Abstract
The use of the 3,4-difluoro-1H-pyrrole as a building block for the preparation of octamethyloctafluorocalix[4]pyrrole and 2,3-di(3‘,4‘-difluoropyrrol-2‘yl)quinoxaline is described. These latter two entities act as neutral anion receptors and were found to bind anions such as fluoride, chloride, or dihydrogen phosphate with an enhanced affinity compared to their non-fluorinated congeners as judged from 1H NMR, 19F NMR, and fluorescence emission spectroscopic analyses. The increase in affinity was especially high in case of chloride and dihydrogen phosphate anion, with the 2,3-di(3‘,4‘-difluoropyrrol-2‘-yl)quinoxaline system, in particular, displaying an affinity for H2PO4- that was improved by 3 orders of magnitude as compared to its non-fluorinated congener. This improvement in the affinity for the dihydrogen phosphate is accompanied by change of color from pale yellow to orange, thus allowing the use of such compounds as naked-eye sensors for phosphate anion. In the case of the octafluorocalix[4]pyrrole ...
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