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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

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

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Author(s):
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Clark, Joshua L. [1] ; Taylor, Alaric [2] ; Geddis, Ailsa [1] ; Neyyappadath, Rifahath M. [1] ; Piscelli, Bruno A. [3] ; Yu, Cihang [1] ; Cordes, David B. [1] ; Slawin, Alexandra M. Z. [1] ; Cormanich, Rodrigo A. [3] ; Guldin, Stefan [2] ; O'Hagan, David [1]
Total Authors: 11
Affiliation:
[1] Univ St Andrews, Sch Chem, St Andrews KY16 9ST, Fife - Scotland
[2] UCL, Dept Chem Engn, Torrington Pl, London WC1E 7JE - England
[3] Univ Estadual Campinas, Chem Inst, Monteiro Lobato St, BR-13083862 Campinas, SP - Brazil
Total Affiliations: 3
Document type: Journal article
Source: CHEMICAL SCIENCE; v. 12, n. 28, p. 9712-9719, JUL 28 2021.
Web of Science Citations: 1
Abstract

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. (AU)

FAPESP's process: 18/03910-1 - Physicochemical studies of fluorinated organic compounds: experimental and theoretical approaches
Grantee:Rodrigo Antonio Cormanich
Support Opportunities: Research Grants - Young Investigators Grants
FAPESP's process: 19/03855-3 - Synthesis of fluorinated derivatives of thymol and carvacrol and study of their physico-chemical properties
Grantee:Bruno de Almeida Piscelli
Support Opportunities: Scholarships in Brazil - Scientific Initiation