Selenacalix[3]triazines: Anion Versus Proton Association

Selenacalix[3]triazines, cyclotrimeric metacyclophanes with direct Se linkages between the heteroaryl constituents, were shown to associate with various guest species. The preorganization of three electron deficient triazine rings allows for anions to bind through anion‐π interactions, and alignment...

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Bibliographic Details
Published in:European journal of organic chemistry 2013-04, Vol.2013 (11), p.2085-2090
Main Authors: Van Rossom, Wim, Thomas, Joice, Terentyeva, Tatyana G., Maes, Wouter, Dehaen, Wim
Format: Article
Language:English
Subjects:
Anions
Calixarenes
Host-guest systems
Protonation
Protons
Selenium
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Summary:Selenacalix[3]triazines, cyclotrimeric metacyclophanes with direct Se linkages between the heteroaryl constituents, were shown to associate with various guest species. The preorganization of three electron deficient triazine rings allows for anions to bind through anion‐π interactions, and alignment of the central nitrogen lone pairs and the well‐defined size of the macroring enable association with a single proton. Extended UV/Vis titration studies indicated a clear difference in complexation behavior depending on the outer‐rim substitution pattern. The host–guest properties of analogous selena‐ and thiacalix[3]triazines were found to be notably different. Selenacalix[3]triazines were shown to interact with various anionic guests, and their complexation behavior (protonation versus pure anion binding) was dependent on the outer‐rim substitution pattern. Relative to the analogous thiacalix[3]triazine, the host–guest properties are notably different.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201201548