Mark G. Steinmetz, Ph.D.
Professor, Organic Chemistry
(414) 288-3535

Professor Steinmetz received his undergraduate education at the University of Kansas. After completing his Ph.D. in 1977 at the University of Wisconsin, his interests in photochemistry led him to a research fellowship at the Johns Hopkins University to study chemi- and bioluminescence. Professor Steinmetz joined the department in September 1979.

Research Fields
Our research develops new photochemically cleavable organic molecules. Photocleavable molecules have a wide range of practical applications. In cellular biology photocleavable compounds can be designed which rapidly release biomolecules when exposed to a flash of light. The released biomolecule can then trigger a biological process, which can be monitored on a microscopic level during time periods as short as nanoseconds or microseconds. Photocleavable linkers are used in peptide and protein synthesis, and photocleavable protecting groups are employed in DNA synthesis. In materials science applications photocleavable groups are used to manufacture microscopic patterns on surfaces. In such applications photocleavable groups are removed upon exposure to light or an acid is photochemically released which increases the solubility of the immediate surface surroundings. Most of our attention has focused upon compounds which release molecules rather than radicals. We are especially interested in cleavage via photogenerated zwitterionic intermediates which can cleave to ion pairs. In addition, we seek to use visible light to effect the photocleavage reactions. The field of graduate study is organic photochemistry. Students master organic synthesis and chromatographic separations of complex mixtures. They characterize unknown photochemical products using a NMR spectroscopy and additional spectroscopic techniques. Specialized knowledge is gained in the use of photochemical techniques, including time resolved techniques, to elucidate the mechanisms of photochemical reactions.

Selected Publications

"Time-Resolved pH-Jump Study of Photochemical Cleavage and Release of Carboxylic Acids from a-Keto Amides", Ma, C.; Steinmetz, M.G.*; Kopatz, E.J.; Rathore, R. Tetrahedron Lett. 2005, 46, 1045-1048.

“Photochemical Cleavage and Release of Carboxylic Acids from a-Keto Amides”, Ma, C.; Steinmetz, M.G.*; Kopatz, E.J.; Rathore, R. J. Org. Chem. 2005, 70, 4431-4442.

"Photochemical Cleavage and Release of Para-Substituted Phenols from a-Keto Amides", Ma, Chicheng; Chen, Yugang; Steinmetz, Mark G.* J. Org. Chem. 2006, 71, 4206-4215.

"Photoactivation of Amino-Substituted 1,4-Benzoquinones for Release of Carboxylate and Phenolate Leaving Groups Using Visible Light", Chen, Yugang; Steinmetz, Mark G.* J. Org. Chem. 2006, 71, 6053-6060.

Jia, J.; Sarker, M.; Steinmetz, M.G.*; Shukla, R.; Rathore, R. “Photochemical Elimination of Leaving Groups from Zwitterionic Intermediates Generated via Electrocyclic Ring Closure of a,b-Unsaturated Anilides”, J. Org. Chem. 2008, 73, 8867-8879.


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