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Fluorinated Tetraphosphonate Cavitands.

ABSTRACT: Two synthetic protocols for the introduction of fluorine atoms into resorcinarene-based cavitands, at the lower and upper rim, respectively, are reported. Cavitand 1, bearing four fluorocarbon tails, and cavitand 2, which presents a fluorine atom on the para position of a diester phosphonate phenyl substituent, were synthesized and their complexation abilities toward the model guest sarcosine methyl ester hydrochloride were evaluated via NMR titration experiments. The effect of complexation on the ¹⁹F NMR resonance of the probe is evident only in the case of cavitand 2, where the inset of the cation-dipole and H-bonding interactions between the P=O bridges and the guest is reflected in a sizable downfield shift of the fluorine probe.

SUBMITTER: Pedrini A

PROVIDER: S-EPMC6222714 | biostudies-literature | 2018 Oct

REPOSITORIES: biostudies-literature

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Fluorinated Tetraphosphonate Cavitands.

Pedrini Alessandro A Bertani Federico F Dalcanale Enrico E

Molecules (Basel, Switzerland) 20181017 10

Two synthetic protocols for the introduction of fluorine atoms into resorcinarene-based cavitands, at the lower and upper rim, respectively, are reported. Cavitand 1, bearing four fluorocarbon tails, and cavitand 2, which presents a fluorine atom on the para position of a diester phosphonate phenyl substituent, were synthesized and their complexation abilities toward the model guest sarcosine methyl ester hydrochloride were evaluated via NMR titration experiments. The effect ...[more]

PMID: 30336589

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