Anthracene‐Based Amido−Amine Cage Receptor for Anion Recognition under Neutral Aqueous Conditions

Abstract

A new amido−amine cage receptor, which combines 1,8‐anthracene diacarboxamide subunit and a polyammonium azamacrocycle, is reported. Bearing both the hydrogen bond donor and the acceptor binding sites, the receptor is able to bind phosphate selectively under neutral (pH 7.2) aqueous conditions. The recognition events for phosphate and dicarboxylates are accomplished by a fluorescence enhancement in the anthracene emission. As revealed by experimental and theoretical studies, phosphate and oxalate show different recognition modes. Phosphate demonstrates hydrogen bond acceptor properties, while the coordination of oxalate favours the protonation of the receptor.

One-Pot Parallel Synthesis of Unclosed Cryptands—Searching for Selective Anion Receptors via Static Combinatorial Chemistry Techniques

“…Targeted recognition of phosphates is constantly being researched intensively. 17 Macrocyclic receptors, such as UCs, due to their structure, are perfectly geared toward recognizing phosphates. In order to determine the affinity of the receptors for anions, we decided to use the titration technique controlled by 1 H NMR spectrometry.…”

“…Targeted recognition of phosphates is constantly being researched intensively . Macrocyclic receptors, such as UCs, due to their structure, are perfectly geared toward recognizing phosphates.…”

The Role of Hydrazine in Colorimetric Probes Based on Ferrocene Derivative

“…The interaction sites are usually À NH, À OH, À SH groups, which often take part in the design of anion receptors. [21][22][23][24][25][26] Hydrazine can strongly bind anions through double hydrogen bond interactions and is used to design neutral receptors for anion recognition. [27,28] Because ferrocene has high thermal stability, high tolerance, rigid skeleton and planar chirality, ferrocene and its derivatives have a wide range of research and applications in antibacterial, anticancer, luminescent materials, chemical sensing, ion recognition, biocatalysis and so on.…”

“…The two pieces are usually linked with covalent or non‐covalent bonds. The interaction sites are usually −NH, −OH, −SH groups, which often take part in the design of anion receptors [21–26] . Hydrazine can strongly bind anions through double hydrogen bond interactions and is used to design neutral receptors for anion recognition [27,28] .…”

Helix-Like Receptors for Perrhenate Recognition Forming Hydrogen Bonds with All Four Oxygen Atoms

“…Anions play a significant role in living systems. The design of artificial anion receptors is a challenge in supramolecular chemistry that has received great attention in recent years [1][2][3][4][5][6], moving from being an entirely fundamental area of supramolecular chemistry to a range of applications. Perrhenate (ReO 4 − ) and pertechnetate (TcO 4 − ) are considered to be the anions that are among the most "difficult to bind" due to their relatively large size and low charge density [7,8].…”