Issue 31, 2020

Capture and displacement-based release of the bicarbonate anion by calix[4]pyrroles with small rigid straps

Abstract

Two-phenoxy walled calix[4]pyrroles 1 and 2 strapped with small rigid linkers containing pyridine and benzene, respectively, have been synthesized. 1H NMR spectroscopic analyses carried out in CDCl3 revealed that both of receptors 1 and 2 recognize only F and HCO3 among various test anions with high preference for HCO3 (as the tetraethylammonium, TEA+ salt) relative to F (as the TBA+ salt). The bound HCO3 anion was completely released out of the receptors upon the addition of F (as the tetrabutylammonium, TBA+ salt) as a result of significantly enhanced affinities and selectivities of the receptors for F once converted to the TEAHCO3 complexes. Consequently, relatively stable TEAF complexes of receptors 1 and 2 were formed via anion metathesis occurring within the receptor cavities. By contrast, the direct addition of TEAF to receptors 1 and 2 produces different complexation products initially, although eventually the same TEAF complexes are produced as via sequential TEAHCO3 and TBAF addition. These findings are rationalized in terms of the formation of different ion pair complexes involving interactions both inside and outside of the core receptor framework.

Graphical abstract: Capture and displacement-based release of the bicarbonate anion by calix[4]pyrroles with small rigid straps

Supplementary files

Article information

Article type
Edge Article
Submitted
21 Jun 2020
Accepted
24 Jul 2020
First published
24 Jul 2020
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2020,11, 8288-8294

Capture and displacement-based release of the bicarbonate anion by calix[4]pyrroles with small rigid straps

N. J. Heo, J. H. Yang, V. M. Lynch, B. J. Ko, J. L. Sessler and S. K. Kim, Chem. Sci., 2020, 11, 8288 DOI: 10.1039/D0SC03445B

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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