Abstract
The new compound 1,2-bis[(2,6-diisopropyl-4-iodophenyl)imino]acenaphthene (I2-dppbian, 1) was synthesized by the condensation of acenaphthenequinone with 2,6-diisopropyl-4-iodoaniline. The reaction of 1 with zinc chloride aff orded the complex [(I2-dpp-bian)ZnCl2] (2) with the neutral diimine ligand. The reaction of 1 with diethyl malonate (DEM) in the presence of copper(I) iodide and cesium carbonate gave 1,2-bis[(2,6-diisopropyl-4-diethylmalonophenyl) imino]acenaphthene (DEM2-dpp-bian, 3). The diamagnetic copper complex [(DEM2-dpp-bian)CuCl] (4) was prepared by the reaction of compound 3 with CuCl. Compounds 1–4 were characterized by elemental analysis, NMR spectroscopy, and IR spectroscopy. The molecular structures of complexes 2 and 4 were determined by single-crystal X-ray diff raction.
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Y. M. Litvinova, Y. M. Gayfulin, K. A. Kovalenko, D. G. Samsonenko, J. Leusen, I. V. Korolkov, V. P. Fedin, Y. V. Mironov, Inorg. Chem., 2018, 57, 2072.
D. M. D’Alessandro, Chem. Commun., 2016, 52, 8957.
C. Pettinari, F. Marchetti, N. Mosca, G. Tosia, A. Drozdov, Polym. Int., 2017, 66, 731.
S. Kitagawa, S. Kawata, Coord. Chem. Rev., 2002, 224, 11.
Z. Zhang, H. Yoshikawa, K. Awaga, J. Am. Chem. Soc., 2014, 136, 16112.
T. C. Narayan, T. Miyakai, S. Seki, M. Dinca, J. Am. Chem. Soc., 2012, 134, 12932.
S. S. Park, E. R. Hontz, L. Sun, C. H. Hendon, A. Walsh, T. Van Voorhis, M. Dinca, J. Am. Chem. Soc., 2015, 137, 1774.
L. E. Darago, M. L. Aubrey, C. J. Yu, M. I. Gonzalez, J. R. Long, J. Am. Chem. Soc., 2015, 137, 15703.
S. Takaishi, M. Hosoda, T. Kajiwara, H. Miyasaka, M. Yamashita, Y. Nakanishi, Y. Kitagawa, K. Yamaguchi, A. Kobayashi, H. Kitagawa, Inorg. Chem., 2009, 48, 9048.
N. S. Meiries, S. P. Nolan, Synlett, 2014, 25, 393.
A. Paulovicova, U. El-Ayaan, K. Shibayama, T. Morita, Y. Fukuda, Eur. J. Inorg. Chem., 2001, 2641.
I. L. Fedushkin, A. A. Skatova, O. V. Eremenko, M. Hummert, H. Schumann, Z. Anorg. Allg. Chem., 2007, 633, 1739.
D. N. Coventry, A. S. Batsanov, A. E. Goeta, J. A. K. Howard, T. B. Marder, Polyhedron, 2004, 23, 2789.
I. L. Fedushkin, A. A. Skatova, S. Y. Ketkov, O. V. Eremenko, A. V. Piskunov, G. K. Fukin, Angew. Chem., Int. Ed., 2007, 46, 4302.
V. A. Klimova, Osnovnye mikrometody analiza organicheskikh soedinenii [Main Micromethods of Analysis of Organic Compounds], Khimiya, Moscow, 1975, 224 pp. (in Russian).
Data Collection, Reduction and Correction Program, CrysAlisPro 1.171.38.46 - Software Package, Rigaku OD, 2015.
Bruker SAINT Data Reduction and Correction Program v. 8.38A, Bruker AXS. Madison, Wisconsin, USA, 2017.
G. M. Sheldrick, SHELXTL. Version 6.14. Structure Determination Software Suite, Madison, Wisconsin, USA, Bruker AXS, 2003.
SCALE3 ABSPACK: Empirical absorption correction, CrysAlisPro 1.171.38.46 - Software Package, Rigaku OD, 2015.
G. M. Sheldrick, SADABS v. 2016/2, Bruker/Siemens Area Detector Absorption Correction Program, Bruker AXS. Madison, Wisconsin, USA, 2016.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 0125–0131, January, 2020.
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Sokolov, V.G., Moskalev, M.V., Koptseva, T.S. et al. New functionalized acenaphthene-1,2-diimines and derived zinc and copper complexes. Russ Chem Bull 69, 125–131 (2020). https://doi.org/10.1007/s11172-020-2733-7
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DOI: https://doi.org/10.1007/s11172-020-2733-7