Structural investigations on quinone methides for understanding their properties in confined media.

Szarma, R.J.; Batsanov, A.S.; Kataky, R.; Baruah, J.B.

Abstract

Encapsulation of 4−[(4′-hydroxy−3′,5′-dimethylphenyl)(aryl)-methylene]−2,6−dimethyl-cyclohexa−2,5−dienones (when aryl=4−hydroxyphenyl 1, 4−methoxyphenyl 2, 2,3,4-trimethoxy phenyl 3) by β-cyclodextrin is studied. The compound 2 is selectively encapsulated by β-cyclodextrin. The result is rationalised by analysing the structural parameters from the crystal structure of 1–3. The visible spectra of the compounds 2 and 3 at pH 9.0 show red shifts on the absorption maxima upon addition of cetyltrimethylammonium bromide (CTAB). For example, addition of a solution of CTAB to aqueous ethanolic solution of 2 at pH 9 causes shift of the absorption at 578–593 nm (Δλmax=15 nm). The advantage of this observation is taken to use 2 and 3 to determine the critical micelle concentration of CTAB in basic medium.

Citation

Szarma, R., Batsanov, A., Kataky, R., & Baruah, J. (2006). Structural investigations on quinone methides for understanding their properties in confined media. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 55(1-2), 1-9. https://doi.org/10.1007/s10847-005-9001-1

• Journal Article Type: Article
• Publication Date: 2006
• Journal: Journal of Inclusion Phenomena and Macrocyclic Chemistry
• Print ISSN: 0923-0750
• Electronic ISSN: 1573-1111
• Publisher: Springer
• Peer Reviewed: Peer Reviewed
• Volume: 55
• Issue: 1-2
• Pages: 1-9
• DOI: https://doi.org/10.1007/s10847-005-9001-1
• Keywords: Critical micelle concentration, Crystal structures, Cyclodextrin, Encapsulation, Quinone-methides.