The Troger's base framework is a rigid V-shaped chiral unit that is an attractive building block for the construction of more complex architectures. However, its susceptibility to acid-catalyzed racemization has limited many of its potential applications. The use of ethano-strapped analogues (where a CH2CH2 group replaces the CH2 strap between the two nitrogen atoms of the bridge) removes this limitation, and the compounds are configurationally stable in acidic media. The ethano-strapped analogues retain the attractive V-shape and the aromatic "walls" of the cavity are approximately 10° closer to one another in comparison with their methano-strapped analogues. A range of ethano-strapped analogues are now available in enantiomerically pure form, on a multigram scale. The use of some of these compounds in the preparation of new materials will be described.

Structured materials from a supramolecular approach

251st National Meeting (2016)

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