European Journal of Inorganic Chemistry p. 517 - 524 (2018)
Update date:2022-08-11
Topics:
Kumar, Varun
Shova, Sergiu
Maurel, Vincent
Novitchi, Ghenadie
Train, Cyrille
The synthesis and crystallization of two verdazyl radicals, 1,5-dimethyl-3-(4′-carboxyphenyl)-6-oxoverdazyl HIMe and 1,5-diisopropyl-3-(4′-carboxyphenyl)-6-oxoverdazyl HIiPr, are described. The electrochemical studies reveal that the oxidation of the two radicals is reversible, whereas their reduction is irreversible. The EPR spectrum of both radicals essentially exhibits a nine-line pattern related to the mean hyperfine interaction of the unpaired electron with the nitrogen atoms of the verdazyl cycle. The single-crystal X-ray diffraction of the intermediates towards HIiPr allows a fine description of the cyanoborane adduct, which is the key intermediate of this synthesis. The verdazyl radicals themselves are obtained as single crystals. In the case of HIiPr, depending on the solvent, two polymorphs are crystallized. The structure resolution reveals that, in the solid state, the organization of the verdazyl radicals is governed by both H-bonding and π–π interactions and is reminiscent of the H-bonded structures that can be present in solution. Within the 1D π stacks observed in the three compounds, the verdazyl–verdazyl distance varies from 4.88 ? in HIMe to 7.90 ? in HaIiPr. This modulation of the distance strongly influences the antiferromagnetic intermolecular exchange interaction between π-stacked radicals, which goes from J = –90 cm–1 (H = –JΣSiSi+1) for HIMe to –12.96(3) cm–1 for HbIiPr and –0.92 cm–1 for HaIiPr.
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