BDPA is an unusually stable radical compound due to the extent to which its electrons are delocalized through resonance structures.
[4] BDPA and closely related compounds are used as molecular standards in electron paramagnetic resonance (EPR) and electron nuclear double resonance (ENDOR) experiments,[5][6] and as a polarizing agent in dynamic nuclear polarization (DNP) nuclear magnetic resonance (NMR) experiments.
[9] The compound was first synthesized by C. Frederick Koelsch while he was a postdoctoral fellow at Harvard University in the 1930s.
Subsequent experimental evidence and quantum mechanics calculations suggested his interpretation of the original experiment was correct, resulting in the publication of the paper in 1957, nearly 25 years after the original experiments.
[1][10][11] Although the original report described stability on the order of years, modern experiments suggest that this family of compounds, while unusually stable for radicals, shows measurable degradation in months after preparation.