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45440-B1
Exploiting the Oxacalixarene Scaffold: Structural Diversity, Macrobicyclic Hosts, Multicalixarenes, and Molecular Tweezers

Jeffrey L. Katz, Colby College

Research Summary September 2006 Ð September 2007

My research group continues to develop simple methods for the synthesis of oxacalixarenes and related structures, building upon our successful single-step approach to oxacalix[4]arenes 8 based on nucleophilic aromatic substitution reactions of meta-diphenols 1 with 1,5-difluoro-2,4-dinitrobenzene (2).  We have expanded this method to include azaheterocyclic electrophiles 2-7 for the formation of oxacalix[4]arenes with embedded pyridines, pyrazines, and pyrimidines.

We have also synthesized oxacalixarenes incorporating dichloronaphthyridine 10 (below).  These naphthyridine-embedded oxacalixarenes (such as 13 and 14) have expanded concave surfaces relative to the macrocycles shown above.  We have shown that oxacalixarenes 10 function as "molecular tweezers" -- binding certain aromatic guest molecules on the interior surface.  NMR spectroscopy, fluorometery, and isothermal titration calorimetery are being used to study the molecular recognition properties of our oxacalixarenes.

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