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Supramolecular packing of alkyl substituted Janus face all-cis 2,3,4,5,6-pentafluorocyclohexyl motifs

This study uses X-ray crystallography, theory and Langmuir isotherm analysis to explore the conformations and molecular packing of alkyl all-cis 2,3,4,5,6-pentafluorocyclohexyl motifs, which are prepared by direct aryl hydrogenations from alkyl- or vinyl-pentafluoroaryl benzenes. Favoured conformati...

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Autores principales: Clark, Joshua L., Taylor, Alaric, Geddis, Ailsa, Neyyappadath, Rifahath M., Piscelli, Bruno A., Yu, Cihang, Cordes, David B., Slawin, Alexandra M. Z., Cormanich, Rodrigo A., Guldin, Stefan, O'Hagan, David
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8293821/
https://www.ncbi.nlm.nih.gov/pubmed/34349942
http://dx.doi.org/10.1039/d1sc02130c
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author Clark, Joshua L.
Taylor, Alaric
Geddis, Ailsa
Neyyappadath, Rifahath M.
Piscelli, Bruno A.
Yu, Cihang
Cordes, David B.
Slawin, Alexandra M. Z.
Cormanich, Rodrigo A.
Guldin, Stefan
O'Hagan, David
author_facet Clark, Joshua L.
Taylor, Alaric
Geddis, Ailsa
Neyyappadath, Rifahath M.
Piscelli, Bruno A.
Yu, Cihang
Cordes, David B.
Slawin, Alexandra M. Z.
Cormanich, Rodrigo A.
Guldin, Stefan
O'Hagan, David
author_sort Clark, Joshua L.
collection PubMed
description This study uses X-ray crystallography, theory and Langmuir isotherm analysis to explore the conformations and molecular packing of alkyl all-cis 2,3,4,5,6-pentafluorocyclohexyl motifs, which are prepared by direct aryl hydrogenations from alkyl- or vinyl-pentafluoroaryl benzenes. Favoured conformations retain the more polar triaxial C–F bond arrangement of the all-cis 2,3,4,5,6-pentafluorocyclohexyl ring systems with the alkyl substituent adopting an equatorial orientation, and accommodating strong supramolecular interactions between rings. Langmuir isotherm analysis on a water subphase of a long chain fatty acid and alcohol carrying terminal all-cis 2,3,4,5,6-pentafluorocyclohexyl rings do not show any indication of monolayer assembly relative to their cyclohexane analogues, instead the molecules appear to aggregate and form higher molecular assemblies prior to compression. The study indicates the power and potential of this ring system as a motif for ordering supramolecular assembly.
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spelling pubmed-82938212021-08-03 Supramolecular packing of alkyl substituted Janus face all-cis 2,3,4,5,6-pentafluorocyclohexyl motifs Clark, Joshua L. Taylor, Alaric Geddis, Ailsa Neyyappadath, Rifahath M. Piscelli, Bruno A. Yu, Cihang Cordes, David B. Slawin, Alexandra M. Z. Cormanich, Rodrigo A. Guldin, Stefan O'Hagan, David Chem Sci Chemistry This study uses X-ray crystallography, theory and Langmuir isotherm analysis to explore the conformations and molecular packing of alkyl all-cis 2,3,4,5,6-pentafluorocyclohexyl motifs, which are prepared by direct aryl hydrogenations from alkyl- or vinyl-pentafluoroaryl benzenes. Favoured conformations retain the more polar triaxial C–F bond arrangement of the all-cis 2,3,4,5,6-pentafluorocyclohexyl ring systems with the alkyl substituent adopting an equatorial orientation, and accommodating strong supramolecular interactions between rings. Langmuir isotherm analysis on a water subphase of a long chain fatty acid and alcohol carrying terminal all-cis 2,3,4,5,6-pentafluorocyclohexyl rings do not show any indication of monolayer assembly relative to their cyclohexane analogues, instead the molecules appear to aggregate and form higher molecular assemblies prior to compression. The study indicates the power and potential of this ring system as a motif for ordering supramolecular assembly. The Royal Society of Chemistry 2021-06-04 /pmc/articles/PMC8293821/ /pubmed/34349942 http://dx.doi.org/10.1039/d1sc02130c Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Clark, Joshua L.
Taylor, Alaric
Geddis, Ailsa
Neyyappadath, Rifahath M.
Piscelli, Bruno A.
Yu, Cihang
Cordes, David B.
Slawin, Alexandra M. Z.
Cormanich, Rodrigo A.
Guldin, Stefan
O'Hagan, David
Supramolecular packing of alkyl substituted Janus face all-cis 2,3,4,5,6-pentafluorocyclohexyl motifs
title Supramolecular packing of alkyl substituted Janus face all-cis 2,3,4,5,6-pentafluorocyclohexyl motifs
title_full Supramolecular packing of alkyl substituted Janus face all-cis 2,3,4,5,6-pentafluorocyclohexyl motifs
title_fullStr Supramolecular packing of alkyl substituted Janus face all-cis 2,3,4,5,6-pentafluorocyclohexyl motifs
title_full_unstemmed Supramolecular packing of alkyl substituted Janus face all-cis 2,3,4,5,6-pentafluorocyclohexyl motifs
title_short Supramolecular packing of alkyl substituted Janus face all-cis 2,3,4,5,6-pentafluorocyclohexyl motifs
title_sort supramolecular packing of alkyl substituted janus face all-cis 2,3,4,5,6-pentafluorocyclohexyl motifs
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8293821/
https://www.ncbi.nlm.nih.gov/pubmed/34349942
http://dx.doi.org/10.1039/d1sc02130c
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