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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...
Autores principales: | , , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2021
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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. |
format | Online Article Text |
id | pubmed-8293821 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
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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