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. 2009 May 7;11(9):1871-4.
doi: 10.1021/ol9001575.

Synthesis of a BDPA-TEMPO biradical

Eric L Dane  1 , Thorsten Maly, Galia T Debelouchina, Robert G Griffin, Timothy M Swager
Affiliations

Synthesis of a BDPA-TEMPO biradical

Eric L Dane et al. Org Lett. .

Abstract

The synthesis and characterization of a biradical containing a 1,3-bisdiphenylene-2-phenylallyl (BDPA) free radical covalently attached to a 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) free radical are described. The synthesis of the biradical is a step toward improved polarizing agents for dynamic nuclear polarization (DNP).

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Figures

Figure 1
Figure 1
(a) X-ray ORTEP representation of 7 (50% probability level). (b) Rotamers of 7.
Figure 2
Figure 2
9 GHz liquid-state EPR of 9 (black) and 8 (red) in toluene. The regions with enlarged vertical scales (grey) show the forbidden singlet-triplet transitions. Experimental parameters: rt, microwave power 2 mW, sweep width 20 mT, modulation amplitude 10 mT.
Figure 3
Figure 3
140 GHz echo-detected solid-state EPR spectra of 9 (black), TEMPO (red), and BDPA (blue) in toluene. Experiments are performed at 20 K, with tp(π/2) = 44 ns, and typically 100 scans are averaged for each point.
Scheme 1
Scheme 1
BDPA radical syntheses
Scheme 2
Scheme 2
Synthesis of BDPA-TEMPO biradical.
See this image and copyright information in PMC

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References

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