Tailoring Magnetic Features in Zigzag-Edged Nanographenes by Controlled Diels-Alder Reactions.

Autor: Ajayakumar MR; Center for Advancing Electronics Dresden (cfaed) &, Faculty of Chemistry and Food Chemistry, Technische Universität Dresden, Mommsenstrasse 4, 01062, Dresden, Germany., Fu Y; Center for Advancing Electronics Dresden (cfaed) &, Faculty of Chemistry and Food Chemistry, Technische Universität Dresden, Mommsenstrasse 4, 01062, Dresden, Germany., Liu F; Leibniz Institute for Solid State and Materials Research, Helmholtzstraße 20, 01069, Dresden, Germany., Komber H; Leibniz-Institut für Polymerforschung Dresden e. V., Hohe Straße 6, 01069, Dresden, Germany., Tkachova V; Center for Advancing Electronics Dresden (cfaed) &, Faculty of Chemistry and Food Chemistry, Technische Universität Dresden, Mommsenstrasse 4, 01062, Dresden, Germany., Xu C; Helmholtz-Zentrum Dresden-Rossendorf, Institute of Ion Beam Physics and Materials Research, Bautzner Landstrasse 400, Dresden, 01328, Germany., Zhou S; Helmholtz-Zentrum Dresden-Rossendorf, Institute of Ion Beam Physics and Materials Research, Bautzner Landstrasse 400, Dresden, 01328, Germany., Popov AA; Leibniz Institute for Solid State and Materials Research, Helmholtzstraße 20, 01069, Dresden, Germany., Liu J; Department of Chemistry and State Key Laboratory of Synthetic Chemistry, The University of Hong Kong, Pokfulam Road, 999077, Hong Kong, P. R. China., Feng X; Center for Advancing Electronics Dresden (cfaed) &, Faculty of Chemistry and Food Chemistry, Technische Universität Dresden, Mommsenstrasse 4, 01062, Dresden, Germany.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2020 Jun 10; Vol. 26 (33), pp. 7497-7503. Date of Electronic Publication: 2020 May 12.
DOI: 10.1002/chem.202001130
Abstrakt: Nanographenes (NGs) with tunable electronic and magnetic properties have attracted enormous attention in the realm of carbon-based nanoelectronics. In particular, NGs with biradical character at the ground state are promising building units for molecular spintronics. However, most of the biradicaloids are susceptible to oxidation under ambient conditions and photolytic degradation, which hamper their further applications. Herein, we demonstrated the feasibility of tuning the magnetic properties of zigzag-edged NGs in order to enhance their stability via the controlled Diels-Alder reactions of peri-tetracene (4-PA). The unstable 4-PA (y 0 =0.72; half-life, t 1/2 =3 h) was transformed into the unprecedented benzo-peri-tetracenes (BPTs) by a one-side Diels-Alder reaction, which featured a biradical character at the ground state (y 0 =0.60) and exhibited remarkable stability under ambient conditions for several months. In addition, the fully zigzag-edged circumanthracenes (CAs) were achieved by two-fold or stepwise Diels-Alder reactions of 4-PA, in which the magnetic properties could be controlled by employing the corresponding dienophiles. Our work reported herein opens avenues for the synthesis of novel zigzag-edged NGs with tailor-made magnetic properties.
(© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)
Databáze: MEDLINE
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