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Phosphonium Boranes for the Selective Transport of Fluoride Anions across Artificial Phospholipid Membranes
Author(s) -
Park Gyeongjin,
Gabbaï François P.
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201914958
Subject(s) - phosphonium , chemistry , fluoride , boranes , lipophilicity , tetraphenylborate , membrane , tetracoordinate , steric effects , vesicle , ion , inorganic chemistry , medicinal chemistry , organic chemistry , boron , computer graphics (images) , computer science , planar , biochemistry
Abstract With the view of developing selective transmembrane anion transporters, a series of phosphonium boranes of general formula [ p ‐RPh 2 P(C 6 H 4 )BMes 2 ] + have been synthesized and evaluated. The results demonstrate that variation of the R group appended to the phosphorus atom informs the lipophilicity of these compounds, their Lewis acidity, as well as their transport activity. Anion transport experiments in POPC‐based large unilamellar vesicles show that these main‐group cations are highly selective for the fluoride anion, which is transported more than 20 times faster than the chloride anion. Finally, this work shows that the anion transport properties of these compounds are extremely sensitive to the steric crowding about the boron atom, pointing to the crucial involvement of the Group 13 element as the anion binding site.