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Physico-chemical and theoretical investigation of the Schiff’s base of 2,6-diformyl-4-tert-butylphenol and m-aminocinnamic acid

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Abstract

Novel bis-azomethine, the product of condensation of 2,6-diformyl-4-tert-butylphenol and m-aminocinnamic acid, has been synthesized. The product structure and properties have been investigated by means of 1Н NMR, IR, and electronic spectroscopy as well as quantum-chemical simulation. Potential application of the bis-azomethine as a component of dye sensitized solar cells has been demonstrated.

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References

  1. Ohno, K., Arima, K., Tanaka, S., Yamagata, T., Tsurugi, H., and Masima, K., Organimetallics, 2009, vol. 28, no. 11, p. 3256. DOI: 10.1021/om900043u.

    Article  CAS  Google Scholar 

  2. Mukherjee, S., Weyhemuller, T., Bothe, E., Wieghardt, K., and Chaudhuri, P., Eur. J. Inorg. Chem., 2003, vol. 2003, no. 5, p. 863. DOI: 10.1002/ejic.200390116.

    Article  Google Scholar 

  3. Jones, M.D., Davidson, M.G., Keir, C.G., Hughes, L.M., Mahon, M.F., and Aperely, D.C., Eur. J. Inorg. Chem., 2009, vol. 2009, no. 5, p. 635. DOI: 10.1002/ejic.200801049.

    Article  Google Scholar 

  4. Han, L.-Q., Sun, W.-H., Wang, L.-Y., Shao, C.-X., Wang, H.-G., and Li, J.-T., Chin. J. Chem., 2002, vol. 20, no. 12, p. 1523. DOI: 10.1002/cjoc.20020201212.

    Article  CAS  Google Scholar 

  5. Du, J., Han, L., Cui, Y., Li, J., Li, Y., and Sun, W.-H., Austr. J. Chem., 2003, vol. 56, no. 7, p. 703. DOI: 10.1071/CH02193.

    Article  CAS  Google Scholar 

  6. Visinescu, D., Madalan, A., Kravtsov, V., Simonov, Y., Schmidtmann, M., Muller, A., and Andruh, M., Polyhedron, 2003, vol. 22, no. 10, p. 1385. DOI: 10.1016/S0277-5387(03)00113-X.

    Article  CAS  Google Scholar 

  7. Borisova, N., Reshetova, M., Magdesieva, T., Khrustalev, V., Skazov, R., Dolganov, A., Ikorskiy, V., Novotortsev, V., Eremenko, I., Moiseev, I., and Ustynyuk, Y., Inorg. Chim. Acta, 2008, vol. 361, p. 2032. DOI: 10.1016/jica.2007.10.020.

    Article  CAS  Google Scholar 

  8. Okawa, H. and Kida, S., Bull. Chem. Soc. Japan, 1972, vol. 45, p. 2480. DOI: 10.1246/bcsj.45.2480.

    Article  CAS  Google Scholar 

  9. Herman, J. and Erxlelen, A., Inorg. Chim. Acta, 2000, vol. 304, p. 125. DOI: S0020169300000645.

    Article  Google Scholar 

  10. Okawa, H., Kida, S., Muto, Y., and Tokii, T., Bull. Chem. Soc. Japan, 1972, vol. 45, no. 8, p. 2480. DOI: 10.1246/bcsj.45.2480.

    Article  CAS  Google Scholar 

  11. Al-Sehemi, A.G., Irfan, A., Asiri, A.M., and Ammar, Y.A., J. Mol. Struct., 2012, vol. 1019, p. 130. DOI: 10.1016/jmolstruc.2012.02.035.

    Article  CAS  Google Scholar 

  12. Hagfeld, A.T, Boschloo, G., Sun, L., Kloo, L., and Pettersson, H., Chem. Rev., 2010, vol. 110, p. 6595. DOI: 10.1021/cr900356p.

    Article  Google Scholar 

  13. Chantal, D., Coord. Chem. Rev., 2015, vol. 282, p. 19. DOI: 10.1016/jccr.2014.05.023.

    Google Scholar 

  14. Zhang, L. and Cole, J.M., ACS Appl. Mater. Interfaces, 2015, vol. 7, no. 6, p. 3427. DOI: 10.1021/am507334m.

    Article  CAS  Google Scholar 

  15. Linoy, L.F., Meehan, G.V., and Svenstrup, N., Synthesis, 1998, no. 7, p. 1029. DOI: 10.1055/s-1998- 2110.

    Article  Google Scholar 

  16. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Montgomery, J.A., Vreven, Jr. T., Kudin, K.N., Burant, J.C., Millam, J.M., Iyengar, S.S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G.A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J.E., Hratchian, H.P., Cross, J.B., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Ayala, P.Y., Morokuma, K., Voth, G.A., Salvador, P., Dannenberg, J.J., Zakrzewski, V.G., Dapprich, S., Daniels, A.D., Strain, M.C., Farkas, O., Malick, D.K., Rabuck, A.D., Raghavachari, K., Foresman, J.B., Ortiz, J.V., Cui, Q., Baboul, A.G., Clifford, S., Cioslowski, J., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C.Y., Nanayakkara, A., Challacombe, M., Gill, P.M.W., Johnson, B., Chen, W., Wong, M.W., Gonzalez, C., and Pople, J.A., Gaussian 03, Revision E.1., 2003.

    Google Scholar 

  17. Stephens, P.J., Devlin, F.J., Chabalowski, C.F., and Frisch, M.J., J. Phys. Chem., 1994, vol. 98, p. 11623. DOI: 10.1021/j100096a001.

    Article  CAS  Google Scholar 

  18. Becke, A.D., J. Chem. Phys., 1993, vol. 98, p. 5648. DOI: 10.1063/1.464913.

  19. Lee, C., Yang, W., and Parr, R.G., Phys. Rev. B, 1988, vol. 37, p. 785. DOI: 10.1103/PhysRevB.37.785.

    Article  CAS  Google Scholar 

  20. Tsipis, A.C., Coord. Chem. Rev., 2014, vol. 272, p. 1. DOI: 10.1016/jccr.2014.02.023.

    Article  CAS  Google Scholar 

  21. Wang, Y.-G., J. Phys. Chem. A, 2009, vol. 113, no. 41, p. 10867. DOI: 10.1021/jp904007j.

    Article  CAS  Google Scholar 

  22. Furche, F. and Rappoport, D., Theoretical and Computational Chemistry, Elsevier, 2005, vol. 16, p. 93. DOI: 10.1016/S1380-7323(05)80020-2.

    Article  CAS  Google Scholar 

  23. Miertus, S., Scrocco, E., and Tomasi, J., Chem. Phys., 1981, vol. 55, p. 117. DOI: 10.1016/0301-0104(81)85090-2.

    Article  CAS  Google Scholar 

  24. Cammi, R. and Tomasi, J., J. Comput. Chem., 1995, vol. 16, p. 1449. DOI: 10.1002/jcc.540161202.

    Article  CAS  Google Scholar 

  25. Gorelsky, S.I., SWizard Program, Version 4.6, University of Ottawa, Canada, 2010. http://wwwsgchem. net/swizard.

    Google Scholar 

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Correspondence to A. A. Tsaturyan.

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Original Russian Text © A.A. Tsaturyan, L.D. Popov, Yu.P. Tupolova, I.N. Shcherbakov, O. I. Askalepova, V.V. Lukov, S.I. Levchenkov, A.A. Zubenko, V.A. Kogan, 2015, published in Zhurnal Obshchei Khimii, 2015, Vol. 85, No. 11, pp. 1818–1825.

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Tsaturyan, A.A., Popov, L.D., Tupolova, Y.P. et al. Physico-chemical and theoretical investigation of the Schiff’s base of 2,6-diformyl-4-tert-butylphenol and m-aminocinnamic acid. Russ J Gen Chem 85, 2560–2567 (2015). https://doi.org/10.1134/S1070363215110092

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  • DOI: https://doi.org/10.1134/S1070363215110092

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