Anion Responsive Molecular Switch Based on a Doubly‐Strapped Calixpyrrole
Helttunen, K. (2022). Anion Responsive Molecular Switch Based on a Doubly‐Strapped Calixpyrrole. European Journal of Organic Chemistry, 2022(42), Article e202200647. https://doi.org/10.1002/ejoc.202200647
Published inEuropean Journal of Organic Chemistry
© 2022 The Authors. European Journal of Organic Chemistry published by Wiley-VCH GmbH.
A calixpyrrole receptor bearing two proximally meso - meso linking isophthaloyl straps displays open and closed states depending on the calixpyrrole conformation. In the crystal structures and in non-polar solvent, the calixpyrrole adopts open 1,3-alternate conformation with straps on the sides. Anion binding triggers a closed state of the receptor providing two types of interactions with an aromatic benzoate guest: hydrogen bonds from the pyrrolic groups and π ··· π interactions from the phenyl groups of the straps. Slow exchange dynamics was observed on the NMR timescale indicating that benzoate, acetate and chloride anions, which bind with relatively low affinity get kinetically trapped in the receptor as insects in a Venus flytrap .
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Related funder(s)Academy of Finland
Funding program(s)Academy Research Fellow, AoF; Research costs of Academy Research Fellow, AoF
Additional information about fundingAcademy of Finland is acknowledged for financial support (projects 309910, 314287, and 335685).
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