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. 2015 Aug 1;6(8):4712-4716.
doi: 10.1039/c5sc00724k. Epub 2015 Jun 5.

Profluorescent verdazyl radicals - synthesis and characterization

David Matuschek  1 , Steffen Eusterwiemann  1 , Linda Stegemann  2 , Carsten Doerenkamp  3 , Birgit Wibbeling  1 , Constantin G Daniliuc  1 , Nikos L Doltsinis  4 , Cristian A Strassert  2 , Hellmut Eckert  3   5 , Armido Studer  1
Affiliations

Profluorescent verdazyl radicals - synthesis and characterization

David Matuschek et al. Chem Sci. .

Abstract

The synthesis and characterization of various 6-oxo-verdazyl radicals and their diamagnetic styryl radical trapping products are presented. It is shown that styryl radical trapping products derived from N-phenyl verdazyls show fluorescence whereas the N-methyl congeners are non-fluorescent. In the parent N-phenyl verdazyls fluorescence is fully quenched which renders these compounds highly valuable profluorescent radical probes.

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Figures

Fig. 1
Fig. 1. Profluorescent verdazyls as radical probes.
Fig. 2
Fig. 2. X-ray structure of 10 (top) and 11 (bottom) (thermals ellipsoids are shown with 30% probability).
Fig. 3
Fig. 3. EPR spectrum of 1,3-bis(1,5-di-(4-octyloxy)phenyl-6-oxo-3-verdazyl)benzene (black)(14) and simulation (red).
Fig. 4
Fig. 4. Visualization and energies of the HOMOs and LUMOs of 16, 18, and 20 calculated with the PBE0 functional and the 6-31G* basis set at the optimized ground state geometry.
Fig. 5
Fig. 5. Normalized emission spectra in acetonitrile at room temperature ((a): 16–20; (b): 16–25) and at 77 K in a frozen glassy matrix of butyronitrile ((c): 16–24*; (d): 16–25).
Fig. 6
Fig. 6. N-Methyl tetrazin-3-ones 24, 24* and 25.
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