title: Exploring Fluorous Affinity by Liquid Chromatography.
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 sp(3) 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.
authors.affiliation: †University of Ferrara, Department of Chemistry and Pharmaceutical Sciences, Via L. Borsari, 46, 44121 Ferrara, Italy.
authors.forename: Martina
authors.initials: M
authors.lastname: Catani
authors.affiliation: †University of Ferrara, Department of Chemistry and Pharmaceutical Sciences, Via L. Borsari, 46, 44121 Ferrara, Italy.|‡Italian National Agency for New Technologies, Energy and Sustainable Economic Development (ENEA), R. C. Casaccia, Via Anguillarese, 301, S. Maria di Galeria, 00123, Roma, Italy.
authors.forename: Roberta
authors.initials: R
authors.lastname: Guzzinati
authors.affiliation: †University of Ferrara, Department of Chemistry and Pharmaceutical Sciences, Via L. Borsari, 46, 44121 Ferrara, Italy.
authors.forename: Nicola
authors.initials: N
authors.lastname: Marchetti
authors.affiliation: †University of Ferrara, Department of Chemistry and Pharmaceutical Sciences, Via L. Borsari, 46, 44121 Ferrara, Italy.
authors.forename: Luisa
authors.initials: L
authors.lastname: Pasti
authors.affiliation: †University of Ferrara, Department of Chemistry and Pharmaceutical Sciences, Via L. Borsari, 46, 44121 Ferrara, Italy.
authors.forename: Alberto
authors.initials: A
authors.lastname: Cavazzini
mesh_terms: D000327:Adsorption; D002846:Chromatography, Affinity / Q000379:methods*; D005461:Fluorine / Q000737:chemistry*
chemical_list: D005461:Fluorine