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

Heo, Nam Jung; Oh, Ju Hyun; Lee, Jeong Tae; He, Qing; Sessler, Jonathan L.; Kim, Sung Kuk

doi:10.1039/c9qo01377f

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

Journal Article · Thu Jan 02 00:00:00 EST 2020 · Organic Chemistry Frontiers (Online)

DOI:https://doi.org/10.1039/c9qo01377f· OSTI ID:1800009

Heo, Nam Jung ^[1]; Oh, Ju Hyun ^[1]; Lee, Jeong Tae ^[2];

^[3];

^[4];

^[1]

Gyeongsang National Univ., Jinju (Korea, Republic of). Dept. of Chemistry. Research Inst. of Natural Science
Hallym Univ., Chuncheon (Korea, Republic of). Dept. of Chemistry. Inst. of Applied Chemistry
Hunan Univ., Changsha (China). State Key Lab. of Chemo/Biosensing and Chemometrics. College of Chemistry and Chemical Engineering
Univ. of Texas, Austin, TX (United States). Dept. of Chemistry

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.

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Research Organization:: Univ. of Texas, Austin, TX (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: FG02-01ER15186

OSTI ID:: 1800009

Alternate ID(s):: OSTI ID: 1581835

Journal Information:: Organic Chemistry Frontiers (Online), Vol. 7, Issue 3; ISSN 2052-4129

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 8 works

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