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Summary

Aromatic oligoamides H8 and H16 form stable complexes with dicationic guests like octyl viologen (OV2+). The longer H16 exhibits higher affinity and negative cooperativity, selectively binding OV2+ over TB2+ in a novel host-guest system.

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Area of Science:

  • Supramolecular chemistry
  • Host-guest chemistry
  • Organic chemistry

Background:

  • Aromatic oligoamides can form stable helical structures with cavities.
  • Dicationic guests like octyl viologen (OV2+) and para-bis(trimethylammonium)benzene (TB2+) are of interest for complexation studies.

Purpose of the Study:

  • To investigate the complexation behavior of aromatic oligoamides H8 and H16 with dicationic guests OV2+ and TB2+.
  • To characterize the binding affinity, stoichiometry, and structural features of the resulting host-guest complexes.

Main Methods:

  • 1D and 2D 1H NMR spectroscopy
  • Isothermal titration calorimetry (ITC)
  • X-ray crystallography

Main Results:

  • H8 and H16 form 2:2 and 1:2 complexes with OV2+, respectively, with H16 showing higher binding affinity and negative cooperativity.
  • H16 binds TB2+ in a 1:1 ratio, demonstrating selectivity for OV2+ over TB2+.
  • The study revealed pairwise placement of repulsive OV2+ ions within the host cavity, adaptability between hosts and guests, and formation of stable pseudo-foldaxane structures.

Conclusions:

  • Aromatic oligoamides H8 and H16 effectively complex dicationic guests, forming stable pseudo-foldaxane structures.
  • The H16 host exhibits remarkable binding affinity, negative cooperativity, and selectivity, highlighting its potential in supramolecular chemistry.
  • This work presents a novel host-guest system with unique binding characteristics and structural motifs.