Biradical with a polyfluorinated terphenylene backbone

Biradical with a polyfluorinated terphenylene backbone Full article

Journal

Russian Chemical Bulletin
ISSN: 1066-5285

Output data

Year: 2022, Volume: 71, Number: 8, Pages: 1670-1678 Pages count : 9 DOI: 10.1007/s11172-022-3577-0

Tags

organic paramagnets, organofl uorine compounds, stable organic biradicals, X-ray diff raction

Authors

Fedyushin P.A. ^1,2 , Serykh A.A. ^1,2 , Vinogradov A.S. ³ , Mezhenkova T.V. ³ , Platonov V.E. ³ , Nasyrova D.I. ^1,4 , Samigullina A.I. ¹ , Fedin M.V. ⁵ , Zayakin I.A. ¹ , Tretyakov E.V. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation
2	D. I. Mendeleev University of Chemical Technology of Russia, 9 pl. Miusskaya, 125047, Moscow, Russian Federation
3	N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk, Russian Federation
4	National Research University Higher School of Economics, 20 ul. Myasnitskaya, 101000, Moscow, Russian Federation
5	International Tomography Center, Siberian Branch of the Russian Academy of Sciences, Novosibirsk, Russian Federation

A method was developed for the synthesis of perfluoro-1,1′:4′,1″-terphenyl by the reaction of chloroperfluorobenzene with zinc dust followed by the reaction of the resulting mixture of C6F5ZnCl and (C6F5)2Zn with decafluorobiphenyl in the presence of KF. The reaction of perfluoro-1,1′:4′,1″-terphenyl with tert-butylamine in an autoclave gives the aminodefluorination product, 4,4″-bis(tert-butylamino)perfluoro-1,1′:4′,1″-terphenyl, and the oxidation of the latter with m-chloroperbenzoic acid affords a new stable nitroxide biradical 4,4″-bis(N-tert-butyl-N-oxylamino)perfluoro-1,1′:4′,1″-terphenyl in quantitative yield. The molecular and crystal structures of the diamine and the biradical were established by X-ray diffraction. According to the X-ray diffraction data, the planes of the paramagnetic moieties and the aromatic rings are significantly rotated with respect to each other, resulting in weak intramolecular exchange interactions between the paramagnetic centers.

Fedyushin P.A. , Serykh A.A. , Vinogradov A.S. , Mezhenkova T.V. , Platonov V.E. , Nasyrova D.I. , Samigullina A.I. , Fedin M.V. , Zayakin I.A. , Tretyakov E.V.
Biradical with a polyfluorinated terphenylene backbone
Russian Chemical Bulletin. 2022. V.71. N8. P.1670-1678. DOI: 10.1007/s11172-022-3577-0 WOS Scopus OpenAlex

Submitted:	Apr 12, 2022
Accepted:	May 25, 2022
Published print:	Sep 23, 2022

Web of science:	WOS:000859732900011
Scopus:	2-s2.0-85138726967
OpenAlex:	W4296832082

DB	Citing
Scopus	9
Web of science	9