High-affinity quadruply hydrogen-bonding module mediated self-assembly on surfaces

ORGN 610

Darrell W. Kuykendall, dkuyken2@uiuc.edu, Hugo C. Ong, hugoong@uiuc.edu, and Steven C. Zimmerman, sczimmer@uiuc.edu. Department of Chemistry, Roger Adams Laboratory, University of Illinois at Urbana-Champaign, 600 South Mathews Avenue, Urbana, IL 61801
A urea of 7-deazaguanine (DeUG, 1), a high-affinity quadruply hydrogen-bonding module complement to 2,7-diamido-1,8-naphthyridine (DAN, 2), has been synthesized bearing functionality that facilitates covalent incorporation into a wide range of materials via the Huisgen 1,3-dipolar cycloaddition (“click”) reaction. DeUG was designed as a robust analogue of our recently reported urea of guanosine (UG). The design, synthesis and complexation behavior of DeUG will be presented. Additionally, DeUG has been attached to a variety of silica surfaces using the click methodology. The self-assembly of DAN analogues on these surfaces will also be presented.

 

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