Separation of dimethylcyclohexane stereoisomers by selective guest inclusion of host compound of guanidinium o-terphenyl-4,4′-disulfonate

Jinsoo Kim, Jongheop Yi, Michael Ward, Woo Sik Kim

Research output: Contribution to journalArticle

Abstract

Using the molecular recognizability of guanidinium o-terphenyl-4,4′-disulfonate (G2o-TPDS) host compound to guests, the stereoisomers of dimethylcyclohexane (DMCH) were separated. In a binary competition of cis- and trans-isomers of 1,2-, 1,3- and 1,4-DMCH, it was found that the equatorial, equatorial (e,e) conformers (trans-1,2-, cis-1,3- and trans-1,4-DMCH) were predominantly selected as guests to the host inclusion against the axial, equatorial (a,e) conformers (cis-1,2-, trans-1,3- and cis-1,4-DMCH) due to the spatial configuration of the nano-cavity in the host frame. Furthermore, among the three e,e-conformers, trans-1,2- and trans-1,4-DMCH were preferentially accommodated to the host frame rather than cis-1,3-DMCH. However, there was little guest selectivity of the host frame between trans-1,2- and trans-1,4-DMCH. From powder X-ray diffraction and differential scanning calorimetry of the host-guest inclusion compounds, it was revealed that trans-1,2- and trans-1,4-DMCH were guest templates for stronger G2o-TPDS host-frame structure than other isomers, resulting in the more stable host-guest inclusion compounds of G2o-TPDS (trans-1,2-DMCH) and G2o-TPDS (trans-1,4-DMCH). So, they required higher energy and onset temperature to release guest molecules from the host frames than other inclusion compounds. This thermal analysis of the host-guest inclusion compounds was consistent with the guest selectivity of the host frame in the binary mixture, implying the potential method to predict the selective guest in the inclusion compound in the guest mixture.

Original languageEnglish (US)
Pages (from-to)57-64
Number of pages8
JournalSeparation and Purification Technology
Volume66
Issue number1
DOIs
StatePublished - Apr 7 2009

Fingerprint

Stereoisomerism
Guanidine
Isomers
Binary mixtures
X ray powder diffraction
Thermoanalysis
Differential scanning calorimetry
Molecules

Keywords

  • Inclusion compound
  • Selective separation
  • Stereoisomers
  • Thermal stability

ASJC Scopus subject areas

  • Analytical Chemistry
  • Filtration and Separation

Cite this

Separation of dimethylcyclohexane stereoisomers by selective guest inclusion of host compound of guanidinium o-terphenyl-4,4′-disulfonate. / Kim, Jinsoo; Yi, Jongheop; Ward, Michael; Kim, Woo Sik.

In: Separation and Purification Technology, Vol. 66, No. 1, 07.04.2009, p. 57-64.

Research output: Contribution to journalArticle

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abstract = "Using the molecular recognizability of guanidinium o-terphenyl-4,4′-disulfonate (G2o-TPDS) host compound to guests, the stereoisomers of dimethylcyclohexane (DMCH) were separated. In a binary competition of cis- and trans-isomers of 1,2-, 1,3- and 1,4-DMCH, it was found that the equatorial, equatorial (e,e) conformers (trans-1,2-, cis-1,3- and trans-1,4-DMCH) were predominantly selected as guests to the host inclusion against the axial, equatorial (a,e) conformers (cis-1,2-, trans-1,3- and cis-1,4-DMCH) due to the spatial configuration of the nano-cavity in the host frame. Furthermore, among the three e,e-conformers, trans-1,2- and trans-1,4-DMCH were preferentially accommodated to the host frame rather than cis-1,3-DMCH. However, there was little guest selectivity of the host frame between trans-1,2- and trans-1,4-DMCH. From powder X-ray diffraction and differential scanning calorimetry of the host-guest inclusion compounds, it was revealed that trans-1,2- and trans-1,4-DMCH were guest templates for stronger G2o-TPDS host-frame structure than other isomers, resulting in the more stable host-guest inclusion compounds of G2o-TPDS (trans-1,2-DMCH) and G2o-TPDS (trans-1,4-DMCH). So, they required higher energy and onset temperature to release guest molecules from the host frames than other inclusion compounds. This thermal analysis of the host-guest inclusion compounds was consistent with the guest selectivity of the host frame in the binary mixture, implying the potential method to predict the selective guest in the inclusion compound in the guest mixture.",
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AB - Using the molecular recognizability of guanidinium o-terphenyl-4,4′-disulfonate (G2o-TPDS) host compound to guests, the stereoisomers of dimethylcyclohexane (DMCH) were separated. In a binary competition of cis- and trans-isomers of 1,2-, 1,3- and 1,4-DMCH, it was found that the equatorial, equatorial (e,e) conformers (trans-1,2-, cis-1,3- and trans-1,4-DMCH) were predominantly selected as guests to the host inclusion against the axial, equatorial (a,e) conformers (cis-1,2-, trans-1,3- and cis-1,4-DMCH) due to the spatial configuration of the nano-cavity in the host frame. Furthermore, among the three e,e-conformers, trans-1,2- and trans-1,4-DMCH were preferentially accommodated to the host frame rather than cis-1,3-DMCH. However, there was little guest selectivity of the host frame between trans-1,2- and trans-1,4-DMCH. From powder X-ray diffraction and differential scanning calorimetry of the host-guest inclusion compounds, it was revealed that trans-1,2- and trans-1,4-DMCH were guest templates for stronger G2o-TPDS host-frame structure than other isomers, resulting in the more stable host-guest inclusion compounds of G2o-TPDS (trans-1,2-DMCH) and G2o-TPDS (trans-1,4-DMCH). So, they required higher energy and onset temperature to release guest molecules from the host frames than other inclusion compounds. This thermal analysis of the host-guest inclusion compounds was consistent with the guest selectivity of the host frame in the binary mixture, implying the potential method to predict the selective guest in the inclusion compound in the guest mixture.

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