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

Reut Shapira; Sapir Katalan; Rachel Edrei; Yoav Eichen

doi:https://doi.org/10.1039/d0ra07643k

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

Reut Shapira, Sapir Katalan, Rachel Edrei, Yoav Eichen

Technion - Israel Institute of Technology

Research output: Contribution to journal › Article › peer-review

Abstract

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.

Original language	English
Pages (from-to)	39195-39203
Number of pages	9
Journal	RSC Advances
Volume	10
Issue number	64
DOIs	https://doi.org/10.1039/d0ra07643k
State	Published - 26 Oct 2020

All Science Journal Classification (ASJC) codes

Chemistry(all)
Chemical Engineering(all)

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

abstract = "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.",

author = "Reut Shapira and Sapir Katalan and Rachel Edrei and Yoav Eichen",

note = "Publisher Copyright: {\textcopyright} The Royal Society of Chemistry.",

year = "2020",

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doi = "https://doi.org/10.1039/d0ra07643k",

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T1 - Chirality dependent inverse-melting and re-entrant gelation in α-cyclodextrin/1-phenylethylamine mixtures

AU - Shapira, Reut

AU - Katalan, Sapir

AU - Edrei, Rachel

AU - Eichen, Yoav

PY - 2020/10/26

Y1 - 2020/10/26

N2 - 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.

AB - 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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U2 - https://doi.org/10.1039/d0ra07643k

DO - https://doi.org/10.1039/d0ra07643k

M3 - مقالة

SN - 2046-2069

VL - 10

SP - 39195

EP - 39203

JO - RSC Advances

JF - RSC Advances

IS - 64

ER -

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

Abstract

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