Skip to main content
Log in

New functionalized acenaphthene-1,2-diimines and derived zinc and copper complexes

  • Full Article
  • Published:
Russian Chemical Bulletin Aims and scope

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. 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.

    Article  CAS  Google Scholar 

  2. D. M. D’Alessandro, Chem. Commun., 2016, 52, 8957.

    Article  Google Scholar 

  3. C. Pettinari, F. Marchetti, N. Mosca, G. Tosia, A. Drozdov, Polym. Int., 2017, 66, 731.

    Article  CAS  Google Scholar 

  4. S. Kitagawa, S. Kawata, Coord. Chem. Rev., 2002, 224, 11.

    Article  CAS  Google Scholar 

  5. Z. Zhang, H. Yoshikawa, K. Awaga, J. Am. Chem. Soc., 2014, 136, 16112.

    Article  CAS  Google Scholar 

  6. T. C. Narayan, T. Miyakai, S. Seki, M. Dinca, J. Am. Chem. Soc., 2012, 134, 12932.

    Article  CAS  Google Scholar 

  7. 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.

    Article  CAS  Google Scholar 

  8. L. E. Darago, M. L. Aubrey, C. J. Yu, M. I. Gonzalez, J. R. Long, J. Am. Chem. Soc., 2015, 137, 15703.

    Article  CAS  Google Scholar 

  9. 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.

    Article  CAS  Google Scholar 

  10. N. S. Meiries, S. P. Nolan, Synlett, 2014, 25, 393.

    CAS  Google Scholar 

  11. A. Paulovicova, U. El-Ayaan, K. Shibayama, T. Morita, Y. Fukuda, Eur. J. Inorg. Chem., 2001, 2641.

    Google Scholar 

  12. I. L. Fedushkin, A. A. Skatova, O. V. Eremenko, M. Hummert, H. Schumann, Z. Anorg. Allg. Chem., 2007, 633, 1739.

    Article  CAS  Google Scholar 

  13. D. N. Coventry, A. S. Batsanov, A. E. Goeta, J. A. K. Howard, T. B. Marder, Polyhedron, 2004, 23, 2789.

    Article  CAS  Google Scholar 

  14. 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.

    Article  CAS  Google Scholar 

  15. V. A. Klimova, Osnovnye mikrometody analiza organicheskikh soedinenii [Main Micromethods of Analysis of Organic Compounds], Khimiya, Moscow, 1975, 224 pp. (in Russian).

    Google Scholar 

  16. Data Collection, Reduction and Correction Program, CrysAlisPro 1.171.38.46 - Software Package, Rigaku OD, 2015.

  17. Bruker SAINT Data Reduction and Correction Program v. 8.38A, Bruker AXS. Madison, Wisconsin, USA, 2017.

  18. G. M. Sheldrick, SHELXTL. Version 6.14. Structure Determination Software Suite, Madison, Wisconsin, USA, Bruker AXS, 2003.

    Google Scholar 

  19. SCALE3 ABSPACK: Empirical absorption correction, CrysAlisPro 1.171.38.46 - Software Package, Rigaku OD, 2015.

  20. G. M. Sheldrick, SADABS v. 2016/2, Bruker/Siemens Area Detector Absorption Correction Program, Bruker AXS. Madison, Wisconsin, USA, 2016.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to A. A. Skatova.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 0125–0131, January, 2020.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

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

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-020-2733-7

Key words

Navigation