Issue 3, 2020
From the journal:

Organic Chemistry Frontiers

Phenanthroline-strapped calix[4]pyrroles: anion receptors displaying affinity reversal as a function of solvent polarity†

Nam Jung Heo,‡a   Ju Hyun Oh,‡a   Jeong Tae Lee,b   Qing He, ORCID logo *c   Jonathan L. Sessler ORCID logo *d  and  Sung Kuk Kim ORCID logo *a  

* Corresponding authors

a Department of Chemistry and Research Institute of Natural Science, Gyeongsang National University, Jinju 52828, Korea
E-mail: sungkukkim@gnu.ac.kr

b Department of Chemistry and Institute of Applied Chemistry, Hallym University, Chuncheon 24252, Korea

c State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. China
E-mail: heqing85@hnu.edu.cn

d Department of Chemistry, The University of Texas at Austin, 105 E. 24th Street-Stop A5300, Austin, Texas 78712-1224, USA
E-mail: sessler@cm.utexas.edu

Abstract

Calix[4]pyrroles 1 and 2, diametrically strapped with a phenanthroline via ester and amide linkages, respectively, have been synthesized as anion receptors. It was revealed by 1H NMR spectroscopic analysis that receptors 1 and 2 possessing both hydrogen bonding donors and acceptors were able to bind the bicarbonate anion (as its tetraethylammonium (TEA+) or sodium salt) in CDCl3, as well as in 15% aqueous DMSO with high affinity and selectivity over other anions. The amide-based receptor 2 contains additional potential hydrogen bonding donors relative to its ester-based congener 1. Nevertheless, in CDCl3 receptor 1 was found to display a higher affinity for all test anions than receptor 2. In contrast, in 15% aqueous DMSO solution the affinities of receptor 2 for anions, in particular chloride, bicarbonate, and dihydrogen phosphate, were enhanced, whereas those of receptor 1 were reduced dramatically with no appreciable interaction being seen in the case of most test anions considered in this study. These reversals in selectivity and affinities underscore the importance of solvent in regulating the recognition features of seemingly similiar anion binding agents.

Graphical abstract: Phenanthroline-strapped calix[4]pyrroles: anion receptors displaying affinity reversal as a function of solvent polarity

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Article information

DOI
https://doi.org/10.1039/C9QO01377F
Article type
Research Article
Submitted
16 Nov 2019
Accepted
31 Dec 2019
First published
02 Jan 2020

Org. Chem. Front., 2020,7, 548-556

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Phenanthroline-strapped calix[4]pyrroles: anion receptors displaying affinity reversal as a function of solvent polarity

N. J. Heo, J. H. Oh, J. T. Lee, Q. He, J. L. Sessler and S. K. Kim, Org. Chem. Front., 2020, 7, 548 DOI: 10.1039/C9QO01377F

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