Skip to main content
SpringerLink
Log in

Non-Covalent Interactions in Weak Donor–Acceptor Systems Based on Toluene and Tetracyanoquinodimethane Derivatives

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

A series of 1 : 1 cocrystals of weak donor–acceptor complexes between toluene and fluorinated derivatives of tetracyanoquinodimethane with alternating donor and acceptor components has been obtained. Mutual orientation of the donor and acceptor molecules in the stacks is similar to the geometry of supramolecular dimers corresponding to the energy minimum, according DFT simulation of the pairwise interactions. Thus, despite the fact that the energy of the π–π interactions has not exceeded 4 kcal/mol, they are highly important for the supramolecular organization of the donor and acceptor components in the cocrystals. Due to small size of the donor, the crystal packing is mainly determined by weak lateral interactions involving the acceptor molecules and is strongly dependent on the number of fluorine atoms. The charge transfer is estimated using the QTAIM method and does not exceed 0.06e.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1.
Fig. 2.
Fig. 3.
Fig. 4.
Fig. 5.
Fig. 6.
Fig. 7.

Similar content being viewed by others

REFERENCES

  1. Jiang, H., Hu, P., Ye, J., Zhang, K.K., Long, Y., Hu, W., and Kloc, C., J. Mater. Chem. (C), 2018, vol. 6, no. 8, p. 1884. https://doi.org/10.1039/C7TC04982J

    Article  CAS  Google Scholar 

  2. Goetz, K.P., Vermeulen, D., Payne, M.E., Kloc, C., McNeil, L.E., and Jurchescu, O.D., J. Mater. Chem. (C), 2014, vol. 2, no. 17, p. 3065. https://doi.org/10.1039/C3TC32062F

    Article  CAS  Google Scholar 

  3. Wang, C., Dong, H., Jiang, L., and Hu, W., Chem. Soc. Rev., 2018, vol. 47, no. 2, p. 422. https://doi.org/10.1039/C7CS00490G

    Article  CAS  Google Scholar 

  4. Krupskaya, Y., Gibertini, M., Marzari, N., and Morpurgo, A.F., Adv. Mater., 2015, vol. 27, no. 15, p. 2453. https://doi.org/10.1002/adma.201405699

    Article  CAS  Google Scholar 

  5. Kataeva, O., Ivshin, K., Metlushka, K., Nikitina, K., Khrizanforova, V., Budnikova, Y., Fayzullin, R.R., Latypov, S., Schiemenz, S., Bretschneider, M., Popov, A., Avdoshenko, S., Krupskaya, Y., Büchner, B., and Knupfer, M., Cryst. Growth Des., 2022, vol. 22, no. 1, p. 751. https://doi.org/10.1021/acs.cgd.1c01255

    Article  CAS  Google Scholar 

  6. Bader, R.F.W., Chem. Rev., 1991, vol. 91, no. 5, p. 893. https://doi.org/10.1021/cr00005a013

    Article  CAS  Google Scholar 

  7. Kataeva, O., Nohr, M., Ivshin, K., Hampel, S., Büchner, B., and Knupfer, M., Cryst. Growth Des., 2021, vol. 21, no. 1, p. 471. https://doi.org/10.1021/acs.cgd.0c01287

    Article  CAS  Google Scholar 

  8. Kataeva, O., Ivshin, K., Metlushka, K., Latypov, S., Nikitina, K., Zakharychev, D., Laskin, A., Alfonsov, V., Sinyashin, O., Mgeladze, E., Jäger, A., Krupskaya, Y., Büchner, B., and Knupfer, M., Cryst. Growth Des., 2019, vol. 19, no. 9, p. 5123. https://doi.org/10.1021/acs.cgd.9b00486

    Article  CAS  Google Scholar 

  9. Armarego, W.L.F. and Chai, C.L.L., Purification of Laboratory Chemicals, Cornwall: Butterworth-Heinernann, 2003, p. 370.

  10. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Petersson, G.A., Nakatsuji, H., Li, X., Caricato, M., Marenich, A.V., Bloino, J., Janesko, B.G., Gomperts, R., Mennucci, B., Hratchian, H.P., Ortiz, J.V., Izmaylov, A.F., Sonnenberg, J.L., Williams-Young, D., Ding, F., Lipparini, F., Egidi, F., Goings, J., Peng, B., Petrone, A., Henderson, T., Ranasinghe, D., Zakrzewski, V.G., Gao, J., Rega, N., Zheng, G., Liang, W., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Throssell, K., Montgomery, J.A.Jr., Peralta, J.E., Ogliaro, F., Bearpark, M.J., Heyd, J.J., Brothers, E.N., Kudin, K.N., Staroverov, V.N., Keith, T.A., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A.P., Burant, J.C., Iyengar, S.S., Tomasi, J., Cossi, M., Millam, J.M., Klene, M., Adamo, C., Cammi, R., Ochterski, J.W., Martin, R.L., Morokuma, K., Farkas, O., Foresman, J.B., and Fox, D.J., Gaussian 16, Rev. A.03, Gaussian, Inc., 2016.

  11. van Duijneveldt, F.B., van Duijneveldt-van de Rijdt, J.G.C.M., and van Lenthe, J.H., Chem. Rev., 1994, vol. 94, no. 7, p. 1873. https://doi.org/10.1021/cr00031a007

    Article  CAS  Google Scholar 

  12. Keith, T.A., AIMAll, Version 10.05.04, Professional, TK Gristmill Software, Overland Park KS, USA, 2010. http://aim.tkgristmill.com/

  13. Espinosa, E., Molins, E., and Lecomte, C., Chem. Phys. Lett., 1998, vol. 285, nos. 3–4, p. 170. https://doi.org/10.1016/S0009-2614(98)00036-0

    Article  CAS  Google Scholar 

  14. APEX3 Crystallography software Suite, Bruker AXS Inc., Madison, WI, USA, 2016.

  15. SAINT, Crystallography software Suite, Bruker AXS Inc., Madison, WI, USA, 2016.

  16. Krause, L., Herbst-Irmer, R., Sheldrick, G.M., and Stalke, D., J. Appl. Crystallogr., 2015, vol. 48, p. 3. https://doi.org/10.1107/S1600576714022985

    Article  CAS  Google Scholar 

  17. Sheldrick, G.M., Acta Crystallogr. (A), 2008, vol. 64, no. 1, p. 112. https://doi.org/10.1107/S0108767307043930

    Article  CAS  Google Scholar 

Download references

Funding

This study was financially supported by the Russian Science Foundation (grant no. 21-13-00220), the measurements have been carried out using the equipment of Distributed Spectral-Analytical Center of Shared Facilities for Study of Structure, Composition and Properties of Substances and Materials of FRC Kazan Scientific Center of RAS.

Author information

Authors and Affiliations

  1. A. E. Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences”, 420088, Kazan, Russia

    K. A. Ivshin, A. P. Fedonin, R. G. Zinnatullin, K. E. Metlushka, S. K. Latypov & O. N. Kataeva

Authors
  1. K. A. Ivshin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. P. Fedonin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. R. G. Zinnatullin
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. K. E. Metlushka
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. S. K. Latypov
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. O. N. Kataeva
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to K. A. Ivshin.

Ethics declarations

The authors declare that they have no conflicts of interest.

Additional information

To the 145th anniversary of A.E. Arbuzov

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ivshin, K.A., Fedonin, A.P., Zinnatullin, R.G. et al. Non-Covalent Interactions in Weak Donor–Acceptor Systems Based on Toluene and Tetracyanoquinodimethane Derivatives. Russ J Gen Chem 92, 2561–2568 (2022). https://doi.org/10.1134/S1070363222120027

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363222120027

Keywords:

Search

Navigation