Recognition of 1‐phenylethylamine enantiomers by thin solid films of inherently chiral calix[4]arene

Abstract

The enantiodiscrimination properties of stereomerically pure inherently chiral calix[4]arene acetic acids, as well as their esters and amides in relation to 1-phenylethylamine stereoisomers in liquid and gaseous phases were studied by means of proton magnetic resonance spectroscopy ( 1 H NMR) and quartz crystal microbalance (QCM) techniques. Series of QCM sensors with thin films of inherently chiral calix[4]arenes, immobilized on the quartz resonator surfaces by spin-coating and spreading drop methods have been fabricated. It was shown that sensors based on calix[4]arene acetic acids are able to recognize Rand S-forms of 1-phenylethylamine in gaseous phase under concentration level of 10-400 ppm.

Design of surface nanostructures for chirality sensing based on quartz crystal microbalance

“…To understand the chiral recognition between calixarenes and analytes, Zoya I. Kazantseva et al combined QCM and proton magnetic resonance spectroscopy ( 1 H NMR) techniques to study the complexation process of various chiral calix [4]arenes derivatives with gas-phase R/S-1-phenethylamine [78]. They proved that due to the acid-base interaction, only derivatives with acid could bind well with chiral amines.…”

Synthesis and separation of diastereomeric N‐(1‐phenylethyl)amides of inherently chiral hydroxydibenzoyloxy‐calix[4]arene acetic acids

“…Inherently chiral calixarenes with asymmetric arrangement of achiral substituents on a macrocyclic platform [1][2][3] are important compounds in the design of supramolecular host molecules, which have wide possibilities as enantioselective sensors, 4,5 chiral phases, 6,7 metalocomplex catalysts, and organocatalysts of asymmetric reactions. [8][9][10] Given the high and diverse biological activity of calixarenes, [11][12][13] they are also interesting building blocks for the synthesis of enantiomerically pure drugs.…”