Toward the synthesis of new CTV derivatives

ORGN 787

Andria Panagopoulos, apanago@luc.edu, Department of Chemistry, Loyola University Chicago, 1068 West Sheridan Road, Flanner Hall, Chicago, IL 60626 and Daniel P. Becker, dbecke3@luc.edu, Department of Chemistry, Loyola University, 6525 North Sheridan Road, Chicago, IL 60626.
Supramolecular chemistry involves the formation of complex molecular entities that have the capacity to participate in specific molecular recognition of guest molecules. A commonly employed scaffold in supramolecular chemistry is the trimeric crown-shaped molecule cyclotriveratrylene (CTV). CTV has been studied extensively for its capability of binding a number of smaller organic and organometallic guests within its bowl-shaped cleft and has been used as a building block enabling the construction of more complex cryptophanes. The goal of this research is the synthesis and characterization of a novel cyclophane, tribenzo-1,4,7-triazacyclononene and derivatives thereof. These new cyclophanes should have greater versatility than the parent hydrocarbon macrocycle including greatly enhanced water solubility, ability to coordinate to metal ligands, the potential for use in drug delivery, and unique optical and liquid crystal properties. Progress towards these molecules have employed both Buchwald-Hartwig palladium catalyzed N-arylation as well as benzyne chemistry. Both sets of conditions for the final closure step have led to an unexpected methyl transfer followed by closure to the phenazine derivative. Progress toward tribenzo-1,4,7-triazacyclononene and its derivatives will be presented.