Chirality dependent inverse-melting and re-entrant gelation in α-cyclodextrin/1-phenylethylamine mixtures

Solutions of cyclohexakis-(1→4)-α-d-glucopyranosyl, α-cyclodextrin, αCD, in R-(+)-1-phenylethylamine, αCD/R-PEA, and S-(−)-1-phenylethylamine, αCD/S-PEA, display abnormal phase transitions that strongly depend on supramolecular diastereomeric interactions. While αCD/R-PEA mixtures show one sol–gel i...

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Autores principales: Shapira, Reut, Katalan, Sapir, Edrei, Rachel, Eichen, Yoav
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9057694/
https://www.ncbi.nlm.nih.gov/pubmed/35518437
http://dx.doi.org/10.1039/d0ra07643k
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author Shapira, Reut
Katalan, Sapir
Edrei, Rachel
Eichen, Yoav
author_facet Shapira, Reut
Katalan, Sapir
Edrei, Rachel
Eichen, Yoav
author_sort Shapira, Reut
collection PubMed
description Solutions of cyclohexakis-(1→4)-α-d-glucopyranosyl, α-cyclodextrin, αCD, in R-(+)-1-phenylethylamine, αCD/R-PEA, and S-(−)-1-phenylethylamine, αCD/S-PEA, display abnormal phase transitions that strongly depend on supramolecular diastereomeric interactions. While αCD/R-PEA mixtures show one sol–gel inverse-melting phase transition, αCD/S-PEA mixtures show temperature dependent gel–sol–gel re-entrant behavior. NMR, Raman spectroscopy, microscopy and X-ray scattering measurements reveal that hydrogen bond weakening in solution, as well as changes in crystal composition are responsible for entropy increase and gel formation upon heating.
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spelling pubmed-90576942022-05-04 Chirality dependent inverse-melting and re-entrant gelation in α-cyclodextrin/1-phenylethylamine mixtures Shapira, Reut Katalan, Sapir Edrei, Rachel Eichen, Yoav RSC Adv Chemistry Solutions of cyclohexakis-(1→4)-α-d-glucopyranosyl, α-cyclodextrin, αCD, in R-(+)-1-phenylethylamine, αCD/R-PEA, and S-(−)-1-phenylethylamine, αCD/S-PEA, display abnormal phase transitions that strongly depend on supramolecular diastereomeric interactions. While αCD/R-PEA mixtures show one sol–gel inverse-melting phase transition, αCD/S-PEA mixtures show temperature dependent gel–sol–gel re-entrant behavior. NMR, Raman spectroscopy, microscopy and X-ray scattering measurements reveal that hydrogen bond weakening in solution, as well as changes in crystal composition are responsible for entropy increase and gel formation upon heating. The Royal Society of Chemistry 2020-10-26 /pmc/articles/PMC9057694/ /pubmed/35518437 http://dx.doi.org/10.1039/d0ra07643k Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Shapira, Reut
Katalan, Sapir
Edrei, Rachel
Eichen, Yoav
Chirality dependent inverse-melting and re-entrant gelation in α-cyclodextrin/1-phenylethylamine mixtures
title Chirality dependent inverse-melting and re-entrant gelation in α-cyclodextrin/1-phenylethylamine mixtures
title_full Chirality dependent inverse-melting and re-entrant gelation in α-cyclodextrin/1-phenylethylamine mixtures
title_fullStr Chirality dependent inverse-melting and re-entrant gelation in α-cyclodextrin/1-phenylethylamine mixtures
title_full_unstemmed Chirality dependent inverse-melting and re-entrant gelation in α-cyclodextrin/1-phenylethylamine mixtures
title_short Chirality dependent inverse-melting and re-entrant gelation in α-cyclodextrin/1-phenylethylamine mixtures
title_sort chirality dependent inverse-melting and re-entrant gelation in α-cyclodextrin/1-phenylethylamine mixtures
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9057694/
https://www.ncbi.nlm.nih.gov/pubmed/35518437
http://dx.doi.org/10.1039/d0ra07643k
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AT edreirachel chiralitydependentinversemeltingandreentrantgelationinacyclodextrin1phenylethylaminemixtures
AT eichenyoav chiralitydependentinversemeltingandreentrantgelationinacyclodextrin1phenylethylaminemixtures

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