A1 Journal article (refereed)
Anion Responsive Molecular Switch Based on a Doubly‐Strapped Calix[4]pyrrole (2022)

Helttunen, K. (2022). Anion Responsive Molecular Switch Based on a Doubly‐Strapped Calix[4]pyrrole. European Journal of Organic Chemistry, 2022(42), Article e202200647. https://doi.org/10.1002/ejoc.202200647

JYU authors or editors

Publication details

All authors or editors: Helttunen, Kaisa

Journal or series: European Journal of Organic Chemistry

ISSN: 1434-193X

eISSN: 1099-0690

Publication year: 2022

Publication date: 15/08/2022

Volume: 2022

Issue number: 42

Article number: e202200647

Publisher: Wiley-VCH Verlag

Publication country: Germany

Publication language: English

DOI: https://doi.org/10.1002/ejoc.202200647

Publication open access: Openly available

Publication channel open access: Partially open access channel

Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/83896

Abstract

A calix[4]pyrrole receptor bearing two proximally meso - meso linking isophthaloyl straps displays open and closed states depending on the calix[4]pyrrole conformation. In the crystal structures and in non-polar solvent, the calix[4]pyrrole 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 .

Keywords: heterocyclic compounds; chemical bonds; hydrogen bonds; anions; supramolecular chemistry; NMR spectroscopy

Free keywords: anions; calix[4]pyrroles; molecular switch; NMR spectroscopy; supramolecular chemistry

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Ministry reporting: Yes

VIRTA submission year: 2022

JUFO rating: 1