Self assembly of a novel Cu(II) complex, (C6H9N2)2[CuCl4]: experimental, computational, and molecular docking survey

Abstract

In the title salt complex (C6H9N2)2[CuCl4] symbolized along this work by (2A5PCuCl4), the Cu2+ cation is coordinated by four chloride anions and adopts a distorted tetrahedral geometry. This compound has been crystallized in the monoclinic space group C2/c and the following parameters obtained are a = 13.0244(19) Å, b = 8.3149(11) Å, c = 16.001(2) Å, β = 93.730(6)°, Z = 4, V = 1729.2(4) Å3 at 150 K. In the crystal structure, the atomic arrangement consists of isolated tetrahedral entities connected to the organic groups by weak hydrogen bonds N–H…Cl and C–H…Cl forming a three-dimensional network. The Hirshfeld surface analysis shows on two-dimensional fingerprints maps the great dominance of H…Cl and H…H contacts in the crystal packaging. The geometrical optimization, electronic, topological and biological properties of 2A5PCuCl4 were theoretically studied using DFT. The HOMO and LUMO analysis are used to decide the charge transfer within the structure. Natural bond orbital analysis was carried out to study hyperconjugative interactions. Optical transmission measurements investigated by UV–visible and photoluminescence spectroscopy are carried out on a crystalline thin-film of 2A5PCuCl4 show the detection of two absorption bands centered at 316 and 519 nm coherent with those observed in the perovskites based on CuCl4. Photoluminescence measurements showed two peaks at around 433 and 472 nm. The unaided-eye-detectable blue luminescence emission comes from the excitonic transition in the CuCl4 anions.

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References

  1. 1.

    K.K. Bisht, A.C. Kathalikkattil, S. Eringathodi, J. Mol. Struct. 1013, 102 (2012)

    CAS  Article  Google Scholar 

  2. 2.

    K. Edwards, S.N. Herringer, A.R. Parent, M. Provost, K.C. Shortsleeves, M.M. Turnbull, L.N. Dawe, Inorg. Chem. Acta 368, 141 (2011)

    CAS  Article  Google Scholar 

  3. 3.

    H. Adams, D. Bradshaw, D.E. Fenton, Polyhedron 21, 1957 (2002)

    CAS  Article  Google Scholar 

  4. 4.

    Y. Yamamoto, T. Yoshida, T. Suzuki, S. Kaizaki, Inorg. Chim. Acta 325, 187 (2001)

    CAS  Article  Google Scholar 

  5. 5.

    N. Lah, R. Clérac, Polyhedron 28, 2466 (2009)

    CAS  Article  Google Scholar 

  6. 6.

    B.J. Prince, M.M. Turnbull, R.D. Willett, J. Coord. Chem. 56, 441 (2003)

    CAS  Article  Google Scholar 

  7. 7.

    S.N. Herringer, M.M. Turnbull, C.P. Landee, J.L. Wikaira, J. Coord. Chem. 62, 863 (2009)

    CAS  Article  Google Scholar 

  8. 8.

    X.H. Zhu, N. Mercier, P. Frere, P. Blanchard, J. Roncali, M. Allain, C. Pasquier, A. Riou, Inorg. Chem. 42, 5330 (2003)

    CAS  PubMed  Article  Google Scholar 

  9. 9.

    M. Bujak, J. Zaleski. Cryst. Eng. 4, 241 (2001)

    CAS  Article  Google Scholar 

  10. 10.

    K. Karoui, A.B. Rhaiem, K. Guidara, Phys. B 407, 489 (2012)

    CAS  Article  Google Scholar 

  11. 11.

    D.B. Mitzi, K. Chondroudis, C.R. Kagan, IBM J. Res. Dev. 45, 29 (2001)

    CAS  Article  Google Scholar 

  12. 12.

    C.R. Kagan, D.B. Mitzi, C. Dimitrakopoulos, Science 286, 945 (1999)

    CAS  PubMed  Article  Google Scholar 

  13. 13.

    P. Zhou, J.E. Drumheller, Phys. Rev. 45, 12365 (1992)

    CAS  Article  Google Scholar 

  14. 14.

    R. Willett, H. Place, M. Middleton, J. Am. Chem. Soc. 110, 8639 (1988)

    CAS  Article  Google Scholar 

  15. 15.

    P. Ghalsasi, N. Garg, M.N. Deo, A. Garg, H. Mande, P.S. Ghalsasi, S.M. Sharma, Phys. Chem. Chem. Phys. 17, 32204 (2015)

    CAS  PubMed  Article  Google Scholar 

  16. 16.

    S.F. Haddad, M.A. AlDamen, R.D. Willett, Inorg. Chim. Acta 359, 424 (2006)

    CAS  Article  Google Scholar 

  17. 17.

    C.C. Becerra, A. Paduan-Folho, J. Magn. Magn. Mater. 267, 244 (2003)

    CAS  Article  Google Scholar 

  18. 18.

    A.R. Parent, C.P. Landee, M.M. Turnbull, Inorg. Chim. Acta 360, 1943 (2007)

    CAS  Article  Google Scholar 

  19. 19.

    M.A. Ahmed, S.T. Bishay, M.A. Gabal, N. Helmy, J. Mater. Sci. 40, 411 (2005)

    CAS  Article  Google Scholar 

  20. 20.

    B. W. Stewart, P. Kleihues, World cancer report (2003).

  21. 21.

    P. Anand, A.B. Kunnumakara, C. Sundaram, K.B. Harikumar, S.T. Tharakan, O.S. Lai, B. Sung, B.B. Aggarwal, Pharm. Res. 25, 2097 (2008)

    CAS  PubMed  PubMed Central  Article  Google Scholar 

  22. 22.

    P.M. Clare, R.A. Poorman, L.C. Kelley, K.D. Watenpaugh, C.A. Bannow, K.L. Leach, J. Biol. Chem. 276, 48292 (2001)

    CAS  PubMed  Article  Google Scholar 

  23. 23.

    S.A. Jackson, S. Sahni, L. Lee, Y. Luo, T.R. Nieduzak, G. Liang, Y. Chiang, N. Collar, D. Fink, W. He, A. Laoui, J. Merrill, R. Boffey, P. Crackett, B. Rees, M. Wong, J.-P. Guilloteau, M. Mathieu, S.S. Rebello, Bioorg. Med. Chem. 13, 2723 (2005)

    CAS  PubMed  Article  Google Scholar 

  24. 24.

    B. Coupez, R.A. Lewis, Curr. Med. Chem. 13, 2995 (2006)

    CAS  PubMed  Article  Google Scholar 

  25. 25.

    M. Berry, B. Fielding, J. Gamieldien, Emerging trends in computational biology, bioinformatics, and systems biology, in Practical Considerations in Virtual Screening and Molecular Docking (2015).

  26. 26.

    Bruker, APEX2, SAINT and SADABS, Bruker AXS Inc., Madison, Wisconsin, USA (2006).

  27. 27.

    A. Altomare, M.C. Burla, M. Camalli, G.L. Cascarano, C. Giacovazzo, A. Guagliardi, A.G.G. Moliterni, G. Polidori, R. Spagna, J. Appl. Cryst. 32, 115 (1999)

    CAS  Article  Google Scholar 

  28. 28.

    G.M. Sheldrick, Acta Cryst. C71, 3 (2015)

    Google Scholar 

  29. 29.

    L.J. Farrugia, J. Appl. Cryst. 45, 849 (2012)

    CAS  Article  Google Scholar 

  30. 30.

    K. Brandenburg, Diamond Version 2.0 Impact (GbR, Bonn, 1998).

    Google Scholar 

  31. 31.

    S.K. Wolff, D.J. Grimwood, J.J. McKinnon, D. Jayatilaka, M.A. Spackman, Crystal Explorer 3.1 (University of Western Australia, Perth, 2013).

    Google Scholar 

  32. 32.

    M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, O. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, D.J. Fox, GAUSSIAN 09, Revision A.02 (Gaussian, Inc., Wallingford, CT, 2009).

    Google Scholar 

  33. 33.

    R.I. Dennington, T. Keith, J. Millam, GaussView, Version 5.0.8 (Semichem. Inc, Shawnee Mission, KS, 2008).

    Google Scholar 

  34. 34.

    E.D. Glendening, J.K. Badenhoop, A.D. Reed, J.E. Carpenter, F. Weinhold, NBO 3.1 (Theoretical Chemistry Institute, University of Wisconsin, , Madison, WI, 1996).

    Google Scholar 

  35. 35.

    E. Runge, E.K.U. Gross, Phys. Rev. Lett. 52, 997 (1984)

    CAS  Article  Google Scholar 

  36. 36.

    W. Humphrey, A. Dalke, K. Schulten, J. Mol. Graph. 14, 33 (1996)

    CAS  PubMed  PubMed Central  Article  Google Scholar 

  37. 37.

    J.-M. Yang, C.-C. Chen, GEMDOCK: a generic evolutionary method for molecular docking proteins. Struct. Funct. Bioinform. 55, 288 (2004)

    CAS  Article  Google Scholar 

  38. 38.

    E. Kose, A. Atac, F. Bardak, J. Mol. Struct. 1163, 147 (2018)

    CAS  Article  Google Scholar 

  39. 39.

    J. Bernstein, R.E. David, L. Shimoni, N.-L. Chang, Angew Chem. Int. Ed. Engl. 34, 1555 (1995)

    CAS  Article  Google Scholar 

  40. 40.

    R.H. Al-Far, B.F. Ali, Acta Cryst. E65, m73 (2009)

    Google Scholar 

  41. 41.

    A. Kessentini, M. Belhouchet, J.J. Suñol, Y. Abid, T. Mhiri, J. Lumin. 149, 341 (2014)

    CAS  Article  Google Scholar 

  42. 42.

    L. Yang, D.R. Powell, R.P. Houser, R. Soc. Chem. Dalton Trans. 9, 955 (2007)

    Article  Google Scholar 

  43. 43.

    M. Tahenti, S. Gatfaoui, N. Issaoui, T. Roisnel, H. Marouani, J. Mol. Struct. 1207, 127781 (2020)

    CAS  Article  Google Scholar 

  44. 44.

    W. Ben Hmida, A. Jellali, H. Abid, B. Hamdi, H. Naili, R. Zouari, J. Mol. Struct. 1184, 604 (2019)

    CAS  Article  Google Scholar 

  45. 45.

    S.K. Seth, G.C. Maity, T. Kar, J. Mol. Struct. 1000, 120 (2011)

    CAS  Article  Google Scholar 

  46. 46.

    J.L. Wardell, M.M. Jotani, E.R.T. Tieking, Acta Cryst. E72, 1691 (2016)

    Google Scholar 

  47. 47.

    E.R. Johnson, S. Keinan, P. Mori-Sánchez, J. Contreras-García, A.J. Cohen, W. Yang, J. Am. Chem. Soc. 132, 6498 (2010)

    CAS  PubMed  PubMed Central  Article  Google Scholar 

  48. 48.

    S. Gatfaoui, N. Issaoui, A. Mezni, F. Bardak, T. Roisnel, A. Atac, H. Marouani, J. Mol. Struct. 1150, 242 (2017)

    CAS  Article  Google Scholar 

  49. 49.

    S. Gatfaoui, N. Issaoui, S.A. Brandan, T. Roisnel, H. Marouani, J. Mol. Struct. 1151, 152 (2018)

    CAS  Article  Google Scholar 

  50. 50.

    Z. Xiao, H. Chen, M. Shi, G. Wu, R. Zhou, Z. Yang, M. Wang, B. Tang, Mater. Sci. Eng. B 117, 313 (2005)

    Article  CAS  Google Scholar 

  51. 51.

    W. Wang, X. Chen, S. Efrima, Chem. Mater. 11, 1883 (1999)

    CAS  Article  Google Scholar 

  52. 52.

    T. Yoshinari, T. Nanba, S. Shinamuki, S. Shimanuki, M. Fujisawa, R. Aoyagi, J. Phys. Soc. Jpn. 61, 2224 (1992)

    CAS  Article  Google Scholar 

  53. 53.

    S. Kitagawa, R. Kitaura, S. Noro, Angew. Chem. Int. Ed. 43, 2334 (2004)

    CAS  Article  Google Scholar 

  54. 54.

    A. Kessentini, M. Belhouchet, Y. Abid, C. Minot, T. Mhiri, Spectrochem. Acta Part A 122, 476 (2014)

    CAS  Article  Google Scholar 

  55. 55.

    B.J. McConkey, V. Sobolev, M. Edelman, Curr. Sci. 83, 845 (2002)

    CAS  Google Scholar 

  56. 56.

    T.J.A. Ewing, I.D. Kuntz, J. Comput. Chem. 18, 1175 (1997)

    CAS  Article  Google Scholar 

  57. 57.

    D.J. Wood, S. Korolchuk, N.J. Tatum, L.Z. Wang, J.A. Endicott, M.E. Noble, M.P. Martin, Cell Chem. Biol. 26, 121 (2019)

    CAS  PubMed  PubMed Central  Article  Google Scholar 

  58. 58.

    L. Gopinathan, S.L.W. Tan, V.C. Padmakumar, V. Coppola, L. Tessarollo, P. Kaldis, Cancer Res. 74, 3870 (2014)

    CAS  PubMed  PubMed Central  Article  Google Scholar 

  59. 59.

    T.O. Fischmann, A. Hruza, J.S. Duca, L. Ramanathan, T. Mayhood, W.T. Windsor, H.V. Le, T.J. Guzi, M.P. Dwyer, K. Paruch, R.J. Doll, E. Lees, D. Parry, W. Seghezzi, V. Madison, Biopolym. Orig. Res. Biomol. 89, 372 (2008)

    CAS  Google Scholar 

  60. 60.

    X.-J. Chu, W.D. Pinto, D. Bartkovitz, S.-S. So, B.T. Vu, K. Packman, C. Lukacs, Q. Ding, N. Jiang, K. Wang, P. Goelzer, X. Yin, M.A. Smith, B.X. Higgins, Y. Chen, Q. Xiang, J. Moliterni, G. Kaplan, B. Graves, A. Lovey, N. Fotouhi, J. Med. Chem. 49, 6549 (2006)

    CAS  PubMed  Article  Google Scholar 

  61. 61.

    W.F. De Azevedo, S. Leclerc, L. Meijer, L. Havlicek, M. Strnad, S.-H. Kim, Eur. J. Biochem. 243, 518 (1997)

    PubMed  Article  Google Scholar 

  62. 62.

    T. Midtvedt, Side Eff. Drugs Annu. 31, 413 (2009)

    Article  Google Scholar 

  63. 63.

    E.D. Garcin, A.S. Arvai, R.J. Rosenfeld, M.D. Kroeger, B.R. Crane, G. Andersson, G. Andrews, P.J. Hamley, P.R. Mallinder, D.J. Nicholls, S.A. St-Gallay, A.C. Tinker, N.P. Gensmantel, A. Mete, D.R. Cheshire, S. Connolly, D.J. Stuehr, A. Åberg, A.V. Wallace, J.A. Tainer, E.D. Getzoff, Nat. Chem. Biol. 4, 700 (2008)

    CAS  PubMed  PubMed Central  Article  Google Scholar 

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Acknowledgements

The authors would like to thank the Ministry of Higher Education and Scientific Research of Tunisia.

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Gatfaoui, S., Issaoui, N., Noureddine, O. et al. Self assembly of a novel Cu(II) complex, (C6H9N2)2[CuCl4]: experimental, computational, and molecular docking survey. J IRAN CHEM SOC (2021). https://doi.org/10.1007/s13738-021-02195-y

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Keywords

  • Cu(II) complex
  • X-ray diffraction
  • RDG
  • HOMO–LUMO
  • Fluorescence
  • Molecular docking