Toward the synthesis of new CTV derivatives

ORGN 387

Andria Panagopoulos, apanago@luc.edu and Daniel Becker, dbecke3@luc.edu. Department of Chemistry, Loyola University Chicago, 1068 West Sheridan Road, Flanner Hall, 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. Cyclophanes are comprised of aromatic units with bridging chains that may form cage-like structures and have applications in molecular and receptor recognition, and they are also used as building blocks for organic catalysts. 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. The new cyclophane should have greater versatility than the parent hydrocarbon macrocycle including greatly enhanced water solubility, the potential for use in drug delivery, and unique optical and liquid crystal properties. Progress toward the synthesis of tribenzo-1,4,7-triazacyclononene will be discussed.