Organic chemistry processes are used every day to synthesize medicines and materials. In the Douglas Group, our mission is to discover new methods that allow us to construct complex molecules. The laboratory is currently engaged in two broad fields of research:
1. Catalytic Methods in Functionalizing Single Bonds to Carbon
2. Organoelectronic Materials
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Catalytic Methods in Functionalizing Single Bonds to Carbon
The challenge of activating carbon-carbon sigma bonds (C-C bonds) inspires us to attempt activation in the presence of even more reactive functionality, including even the C-H bond. The key problem is not simply convincing a metal catalyst to insert into the bond, which we and others have already demonstrated. Rather, the problem is convincing the catalyst to conduct a useful molecular reorganization with high selectivity.
The C-C bonds adjacent to ketones can be activated in the presence of an acylquinoline. Intramolecular carboacylation of an alkene results in the construction of an all-carbon quaternary center.
 Dreis, A. M.; Douglas, C. J. J. Am. Chem. Soc. 2009, 131, 412-413.
Wentzel, M. T.; Reddy, V. J.; Hyster, T. K.; Douglas, C. J. Angew Chem. Int. Ed. 2009, 48, 6121-6123.
Low-cost, printed, organic electronic devices require new semiconducting materials. Rubrene, a tetracene, is widely recognized for its ability to conduct charge similar to silicon. In collaboration with University of Minnesota's Materials Research Science and Engineering Center (MRSEC), we are developing new methods for synthesizing tetracene derivatives. Our main goals are to ascertain correlations between molecular structure and material properties, and to discover new organoelectronic materials.
A. Stacks of tetrachlorotetracene along the b-axis with pitch stacking
angle of 71.53 degrees. B. Roll stacking angle of 82.67 degrees.
 Anthony, J. E. Angew. Chem. Int. Ed. 2008, 46, 452-483.
 a. Yagodkin, E.; Xia, Y.; Kalihari, V.; Frisbie, C. D.; Douglas, C. J. J. Phys. Chem. C. 2009, 13, 16544-16548. b. Yagodkin, E.; Douglas, C. J. Tetrahedron Lett. 2010, 51, 3037-3040.
Last updated 18 April 2011