Fluorophobic effect promotes partitioning of organics into macroporous organic polymers: a method for achieving high local concentrations

Journal of the American Chemical Society
Shannon M Leeder, M R Gagne

Abstract

The efficiency for partitioning small organic compounds from fluorinated solvents of varying quality into highly cross-linked, macroporous, and insoluble organic polymers is described. The solvating qualities of the poly(acrylates) together with the solvating quality of the solvent are key to describing the partitioning thermodynamics. Partitioning measurements for 9-anthracene methanol 1 are reported as a function of fluorous content in perfluoromethylcyclohexane (PFMC):hexanes mixtures, comonomer structure and loading, and temperature. The best comonomer for the sorption of 1 is methacrylamide. Concentration enhancements of up to approximately 200-fold are obtainable, and are proposed to account for previously observed rate accelerations in catalyst-containing porous polymers. Partition efficiency (PE) measurements, described as the ratio of polymer to original solution concentrations, are presented for a variety of organic compounds. The PE is sensitive to analyte structure and ranges from 1 to 170 (180 being the maximum under the conditions employed), with linear alkanes at the low end of the spectrum and polar functional groups at the opposite.

Citations

Aug 10, 2006·Dalton Transactions : an International Journal of Inorganic Chemistry·Alexander SchillerKay Severin
Sep 10, 2009·Chemistry, an Asian Journal·Minsul JangMakoto Fujita
Nov 13, 2013·Chemical Communications : Chem Comm·Shunsheng CaoAnthony P F Turner

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