Supramolecular packing of alkyl substituted Janus face all-cis 2,3,4,5,6-pentafluorocyclohexyl motifs
Autor: | David O'Hagan, David B. Cordes, Stefan Guldin, Alaric Taylor, Joshua Clark, Ailsa Geddis, Rodrigo A. Cormanich, Bruno Piscelli, Cihang Yu, Rifahath M. Neyyappadath, Alexandra M. Z. Slawin |
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Přispěvatelé: | EPSRC, University of St Andrews. School of Chemistry, University of St Andrews. EaSTCHEM, University of St Andrews. Biomedical Sciences Research Complex |
Rok vydání: | 2021 |
Předmět: |
chemistry.chemical_classification
Aryl technology industry and agriculture Supramolecular chemistry Substituent DAS General Chemistry QD Chemistry Ring (chemistry) Supramolecular assembly chemistry.chemical_compound Crystallography chemistry Monolayer Molecule QD lipids (amino acids peptides and proteins) Alkyl |
Zdroj: | Chemical Science. 12:9712-9719 |
ISSN: | 2041-6539 2041-6520 |
DOI: | 10.1039/d1sc02130c |
Popis: | We thank EPSRC for a grant (EP/R013799/1) and for a Studentship (JC) through the CRITICAT Centre for Doctoral training (CDT). FAPESP is also gratefully acknowledged for a studentship (BAP, #2019/03855-3), and a Young Research Award (RAC, #2018/03910-1). CENAPAD-SP, CESUP and SDumont are acknowledged for computational clusters used in theory calculations. 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. Publisher PDF |
Databáze: | OpenAIRE |
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