ORGN 377

The study of molecular receptors that can interact with biologically relevant substrates is a recurring theme in supramolecular chemistry.  Such investigations provide a better understanding of molecular recognition events and aid in the design of functional materials such as sensing and/or transport agents.  We have been studying the feasibility of constructing new crownophanes and aza-crownophanes (cyclophane derived crown ethers) that may display host-guest reactivity.  A range of functionalized cyclophanes has been prepared via a modular approach in which a benzannulation-macrocyclization reaction serves as the key transformation.  The ability of cyclophanes such as 1 to bind positively charged substrates has been examined in solution as well as the gas phase.  Structural features of various crownophanes in the solid-state (as determined by X-ray diffractometry) will also be discussed.