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Issue 11, 2016
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Fluorinated antimony(v) derivatives: strong Lewis acidic properties and application to the complexation of formaldehyde in aqueous solutions

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Abstract

As part of our ongoing studies of water tolerant Lewis acids, we have synthesized and investigated the properties of Sb(C6F5)3(O2C6Cl4), a fluorinated stiborane whose Lewis acidity approaches that of B(C6F5)3. While chloroform solutions of this Lewis acid can be kept open to air or exposed to water for extended periods of time, this new Lewis acid reacts with PtBu3 and paraformaldehyde to form the corresponding formaldehyde adduct tBu3P–CH2–O–Sb(C6F5)3(O2C6Cl4). To test if this reactivity can also be observed with systems that combine the phosphine and the stiborane within the same molecule, we have also prepared o-C6H4(PPh2)(SbAr2(O2C6Cl4)) (Ar = Ph, C6F5). These yellow compounds, which possess an intramolecular P→Sb interaction, are remarkably inert to water but do, nonetheless, react with and accomodate formaldehyde into the P/Sb pocket. In the case of the fluorinated derivative o-C6H4(PPh2)(Sb(C6F5)2(O2C6Cl4)), formaldehyde complexation, which occurs in water/dichloromethane biphasic mixtures, is accompanied by a colourimetric turn-off response thus highlighting the potential that this chemistry holds in the domain of molecular sensing.

Graphical abstract: Fluorinated antimony(v) derivatives: strong Lewis acidic properties and application to the complexation of formaldehyde in aqueous solutions

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Publication details

The article was received on 09 Jun 2016, accepted on 09 Jul 2016 and first published on 11 Jul 2016


Article type: Edge Article
DOI: 10.1039/C6SC02558G
Chem. Sci., 2016,7, 6768-6778
  • Open access: Creative Commons BY license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    Fluorinated antimony(V) derivatives: strong Lewis acidic properties and application to the complexation of formaldehyde in aqueous solutions

    D. Tofan and F. P. Gabbaï, Chem. Sci., 2016, 7, 6768
    DOI: 10.1039/C6SC02558G

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