General purpose ditopic hydrogen bonding module and its use to generate unique polymer architectures

ORGN 609

Eric M. Todd, erictodd@scs.uiuc.edu, Department of Chemistry, University of Illinois, 600 South Mathews Ave., Urbana, IL 61801 and Steven C. Zimmerman, Department of Chemistry, University of Illinois at Urbana-Champaign, 600 S. Mathews Avenue, Urbana, IL 61801.
Hydrogen bonding provides a useful method for the self-assembly of complex architectures whose precise structure and overall stability is pre-programmed by the nature of the hydrogen bonding array and the orientation of the different arrays to each other. With the engineering of complex supramolecular structures in mind, hydroxyl functionalized bis(ureidodeazaptern), bis-DeAP-OH, has been designed and prepared on the gram scale. The orientation of the heterocycles and the entropic preference for discreet structures enables bis-DeAP-OH to assemble into robust cycle structures in nonpolar organic solvents. The hydroxyl group provides a synthetic handle to modify bis-DeAP-OH for any desired application and has been used to initiate the polymerization of cyclic esters and further functionalized to initiate the polymerization of styrene and methylmethacrylate. The resulting star polymers contain a completely self-assembled core and are capable of dynamic behavior in response to changes in the environment.

 

Molecular Recognition and Self-Assembly
1:00 PM-5:00 PM, Wednesday, March 28, 2007 McCormick Place Lakeside -- Room E352, Level 3, Oral

Division of Organic Chemistry

The 233rd ACS National Meeting, Chicago, IL, March 25-29, 2007