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Bis(1-naphthylimino)acenaphthene: Redox Properties and One-Electron Reduction

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Abstract

Redox properties of bis(1-naphtylimino)acenaphthene have been studied using various voltammetry techniques. Radical anion of diimine ligand has been obtained in situ through electrochemical reduction, and its optical properties have been studied. A new sodium complex having the anion-radical form of bis(1-naphthylimino)-acenaphthene has been obtained and structurally characterized. We have found that the solvent nature affects the long-wavelength absorption band of the sodium complex, which is determined by the contribution of the coordinated solvent molecules to the lowest unoccupied molecular orbital (LUMO) energy.

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REFERENCES

  1. Yakub, A.M., Moskalev, M.V., Bazyakina, N.L., and Fedushkin, I.L., Russ. Chem. Bull., 2018, vol. 67, pp. 473–478. https://doi.org/10.1007/s11172-018-2095-6

    Article  CAS  Google Scholar 

  2. Bernauer, J., Pölker, J., and Jacobi von Wangelin, A., ChemCatChem, 2022, vol. 14, e202101182. https://doi.org/10.1002/cctc.202101182

    Article  CAS  Google Scholar 

  3. Wang, J., Soo, H.S., and Garcia, F., Commun. Chem., 2020, vol. 3, p. 113. https://doi.org/10.1038/s42004-020-00359-0

    Article  CAS  Google Scholar 

  4. Fedushkin, I.L., Maslova, O.V., Morozov, A.G., Dechert, S., Demeshko, S., and Meyer, F., Angew. Chem., Int. Ed., vol. 51, pp. 10584–10587. https://doi.org/10.1002/anie.201204452

  5. Fedushkin, I.L., Maslova, O.V., Baranov, E.V., and Shavyrin, A.S., Inorg. Chem., 2009, vol. 48, pp. 2355–2357. https://doi.org/10.1021/ic900022s

    Article  CAS  Google Scholar 

  6. Fedushkin, I.L., Skatova, A.A., Chudakova, V.A., and Fukin, G.K., Angew. Chem., Int. Ed., 2003, vol. 42, pp. 3294–3298. https://doi.org/10.1002/anie.200351408

    Article  CAS  Google Scholar 

  7. Moskalev, M.V., Razborov, D.A., Koptseva, T.S., Skatova, A.A., Rumyantcev, R.V., and Fedushkin, I.L., J. Struct. Chem., 2020, vol. 61, pp. 309–315. https://doi.org/10.1134/S002247662002016X

    Article  CAS  Google Scholar 

  8. Moskalev, M.V., Razborov, D.A., Skatova, A.A., Bazanov, A.A., and Fedushkin, I.L., Eur. J. Inorg. Chem., 2021, vol. 2021, pp. 458–463. https://doi.org/10.1002/ejic.202000909

    Article  CAS  Google Scholar 

  9. Rosa, V., Avilés, T., Aullon, G., Covelo, B., and Lodeiro, C., Inorg. Chem., 2008, vol. 47, pp. 7734–7744. https://doi.org/10.1021/ic800790u

    Article  CAS  Google Scholar 

  10. Vigan, M., Ferretti, F., Caselli, A., Ragaini, F., Rossi, M., Mussini, P., and Macchi, P., Chem.-Eur. J., 2014, vol. 20, pp. 14451–14464. https://doi.org/10.1002/chem.201403594

    Article  CAS  Google Scholar 

  11. Cardona, C.M., Li, W., Kaifer, A.E., Stockdale, D., and Bazan, G.C., Adv. Mater., 2011, vol. 23, pp. 2367–2371. https://doi.org/10.1002/adma.201004554

    Article  CAS  Google Scholar 

  12. Hasan, K. and Zysman-Colman, E., J. Phys. Org. Chem., 2013, vol. 26, pp. 274–279. https://doi.org/10.1002/poc.3081

    Article  CAS  Google Scholar 

  13. Fedushkin, I.L., Skatova, A.A., Chudakova, V.A., Cherkasov, V.K., Fukin, G.K., and Lopatin, M.A., Eur. J. Inorg. Chem., 2004, vol. 2004, pp. 388–393. https://doi.org/10.1002/ejic.200300351

    Article  CAS  Google Scholar 

  14. Sheldrick, G.M., Acta Crystallogr., 2015, vol. 71, pp. 3–8. https://doi.org/10.1107/S2053273314026370

    Article  CAS  Google Scholar 

  15. Sheldrick, G.M., Acta Crystallogr., 2007, vol. 64, pp. 112–122. https://doi.org/10.1107/S0108767307043930

    Article  CAS  Google Scholar 

  16. Macrae, C.F., Edgington, P.R., McCabe, P., Pidcock, E., Shields, G.P., Taylor, R., Towler, M., and van de Streek, J., J. Appl. Crystallogr., 2006, vol. 39, pp. 453–457. https://doi.org/10.1107/S002188980600731X

    Article  CAS  Google Scholar 

  17. 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., Peralta, J., Ogliaro, J.E.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, Revision B.01, Gaussian, Inc., Wallingford CT, 2016.

  18. Becke, A.D., J. Chem. Phys., 1993, vol. 98, pp. 5648–5652. https://doi.org/10.1063/1.464913

    Article  CAS  Google Scholar 

  19. Lee, C., Yang, W., and Parr, R.G., Phys. Rev., 1988, p. 785. https://doi.org/10.1103/PhysRevB.37.785

  20. Hehre, W.J., Ditchfield, R., and Pople, J.A., J. Chem. Phys., 1972, vol. 56, pp. 2257–2261. https://doi.org/10.1063/1.1677527

    Article  CAS  Google Scholar 

  21. Hariharan, P.C. and Pople, J.A., Theor. Chim. Acta, 1973, vol. 28, pp. 213–222. https://doi.org/10.1007/BF00533485

    Article  CAS  Google Scholar 

  22. Clark, T., Chandrasekhar, J., Spitznagel, G.W., and Schleyer, P.v.R., J. Comput. Chem., 1983, vol. 4, pp. 294–301. https://doi.org/10.1002/jcc.540040303

    Article  CAS  Google Scholar 

  23. Frisch, M.J., Pople, J.A., and Binkley, J.S., J. Chem. Phys., 1984, vol. 80, p. 3265. https://doi.org/10.1063/1.447079

    Article  CAS  Google Scholar 

  24. Yanai, T., Tew, D., and Handy, N., Chem. Phys. Lett., 2004, vol. 393, pp. 51–57. https://doi.org/10.1016/j.cplett.2004.06.011

    Article  CAS  Google Scholar 

  25. Schäfer, A., Huber, C., and Ahlrichs, R., J. Chem. Phys., 1994, vol. 100, pp. 5829–5835. https://doi.org/10.1063/1.467146

    Article  Google Scholar 

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ACKNOWLEDGMENTS

Authors gratefully acknowledge to Assigned Spectral-Analytical Center of FRC Kazan Scientific Center of RAS for providing necessary facilities to carry out physical-chemical measurements.

Funding

This study was funded by the Russian Science Foundation, project no. 21-73-10186.

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Authors and Affiliations

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

    V. V. Khrizanforova, T. P. Gerasimova, V. I. Morozov, D. R. Islamov & Yu. H. Budnikova

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  1. V. V. Khrizanforova
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  2. T. P. Gerasimova
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  3. V. I. Morozov
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  4. D. R. Islamov
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Correspondence to V. V. Khrizanforova.

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The paper is submitted to special issue titled Free Radicals in Academic and Applied Chemistry.

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Khrizanforova, V.V., Gerasimova, T.P., Morozov, V.I. et al. Bis(1-naphthylimino)acenaphthene: Redox Properties and One-Electron Reduction. Dokl Phys Chem 505, 89–94 (2022). https://doi.org/10.1134/S0012501622600164

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