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Galvinoxyl radicals : Synthesis of new derivatives, determination of low oxygen contents, and stability studies

Galvinoxyl radicals : Synthesis of new derivatives, determination of low oxygen contents, and stability studies

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.
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} }

2019-05-29T06:58:23Z 2019-05 2019-05-29T06:58:23Z Azarkh, Mykhailo Imming, Peter Drescher, Malte 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/% O<sub>2</sub>) than 1 (2.8 μT/% O<sub>2</sub>). 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. Drescher, Malte Lampp, Lisa eng Imming, Peter Galvinoxyl radicals : Synthesis of new derivatives, determination of low oxygen contents, and stability studies Azarkh, Mykhailo Lampp, Lisa

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