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dc.contributor.authorBaker, M.
dc.contributor.authorBrown, David
dc.contributor.authorHeath, C.
dc.contributor.authorSkelton, B.
dc.contributor.authorWhite, A.
dc.contributor.authorWilliams, C.
dc.identifier.citationBaker, Murray and Brown, David H. and Heath, Charles and Skelton, Brian and White, Allan and Williams, Charlotte. 2008. Azolium-Linked Cyclophanes: Effects of Structure, Solvent, and Counteranions on Solution Conformation Behavior. Journal of Organic Chemistry 73 (23): pp. 9340-9352.

This paper describes the synthesis, structural characterization, and solution behavior of some xylyllinked imidazolium and benzimidazolium cyclophanes decorated with alkyl or alkoxy groups. The addition of alkyl/alkoxy chains to the cyclophanes allows for studies in chlorinated solvents, whereas previous solution studies of azolium cyclophanes have generally required highly polar solvents. The azolium cyclophanes may exist in a syn/syn conformation (azolium rings mutually syn, arene rings mutually syn) or a syn/anti conformation (azolium rings mutually syn, arene rings mutually anti). The preferred conformation is significantly affected by (i) binding of bromide (ion pairing) to the protons on theimidazolium or benzimidazolium rings, which occurs in solutions of bromide salts of the cyclophanes inchlorinated solvents, and (ii) the addition of alkoxy groups to the benzimidazolium cyclophanes. Thesestructural modifications have also led to cyclophanes that adopt conformations not previously identifiedfor similar azolium cyclophane analogues.Detailed 1H NMR studies for one cyclophane identified binding of bromide at two independent sites within the cyclophane.

dc.publisherAmerican Chemical Society
dc.titleAzolium-Linked Cyclophanes: Effects of Structure, Solvent, and Counteranions on Solution Conformation Behavior
dc.typeJournal Article
dcterms.source.titleJournal of Organic Chemistry

Open access to this article will be available 12 months after publication via the website of the American Chemical Society.

curtin.departmentNanochemistry Research Institute (Research Institute)
curtin.accessStatusOpen access
curtin.facultyICT & Emerging Technology
curtin.facultyNanochemistry Research Institute (NRI)

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