{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,17]],"date-time":"2026-10-17T21:33:35Z","timestamp":1792272815414,"version":"4.4.0"},"reference-count":39,"publisher":"MDPI AG","issue":"11","license":[{"start":{"date-parts":[[2020,6,11]],"date-time":"2020-06-11T00:00:00Z","timestamp":1591833600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100012190","name":"Ministry of Science and Higher Education of the Russian Federation","doi-asserted-by":"publisher","award":["RFMEFI61619X0116"],"award-info":[{"award-number":["RFMEFI61619X0116"]}],"id":[{"id":"10.13039\/501100012190","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>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,N4\u2032-di-tert-butyl-2,2\u2032,3,3\u2032,5,5\u2032,6,6\u2032-octafluorobiphenyl-4,4\u2032-diamine with meta-chloroperoxybenzoic acid, led to the polyfluorinated nitroxide diradical, N,N\u2032-(perfluorobiphenyl-4,4\u2032-diyl)bis(N-tert-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\u00b0 and 69.5\u00b0, and between aromatic cycles 52.6\u00b0. Quantum chemical calculations predict well-balanced size of both intramolecular and intermolecular exchange interactions with J from \u22122.65 to \u22121.14 cm\u22121.<\/jats:p>","DOI":"10.3390\/molecules25112701","type":"journal-article","created":{"date-parts":[[2020,6,16]],"date-time":"2020-06-16T00:50:49Z","timestamp":1592268649000},"page":"2701","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":15,"title":["Synthesis of Nitroxide Diradical Using a New Approach"],"prefix":"10.3390","volume":"25","author":[{"given":"Pavel","family":"Fedyushin","sequence":"first","affiliation":[{"name":"N. N. Vorozhtsov Institute of Organic Chemistry, 9 Ac. Lavrentieva Avenue, 630090 Novosibirsk, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2398-5271","authenticated-orcid":false,"given":"Tatyana","family":"Rybalova","sequence":"additional","affiliation":[{"name":"N. N. Vorozhtsov Institute of Organic Chemistry, 9 Ac. Lavrentieva Avenue, 630090 Novosibirsk, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nargiz","family":"Asanbaeva","sequence":"additional","affiliation":[{"name":"N. N. Vorozhtsov Institute of Organic Chemistry, 9 Ac. Lavrentieva Avenue, 630090 Novosibirsk, Russia"},{"name":"Department of Physics, Novosibirsk State University, 2 Pirogova Str., 630090 Novosibirsk, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0057-383X","authenticated-orcid":false,"given":"Elena","family":"Bagryanskaya","sequence":"additional","affiliation":[{"name":"N. N. Vorozhtsov Institute of Organic Chemistry, 9 Ac. Lavrentieva Avenue, 630090 Novosibirsk, Russia"},{"name":"Department of Physics, Novosibirsk State University, 2 Pirogova Str., 630090 Novosibirsk, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alexey","family":"Dmitriev","sequence":"additional","affiliation":[{"name":"Department of Physics, Novosibirsk State University, 2 Pirogova Str., 630090 Novosibirsk, Russia"},{"name":"V. V. Voevodski Institute of Chemical Kinetics and Combustion, 3 Institutskaya Str., 630090 Novosibirsk, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2263-1300","authenticated-orcid":false,"given":"Nina","family":"Gritsan","sequence":"additional","affiliation":[{"name":"Department of Physics, Novosibirsk State University, 2 Pirogova Str., 630090 Novosibirsk, Russia"},{"name":"V. V. Voevodski Institute of Chemical Kinetics and Combustion, 3 Institutskaya Str., 630090 Novosibirsk, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2869-1777","authenticated-orcid":false,"given":"Maxim","family":"Kazantsev","sequence":"additional","affiliation":[{"name":"N. N. Vorozhtsov Institute of Organic Chemistry, 9 Ac. Lavrentieva Avenue, 630090 Novosibirsk, Russia"},{"name":"Department of Natural Sciences, Novosibirsk State University, 2 Pirogova Str., 630090 Novosibirsk, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1540-7033","authenticated-orcid":false,"given":"Evgeny","family":"Tretyakov","sequence":"additional","affiliation":[{"name":"N. N. Vorozhtsov Institute of Organic Chemistry, 9 Ac. Lavrentieva Avenue, 630090 Novosibirsk, Russia"},{"name":"Department of Natural Sciences, Novosibirsk State University, 2 Pirogova Str., 630090 Novosibirsk, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2020,6,11]]},"reference":[{"key":"ref_1","unstructured":"Miller, J.S. (2018). High Spin Organic Molecules, in: World Scientific Reference on Spin in Organics, World Scientific Publishing Co. Pte. Ltd."},{"key":"ref_2","doi-asserted-by":"crossref","unstructured":"Nishinaga, T. (2016). Organic Redox Systems. 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