Synthesis of Nitroxide Diradical Using a New Approach

Standard

Synthesis of Nitroxide Diradical Using a New Approach. / Fedyushin, Pavel; Rybalova, Tatyana; Asanbaeva, Nargiz et al.

In: Molecules (Basel, Switzerland), Vol. 25, No. 11, 2701, 11.06.2020.

Research output: Contribution to journal › Article › peer-review

Harvard

Fedyushin, P, Rybalova, T, Asanbaeva, N, Bagryanskaya, E, Dmitriev, A , Gritsan, N , Kazantsev, M & Tretyakov, E 2020, 'Synthesis of Nitroxide Diradical Using a New Approach', Molecules (Basel, Switzerland), vol. 25, no. 11, 2701. https://doi.org/10.3390/molecules25112701

APA

Fedyushin, P., Rybalova, T., Asanbaeva, N., Bagryanskaya, E., Dmitriev, A., Gritsan, N., Kazantsev, M., & Tretyakov, E. (2020). Synthesis of Nitroxide Diradical Using a New Approach. Molecules (Basel, Switzerland), 25(11), [2701]. https://doi.org/10.3390/molecules25112701

Vancouver

Fedyushin P, Rybalova T, Asanbaeva N, Bagryanskaya E, Dmitriev A , Gritsan N et al. Synthesis of Nitroxide Diradical Using a New Approach. Molecules (Basel, Switzerland). 2020 Jun 11;25(11):2701. doi: 10.3390/molecules25112701

Author

Fedyushin, Pavel ; Rybalova, Tatyana ; Asanbaeva, Nargiz et al. / Synthesis of Nitroxide Diradical Using a New Approach. In: Molecules (Basel, Switzerland). 2020 ; Vol. 25, No. 11.

BibTeX

@article{6d9be40cb5ec44e6a2bad1136a81cad7,

title = "Synthesis of Nitroxide Diradical Using a New Approach",

abstract = "A new synthetic pathway to diradical organic systems is proposed. The effectiveness of this approach was exemplified by the synthesis of a new nitroxide diradical. An interaction of perfluorobiphenyl with lithium tert-butylamide, followed by oxidation of the thusly formed N4,N40di-tert-butyl-2,20,3,30,5,50,6,60-octafluorobiphenyl-4,40-diamine with meta- chloroperoxybenzoic acid, led to the polyfluorinated nitroxide diradical, N,N0-(perfluorobiphenyl-4,40-diyl)bis(Ntert-butyl(oxyl)amine), with a good total yield. The polyfluorinated diradical is stable and can be isolated in free form and completely characterized. The structure of the nitroxide diradical was proved by single-crystal X-ray diffraction analysis. According to the X-ray diffraction data, the diradical is considerably twisted: dihedral angles between the planes of the nitroxide groups and aromatic cycles are 65.1◦ and 69.5◦, and between aromatic cycles 52.6◦. Quantum chemical calculations predict well-balanced size of both intramolecular and intermolecular exchange interactions with J from −2.65 to −1.14 cm−1",

keywords = "aromatic nucleophilic substitution, diradicals, fluoroarenes, nitroxides, tert-butylanilines, DESIGN, TRIPLET, NITRONYL NITROXIDE, COMPLEXES, RADICALS, MAGNETIC-PROPERTIES, GROUND-STATES, Models, Chemical, Nitrogen Oxides/chemical synthesis, Quantum Dots, X-Ray Diffraction, Halogenation, Molecular Structure",

author = "Pavel Fedyushin and Tatyana Rybalova and Nargiz Asanbaeva and Elena Bagryanskaya and Alexey Dmitriev and Nina Gritsan and Maxim Kazantsev and Evgeny Tretyakov",

year = "2020",

month = jun,

day = "11",

doi = "10.3390/molecules25112701",

language = "English",

volume = "25",

journal = "Molecules",

issn = "1420-3049",

publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",

number = "11",

}

RIS

TY - JOUR

T1 - Synthesis of Nitroxide Diradical Using a New Approach

AU - Fedyushin, Pavel

AU - Rybalova, Tatyana

AU - Asanbaeva, Nargiz

AU - Bagryanskaya, Elena

AU - Dmitriev, Alexey

AU - Gritsan, Nina

AU - Kazantsev, Maxim

AU - Tretyakov, Evgeny

PY - 2020/6/11

Y1 - 2020/6/11

N2 - A new synthetic pathway to diradical organic systems is proposed. The effectiveness of this approach was exemplified by the synthesis of a new nitroxide diradical. An interaction of perfluorobiphenyl with lithium tert-butylamide, followed by oxidation of the thusly formed N4,N40di-tert-butyl-2,20,3,30,5,50,6,60-octafluorobiphenyl-4,40-diamine with meta- chloroperoxybenzoic acid, led to the polyfluorinated nitroxide diradical, N,N0-(perfluorobiphenyl-4,40-diyl)bis(Ntert-butyl(oxyl)amine), with a good total yield. The polyfluorinated diradical is stable and can be isolated in free form and completely characterized. The structure of the nitroxide diradical was proved by single-crystal X-ray diffraction analysis. According to the X-ray diffraction data, the diradical is considerably twisted: dihedral angles between the planes of the nitroxide groups and aromatic cycles are 65.1◦ and 69.5◦, and between aromatic cycles 52.6◦. Quantum chemical calculations predict well-balanced size of both intramolecular and intermolecular exchange interactions with J from −2.65 to −1.14 cm−1

AB - A new synthetic pathway to diradical organic systems is proposed. The effectiveness of this approach was exemplified by the synthesis of a new nitroxide diradical. An interaction of perfluorobiphenyl with lithium tert-butylamide, followed by oxidation of the thusly formed N4,N40di-tert-butyl-2,20,3,30,5,50,6,60-octafluorobiphenyl-4,40-diamine with meta- chloroperoxybenzoic acid, led to the polyfluorinated nitroxide diradical, N,N0-(perfluorobiphenyl-4,40-diyl)bis(Ntert-butyl(oxyl)amine), with a good total yield. The polyfluorinated diradical is stable and can be isolated in free form and completely characterized. The structure of the nitroxide diradical was proved by single-crystal X-ray diffraction analysis. According to the X-ray diffraction data, the diradical is considerably twisted: dihedral angles between the planes of the nitroxide groups and aromatic cycles are 65.1◦ and 69.5◦, and between aromatic cycles 52.6◦. Quantum chemical calculations predict well-balanced size of both intramolecular and intermolecular exchange interactions with J from −2.65 to −1.14 cm−1

KW - aromatic nucleophilic substitution

KW - diradicals

KW - fluoroarenes

KW - nitroxides

KW - tert-butylanilines

KW - DESIGN

KW - TRIPLET

KW - NITRONYL NITROXIDE

KW - COMPLEXES

KW - RADICALS

KW - MAGNETIC-PROPERTIES

KW - GROUND-STATES

KW - Models, Chemical

KW - Nitrogen Oxides/chemical synthesis

KW - Quantum Dots

KW - X-Ray Diffraction

KW - Halogenation

KW - Molecular Structure

UR - http://www.scopus.com/inward/record.url?scp=85086623729&partnerID=8YFLogxK

U2 - 10.3390/molecules25112701

DO - 10.3390/molecules25112701

M3 - Article

C2 - 32545156

AN - SCOPUS:85086623729

VL - 25

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 11

M1 - 2701

ER -

ID: 24537804