Type of Publication: | Journal article |
Publication status: | Published |
Author: | Lampp, Lisa; Azarkh, Mykhailo; Drescher, Malte; Imming, Peter |
Year of publication: | 2019 |
Published in: | Tetrahedron ; 75 (2019), 18. - pp. 2737-2747. - ISSN 0040-4020. - eISSN 1464-5416 |
DOI (citable link): | https://dx.doi.org/10.1016/j.tet.2019.03.051 |
Summary: |
Two new derivatives of galvinoxyl (1), a perdeutered (2) and an adamantyl-analog (3) for potential applications as spin probes were synthesized. The synthesis with deuterated educts yielded 2 with 98% D. It exhibited an 18-line EPR spectrum in octanol with narrow peak-to-peak linewidth. The EPR spectrum of 3 was very similar to galvinoxyl, but with differences in the linewidth due to unresolved long-range couplings with adamantyl-protons. Compound 2 showed a higher response to oxygen (4.8 μT/% O2) than 1 (2.8 μT/% O2). The coupling pattern of 2 allowed the determination of oxygen at low levels (0–6%) by a new type of analysis of the EPR pattern. The stability of the radicals strongly depended on the amount of hydrogalvinoxyl, a by-product of the galvinoxyl synthesis, and the solvent type. A molecular mechanism for the stabilization by hydrogalvinoxyl and the influence of solvent type is proposed.
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Subject (DDC): | 540 Chemistry |
Keywords: | Galvinoxyl radicals, EPR, Oximetry, Mechanism of stabilization |
Bibliography of Konstanz: | Yes |
Refereed: | Yes |
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LAMPP, Lisa, Mykhailo AZARKH, Malte DRESCHER, Peter IMMING, 2019. Galvinoxyl radicals : Synthesis of new derivatives, determination of low oxygen contents, and stability studies. In: Tetrahedron. 75(18), pp. 2737-2747. ISSN 0040-4020. eISSN 1464-5416. Available under: doi: 10.1016/j.tet.2019.03.051
@article{Lampp2019-05Galvi-45933, title={Galvinoxyl radicals : Synthesis of new derivatives, determination of low oxygen contents, and stability studies}, year={2019}, doi={10.1016/j.tet.2019.03.051}, number={18}, volume={75}, issn={0040-4020}, journal={Tetrahedron}, pages={2737--2747}, author={Lampp, Lisa and Azarkh, Mykhailo and Drescher, Malte and Imming, Peter} }