 and first published on 03 Sep 2009


Article type: Paper
DOI: 10.1039/B913030F
Dalton Trans., 2009, 9169-9175

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    Colorimetric turn-on sensing of fluoride ions in H2O/CHCl3 mixtures by pyridinium boranes

    C. R. Wade and F. P. Gabbaï, Dalton Trans., 2009, 9169
    DOI: 10.1039/B913030F

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