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Fluorinated Tetraphosphonate Cavitands.

Alessandro Pedrini1, Federico Bertani2, Enrico Dalcanale3

  • 1Department of Chemistry, Life Sciences and Environmental Sustainability, University of Parma, Parco Area delle Scienze 17/A, 43124 Parma, Italy. alessandro.pedrini@studenti.unipr.it.

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Summary
This summary is machine-generated.

Two novel synthetic routes introduce fluorine into resorcinarene cavitands. Cavitand 2 shows significant NMR shifts upon complexation, indicating cation-dipole and H-bonding interactions with guests.

Keywords:
fluorinemolecular probemolecular recognitionphosphonate cavitandssarcosine methyl ester

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Area of Science:

  • Supramolecular Chemistry
  • Organic Synthesis
  • Fluorine Chemistry

Background:

  • Resorcinarene-based cavitands are versatile molecular hosts.
  • Fluorinated compounds offer unique properties for molecular recognition.
  • Selective functionalization of cavitands is crucial for tailored applications.

Purpose of the Study:

  • To develop synthetic protocols for incorporating fluorine into resorcinarene cavitands.
  • To synthesize two distinct fluorinated cavitands (Cavitand 1 and Cavitand 2).
  • To investigate the complexation behavior of these cavitands with a model guest.

Main Methods:

  • Synthesis of fluorinated resorcinarene-based cavitands.
  • Nuclear Magnetic Resonance (NMR) titration experiments.
  • Analysis of 19F NMR spectral changes upon guest binding.

Main Results:

  • Successful synthesis of Cavitand 1 with fluorocarbon tails and Cavitand 2 with a para-fluorine substituent.
  • Cavitand 2 exhibited a noticeable downfield shift in its 19F NMR signal upon complexation.
  • No significant 19F NMR change was observed for Cavitand 1 upon complexation.

Conclusions:

  • The synthetic strategies enable the introduction of fluorine at different cavitand positions.
  • Cavitand 2's 19F NMR response highlights its ability to engage in specific interactions (cation-dipole, H-bonding) with guests.
  • Fluorine NMR can serve as a sensitive probe for studying host-guest interactions in functionalized cavitands.