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,N4′-di-tert-butyl-2,2′,3,3′,5,5′,6,6′-octafluorobiphenyl-4,4′-diamine with meta-chloroperoxybenzoic acid, led to the polyfluorinated nitroxide diradical, N,N′-(perfluorobiphenyl-4,4′-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° 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.
Highlights
Multi-spin organic molecules possess intriguing properties that are of basic research interest and have a significant potential for advanced technological applications [1,2,3,4,5,6,7]
We attempted to carry out a reaction of perfluorobiphenyl 1 with target multi-spin compounds
We attempted to carry out a reaction of perfluorobiphenyl 1 with terttert-butylamine, aiming to synthesize the corresponding diradical 3
Summary
Multi-spin organic molecules possess intriguing properties that are of basic research interest and have a significant potential for advanced technological applications [1,2,3,4,5,6,7]. These multi-spin molecules have recently emerged as promising building blocks for organic magnetic sensors [8], memory devices [9,10,11], spintronics [12], and spin filters [13,14], as well as for the probing of quantum interference effects in molecular conductance [15]. Realizing that the advances in the synthesis of nitroxide multi-spin molecules would
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