Quantum-Chemical Simulation of the Structure of Charge-Transfer Complexes of 9,10-Phenanthrenequinone Nitro-Derivatives
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tum-Chemical Simulation of the Structure of Charge-Transfer Complexes of 9,10-Phenanthrenequinone Nitro-Derivatives with Phenanthrene. Crystal and Molecular Structure of 1 : 1 Complex of 2,4,7-Trinitro-9,10-phenanthrenequinone with Phenanthrene R. V. Linkoa,*, M. A. Ryabova, P. V. Strashnova, N. A. Polyanskayaa, V. V. Davydova, P. V. Dorovatovskiib, and V. N. Khrustaleva,c a Peoples’ Friendship
University of Russia (RUDN University), Moscow, 117198 Russia National Research Center “Kurchatov Institute,” Moscow, 123182 Russia c N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Moscow, 119991 Russia *e-mail: [email protected] b
Received May 14, 2020; revised May 14, 2020; accepted May 22, 2020
Abstract—Data on the structure and properties of charge transfer complexes of nitro derivatives of 9,10-phenanthrenequinone (acceptor) with phenanthrene (donor) were obtained by quantum chemical calculations. The energies of complex formation, the average distances between donor and acceptor planes, and the total charge transfer amounts were calculated. 1,3,6-Trinitro-9,10-phenanthrenequinone was shown to be the strongest acceptor in the studied series. The crystal and molecular structure of the 1 : 1 complex of 2,4,7-trinitro-9,10-phenanthrenequinone with phenanthrene [C14H5N3O8·C14H10] was determined by X-ray structural analysis. Keywords: 9,10-phenanthrenequinone nitro-derivatives, phenanthrene, charge-transfer complexes, quantum chemical simulation, X-ray structural analysis
DOI: 10.1134/S1070363220100096 Charge transfer complexes (CTC) have a wide range of unique physical properties. They demonstrate the properties of an insulator [1] and a metal [2, 3], superconductivity [4, 5] and photoconductivity [6], ferromagnetism [3, 7], antiferromagnetism [8, 9], and ferroelectricity [10, 11], as well as other properties [12]. The main factor that determines the properties of CTC is the nature of the donor (D) and acceptor (A) of π-electrons, and, in particular, the energy difference between the lowest unoccupied molecular orbital (LUMO) of an acceptor and the highest occupied molecular orbital (HOMO) of a donor [13, 14]. In addition, the properties of CTC are affected by the stoichiometric composition of complexes [15] and their polymorphic modification [16, 17]. The search for new effective acceptors, obtaining CTC with various donors on the basis of these acceptors, and studying their properties are still relevant and promising.
A fairly wide range of π-electron acceptors containing various numbers of nitro groups was formed on the basis of 9,10-phenanthrenquinone, but only one work is devoted to the study of CTC based on them [18]. The aim of this study was to obtain and study the structure and properties of CTC of 9,10-phenanthrenquinone nitro derivatives with phenanthrene (Phen). To achieve this aim, such acceptors as 9,10-phenanthrenquinone 1 and its derivatives 2–10 containing from one to three nitro groups, and also a bromine atom, were studied (Scheme 1). In the formation of CTC involving n
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