Exploring Fluorous Affinity by Liquid Chromatography

Martina Catani, Roberta Guzzinati, Nicola Marchetti, Luisa Pasti, Alberto Cavazzini

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13 Citations (Scopus)

Abstract

Terms such as "fluorous affinity" and "fluorophilicity" have been used to describe the unique partition and sorption properties often exhibited by highly fluorinated organic compounds, that is molecules rich in sp3 carbon-fluorine bonds. In this work, we made use of a highly fluorinated stationary phase and a series of benzene derivatives to study the effect of one single perfluorinated carbon on the chromatographic behavior and adsorption properties of molecules. For this purpose, the adsorption equilibria of α,α,α-trifluorotoluene, toluene, and other alkylbenzenes have been studied by means of nonlinear chromatography in a variety of acetonitrile/water eluents. Our results reveal that one single perfluorinated carbon is already enough to induce a drastic change in the adsorption properties of molecules on the perfluorinated stationary phase. In particular, it has been found that adsorption is monolayer if the perfluoroalkyl carbon is present but that, when this unit is missing, molecules arrange as multilayer stack structures. These findings can contribute to the understanding of molecular mechanisms of fluorous affinity. (Figure Presented).
Original languageEnglish
Pages (from-to)6854 - 6860
Number of pages7
JournalAnalytical Chemistry
Volume87
Issue number13
DOIs
Publication statusPublished - 7 Jul 2015
Externally publishedYes

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All Science Journal Classification (ASJC) codes

  • Analytical Chemistry

Cite this

Catani, M., Guzzinati, R., Marchetti, N., Pasti, L., & Cavazzini, A. (2015). Exploring Fluorous Affinity by Liquid Chromatography. Analytical Chemistry, 87(13), 6854 - 6860. https://doi.org/10.1021/acs.analchem.5b01212