Synthesis, characterization, and application of highly stable carbon-centered radicals

ORGN 358

Eric L. Dane, edane@mit.edu1, Timothy M. Swager, tswager@MIT.EDU1, and Robert G. Griffin, rgg@mit.edu2. (1) Institute of Soldier Nanotechnologies, Massachusetts Insitute of Technology, 77 Mass. Avenue, Cambridge, MA 02139, (2) Francis Bitter Magnet Laboratory, Dept. of Chemistry, Massachusetts Institute of Technology, 170 Albany Street, Cambridge, MA 02139

 

 

 

In 1931, C.F. Koelsch prepared a remarkably stable hydrocarbon free radical called BDPA.  We initially became interested in this molecule as a component of a biradical to enhance the sensitivity of carbon-13 solid-state NMR samples using dynamic nuclear polarization, and have prepared a biradical containing a BDPA unit tethered to a TEMPO unit.  In order to synthesize the biradical, the mechanism of the key transformation leading to the formation of BDPA's carbon skeleton was investigated. Inspired by BDPA's structure and properties, we are working to prepare conducting polymers that incorporate BDPA to explore whether these materials will display unique electrical, photophysical, and magnetic properties, as well as investigating the BDPA-TEMPO biradical's effectiveness in dynamic nuclear polarization.