Anion binding properties of 5,5′-dicarboxamido-dipyrrolylmethanes

Abstract

A series of 5,5'-dicarboxamido-dipyrrolylmethanes have been synthesized and in some cases crystallographically characterized. Proton NMR titrations have revealed that these compounds, that contain only four neutral hydrogen bond donors and are acyclic, selectively bind anions in very competitive solvent media such as DMSO-d6/water mixtures.

Artificial Receptors for the Recognition of Phosphorylated Molecules

“…However, analysis in 25% water in DMSO allowed a binding constant of 2.34 × 10 2 M –1 to be determined. The chemically more stable dimethyl-substituted dipyrrolylmethane receptors 402 displayed similar selectivities but was characterized by reduced binding constants as compared to receptor 401 . Proton NMR spectroscopy and computational studies of these receptors supported a linear binding cleft with hydrogen bonds between one phosphate oxygen atom and both the pyrrole and amide hydrogen atoms on each side of the receptor.…”

Anion Recognition Strategies Based on Combined Noncovalent Interactions

“…Optimized structure of the complex 151 ·H 2 PO 4 – by DFT calculation using Spartan ’02. Reprinted with permission from ref . Copyright 2004 Royal Society of Chemistry.…”

“…In the same context, the (5,5′-dicarboxamidodipyrrolyl)methane skeleton 137 of the receptors 147−152 (Figure 112) was explored as a binding core for the recognition of anions in DMSO/D 2 O (5%).…”

Synthesis and Anion Binding Properties of 2,5-Diamidothiophene Polypyrrole Schiff Base Macrocycles

“…In an effort to understand more completely the determinants of this selectivity, we have sought to replace the central 2,6-diamidopyrridine moiety by another known anion receptor subunit, namely, 2,5-diamidothiophene . Such a substitution was expected to result in a more flexible macrocyclic receptor and one that would interact with a wider range of anions …”