Exploring new chemical reactions on self-assembled monolayers of alkanthiolates on gold by SAMDI-MS

ORGN 245

Jing Li, lij@uchicago.edu, Department of Chemistry and Howard Hughes Medical Institute, The University of Chicago, 929 East 57th Street, CIS E535, Chicago, IL 60637 and Milan Mrksich, mmrksich@midway.uchicago.edu, Department of Chemistry and Howard Hughes Medical Institute, University of Chicago, 929 East 57th Street, Chicago, IL 60637.
The ability to control the structures, and therefore the properties, of surfaces has made self-assembled monolayers a central element of studies in a broad range of interfacial problems. Yet, the development of interfacial reactions is still a difficult and slow process, owing to the challenges in characterizing the products and yields of the conversions. This presentation illustrates the use of matrix-assisted laser desorption/ionization and time-of-flight mass spectrometry (MALDI-TOF MS) to characterize the interfacial reaction products. This method was used to demonstrate sixteen high yielding organic transformations of functional groups presented on self-assembled monolayers. The method has been extended to screening reaction conditions to identify unexpected conversions of common functional groups. The combination of mass spectrometry methods to identify reaction products and self-assembled monolayers to control the reaction environments provides a new opportunity to both develop and discover interfacial reactions.
 

Combinatorial and Process Chemistry
8:00 AM-11:40 AM, Monday, March 26, 2007 McCormick Place East -- Room E350, Level 3, Oral

Division of Organic Chemistry

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