Enantiorecognition of a chiral analyte usually requiresthe abilityto respond with high specificity to one of the two enantiomers ofa chiral compound. However, in most cases, chiral sensors have chemicalsensitivity toward both enantiomers, showing differences only in theintensity of responses. Furthermore, specific chiral receptors areobtained with high synthetic efforts and have limited structural versatility.These facts hinder the implementation of chiral sensors in many potentialapplications. Here, we utilize the presence of both enantiomers ofeach receptor to introduce a novel normalization that allows the enantio-recognitionof compounds even when single sensors are not specific for one enantiomerof a target analyte. For this purpose, a novel protocol that permitsthe fabrication of a large set of enantiomeric receptor pairs withlow synthetic efforts by combining metalloporphyrins with (R,R)- and (S,S)-cyclohexanohemicucurbit[8]uril is developed. The potentialitiesof this approach are investigated by an array of four pairs of enantiomericsensors fabricated using quartz microbalances since gravimetric sensorsare intrinsically non-selective toward the mechanism of interactionof analytes and receptors. Albeit the weak enantioselectivity of singlesensors toward limonene and 1-phenylethylamine, the normalizationallows the correct identification of these enantiomers in the vaporphase indifferent to their concentration. Remarkably, the achiralmetalloporphyrin choice influences the enantioselective properties,opening the way to easily obtain a large library of chiral receptorsthat can be implemented in actual sensor arrays. These enantioselectiveelectronic noses and tongues may have a potential striking impactin many medical, agrochemical, and environmental fields.

Chiral Recognition by Supramolecular Porphyrin–Hemicucurbit[8]uril-Functionalized Gravimetric Sensors

Gabriele Giancane;Simona Bettini;Ludovico Valli;
2023-01-01

Abstract

Enantiorecognition of a chiral analyte usually requiresthe abilityto respond with high specificity to one of the two enantiomers ofa chiral compound. However, in most cases, chiral sensors have chemicalsensitivity toward both enantiomers, showing differences only in theintensity of responses. Furthermore, specific chiral receptors areobtained with high synthetic efforts and have limited structural versatility.These facts hinder the implementation of chiral sensors in many potentialapplications. Here, we utilize the presence of both enantiomers ofeach receptor to introduce a novel normalization that allows the enantio-recognitionof compounds even when single sensors are not specific for one enantiomerof a target analyte. For this purpose, a novel protocol that permitsthe fabrication of a large set of enantiomeric receptor pairs withlow synthetic efforts by combining metalloporphyrins with (R,R)- and (S,S)-cyclohexanohemicucurbit[8]uril is developed. The potentialitiesof this approach are investigated by an array of four pairs of enantiomericsensors fabricated using quartz microbalances since gravimetric sensorsare intrinsically non-selective toward the mechanism of interactionof analytes and receptors. Albeit the weak enantioselectivity of singlesensors toward limonene and 1-phenylethylamine, the normalizationallows the correct identification of these enantiomers in the vaporphase indifferent to their concentration. Remarkably, the achiralmetalloporphyrin choice influences the enantioselective properties,opening the way to easily obtain a large library of chiral receptorsthat can be implemented in actual sensor arrays. These enantioselectiveelectronic noses and tongues may have a potential striking impactin many medical, agrochemical, and environmental fields.
File in questo prodotto:
File Dimensione Formato  
2023_ACS Applied Mat and Int.pdf

non disponibili

Tipologia: Versione editoriale
Licenza: Copyright dell'editore
Dimensione 5.26 MB
Formato Adobe PDF
5.26 MB Adobe PDF   Visualizza/Apri   Richiedi una copia

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11587/497087
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus ND
  • ???jsp.display-item.citation.isi??? 3
social impact