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

Autor(es):Mostrar menos -

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]

Afiliação do(s) autor(es)

^[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

• Tipo de documento: Artigo Científico
• Fonte: CHEMICAL SCIENCE; v. 12, n. 28, p. 9712-9719, JUL 28 2021.
• Citações Web of Science: 1

Resumo

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)

• Processo FAPESP: 18/03910-1 - Estudos físico-químicos de compostos orgânicos fluorados: abordagens experimental e teórica
• Beneficiário: Rodrigo Antonio Cormanich
• Modalidade de apoio: Auxílio à Pesquisa - Jovens Pesquisadores
• Processo FAPESP: 19/03855-3 - Síntese de derivados fluorados do timol e do carvacrol e estudo de suas propriedades físico-químicas
• Beneficiário: Bruno de Almeida Piscelli
• Modalidade de apoio: Bolsas no Brasil - Iniciação Científica