Selective Anion Sensing by Chiral Macrocyclic Receptors with Multiple Hydrogen-Bonding Sites

Abstract

Chiral macrocycles featuring sulfonamide and/or amide groups as anion-binding sites were synthesized. X-ray crystal structures and DFT calculations have shown that they adopt different conformations that may lead to unique binding behavior. Indeed, various anions could be sensed by their colorimetric and/or fluorescence signal output. The chiral macrocycles showed chiral recognition for chiral anions. Furthermore, a multisensor array with two or four chiral receptors discriminated seven phosphate anions (AMP, ADP, ATP, CMP, GMP, Pi, and PPi) with 100% classification accuracy.

Sensitive water-soluble fluorescent chemosensor for chloride based on a bisquinolinium pyridine-dicarboxamide compound

“…Crystallographic results for 1 show that amide groups are converged and coplanar with the central pyridine ring, this conformation is usually observed for the fragment of pyridine-2,6-dicarboxamide of both macrocyclic and acyclic receptors as a result of intramolecular hydrogen bonding interactions between pyridine nitrogen and NH amide groups (Ema et al, 2014;Wagner-Wysiecka and Chojnaki, 2012). The distances NH … HN and 2CH … HC2 of 1 are 3.006 Å and 3.994 Å, respectively.…”

Pyrene Derivative Emitting Red or near-Infrared Light with Monomer/Excimer Conversion and Its Application to Ratiometric Detection of Hypochlorite

“…[1][2][3][4][5][6][7] To a large extent, an excellent sensing system depends on the nature of chromophores themselves. Therefore, it's essential for fluorophores to have a good luminescent property, and the development of new fluorophores with satisfactory photophysical properties is highly desirable.…”

Dithieno[3,2-a:2′,3′-c]phenazine-based chemical probe for anions: a spectroscopic study of binding

“…We 29,30 and others [31][32][33][34][35] have reported the use of sulfonamide groups to detect a wide range of anions. In this paper, we report on the preparation of the compound N,N'- (2,5-…”