Jump to main content
Jump to site search


Efficient hydrogen bonding recognition in water using aryl-extended calix[4]pyrrole receptors

Author affiliations

Abstract

We describe the synthesis of four water-soluble aryl-extended calix[4]pyrrole receptors and report their binding properties with multiple neutral polar guests in water. The prepared receptors present different functionalization at their upper rims and have in common the placement of water solubilizing pyridinium groups at their lower rims. We investigate the interaction of the receptors with a guest series in water solution using 1H NMR titrations and ITC experiments. Despite the known competitive nature of water for hydrogen-bonding interactions, we demonstrate the formation of thermodynamically highly stable 1 : 1 inclusion complexes stabilized by hydrogen-bonding interactions. We show that increasing the hydrogen-bond acceptor character of the guest has a positive impact on binding affinity. This result suggests that the receptor's cavity is indeed a better hydrogen-bond donor to interact with the guests than water molecules. We also assess the important contribution of the hydrophobic effect to binding by comparing the binding affinities of analogous inclusion complexes in water and chloroform solutions. The more polar guests are bound with similar affinities in the two solvents. We compare the binding properties of the different complexes in order to derive general trends.

Graphical abstract: Efficient hydrogen bonding recognition in water using aryl-extended calix[4]pyrrole receptors

Back to tab navigation

Supplementary files

Publication details

The article was received on 12 Nov 2018, accepted on 19 Dec 2018 and first published on 21 Dec 2018


Article type: Edge Article
DOI: 10.1039/C8SC05034A
Citation: Chem. Sci., 2019, Advance Article
  • Open access: Creative Commons BY-NC license
  •   Request permissions

    Efficient hydrogen bonding recognition in water using aryl-extended calix[4]pyrrole receptors

    G. Peñuelas-Haro and P. Ballester, Chem. Sci., 2019, Advance Article , DOI: 10.1039/C8SC05034A

    This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material and it is not used for commercial purposes.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
    • For reproduction of material from PCCP:
      [Original citation] - Published by the PCCP Owner Societies.
    • For reproduction of material from PPS:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
    • For reproduction of material from all other RSC journals:
      [Original citation] - Published by The Royal Society of Chemistry.

    Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Search articles by author

Spotlight

Advertisements