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Synthesis, structure, and photoluminescence properties of N-{2-[5-(2-hydroxyphenylmethyleneamino)-1-alkylbenzimidazol-2-yl]phenyl}-4-methylbenzenesulfamides and their zinc complexes

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Abstract

N-{2-[5-(2-Hydroxyphenylmethyleneamino)-1-alkylbenzimidazol-2-yl]phenyl}-4-methyl-benzenesulfamides (H2L) and their zinc complexes Zn2L2 were synthesized. The structure of the ligands and complexes was studied by IR, UV, 1Н NMR, X-ray absorption spectroscopy, and X-ray diffraction analysis. The complexes show green photoluminescence (λfl = 492 nm) with quantum yields φ = 0.07–0.17.

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References

  1. Wright, J.B., Chem. Rev., 1951, vol. 48, p. 397.

    Article  CAS  Google Scholar 

  2. Comprehensive Coordination Chemistry II, McCleverty, J.A. and Meyer, T.J., Eds., Amsterdam: Elsevier, 2004, vol. 1, p. 125.

  3. Comprehensive Heterocyclic Chemistry III, Katritzky, A.R., Ramsden, C.A., Scriven, E.F.V., and Taylor, R.J.K., Eds., Amsterdam: Elsevier, 2008, vol. 4, p. 143.

  4. Khalafi-Nezhad, A., Soltani Rad, M.N., Mohabatkar, H., Asrari, Z., and Hemmateenejad, B., Bioorg. Med. Chem., 2005, vol. 13, no. 6, p. 1931. doi 10.1016/j.bmc.2005.01.014

    Article  CAS  Google Scholar 

  5. Shingalapur, R.V., Hosamani, K.M., and Keri, R.S., Eur. J. Med. Chem., 2009, vol. 44, no. 10, p. 4244. doi 10.1016/j.ejmech.2009.05.021

    Article  CAS  Google Scholar 

  6. White, A.W., Curtin, N.J., Eastman, B.W., Golding, B.T., Hostomsky, Z., Kyle, S., Li, J., Maegley, K.A., Skalitzky, D.J., Webber, S.E., Yu, X.-H., and Griffin, R.J., Bioorg. Med. Chem. Lett., 2004, vol. 14, no. 10, p. 2433. doi 10.1016/j.bmcl.2004.03.017

    Article  CAS  Google Scholar 

  7. Garnovskii, A.D., Sadimenko, A.P., Vasilchenko, I.S., Garnovskii, D.A., Sennikova, E.V., and Minkin, V.I., Adv. Heterocycl. Chem., 2009, vol. 97, p. 291. doi 10.1016/S0065-2725(08)00205-5

    Article  CAS  Google Scholar 

  8. Wu, H., Sun, T., Li, K., Xu, Y., Yun, R., and Sun, Q., Z. Anorg. Allg. Chem., 2009, vol. 635, p. 146. doi 10.1002/zaac.200800346

    Article  CAS  Google Scholar 

  9. Minkin, V.I., Tsivadze, A.Yu., Burlov, A.C., Vannikov, A.V., Garnovskii, A.D., Dmitriev, A.V., Lypenko, D.A., Mal’tsev, E.I., Metelitsa, A.V., Vasil’chenko, I.S., and Garnovskii, D.A., RF Patent 2408648, 2011; Byull. Izobret., 2011, no. 1.

  10. Burlov, A.C., Mal’tsev, E.I., Dmitriev, A.V., Lypenko, D.A., Pozin, S.I., Vannikov, A.V., Garnovskii, D.A., Koshchienko, Yu.V., Metelitsa, A.V., Tsivadze, A.Yu., and Minkin, V.I., RF Patent 2532565, 2014; Byull. Izobret., 2014, no. 31.

  11. Yakushhenko, I.K., Kaplunov, M.G., and Krasnikova, S.S., RF Patent 2368641, 2009; Byull. Izobret., 2009, no. 27.

  12. Krasnikova, S.S., Kaplunov, M.G., and Yakushchenko, I.K., High Energy Chem., 2009, vol. 43, no. 7, p. 536. doi 10.1134/S0018143909070054

    Article  CAS  Google Scholar 

  13. Krasnikova, S.S., Yakushchenko, I.K., Shamaev, S.N., and Kaplunov, M.G., Mol. Cryst. Liq. Cryst., 2007, vol. 468, p. 87. doi 10.1080/15421400701229511.

    Article  Google Scholar 

  14. Sano, T., Nishio, Y., Hamada, Y., Takahashi, H., and Usuki, T., J. Mater. Chem., 2000, vol. 10, no. 1, p. 157. doi 10.1039/A903239H

    Article  CAS  Google Scholar 

  15. Chen, L., Qiao, J., Xie, J., Duan, L., Zhang, D., Wang, L., Qiu, Y., and Chen, L., Inorg. Chim. Acta, 2009, vol. 362, no. 7, p. 2327. doi 10.1016/j.ica.2008.10.016

    Article  CAS  Google Scholar 

  16. Pivovarov, A.P., Kaplunov, M.G., Yakushchenko, I.K., Belov, M.Yu., Nikolaeva, G.V., and Efimov, O.N., Russ. Chem. Bull., 2002, vol. 51, no. 1, p. 67. doi 10.1023/A:1015053512033

    Article  CAS  Google Scholar 

  17. Kaplunov, M.G., Yakushchenko, I.K., Krasnikova, S.S., Shamaev, S.N., Pivovarov, A.P., and Efimov, O.N., Russ. Chem. Bull., 2004, vol. 53, no. 10, p. 2148. doi 10.1007/s11172-005-0088-8

    Article  CAS  Google Scholar 

  18. Yakushchenko, I.K., Kaplunov, M.G., Shamaev, S.N., Efimov, O.N., Nikolaeva, G.V., Belov, M.Yu., Pivovarov, A.P., Skvortsov, A.G., and Voronina, V.A., RF Patent 2155204, 2000; Byull. Izobret., 2000, no. 24.

  19. Xie, J., Qiao, J., Wang, L., Xie, J., and Qiu, Y., Inorg. Chim. Acta, 2005, vol. 358, no. 15, p. 4451. doi 10.1016/j.ica.2005.08.018

    Article  CAS  Google Scholar 

  20. Lyssenko, K.A., Borissova, A.O., Burlov, A.S., Vasilchenko, I.S., Garnovskii, A.D., Minkin, V.I., and Antipin, M.Yu., Mendeleev Commun., 2007, vol. 17, no. 3, p. 164. doi 10.1016/j.mencom.2007.05.011

    Article  CAS  Google Scholar 

  21. Burlov, A.S., Lyssenko, K.A., Koshchienko, Yu.V, Nikolaevskii, S.A., Vasilchenko, I.S., Garnovskii, D.A., Uraev, A.I., and Garnovskii, A.D., Mendeleev Commun., 2008, vol. 18, no. 4, p. 198. doi 10.1016/j.mencom.2008.07.009

    Article  CAS  Google Scholar 

  22. Nikolaevskii, S.A., Kiskin, M.A., Koshchienko, Yu.V., Burlov, A.S., Makarova, N.I., Starikov, A.G., and Eremenko, I.L., Crystallogr. Rep., 2013, vol. 58, no. 3, p. 437. doi 10.1134/S1063774513030164

    Article  CAS  Google Scholar 

  23. Burlov, A.S., Koshchienko, Yu.V., Kiskin, M.A., Nikolaevskii, S.A., Garnovskii, D.A., Lermontov, A.S., Makarova, N.I., Metelitsa, A.V., and Eremenko, I.L., J. Mol. Struct., 2016, vol. 1104, p. 7. doi 10.1016/j.molstruc.2015.07.056

    Article  CAS  Google Scholar 

  24. Parker, C.A., Photoluminescence of Solutions. With Applications to Photochemistry and Analytical Chemistry, New York Elsevier Publishing Company, 1968.

    Google Scholar 

  25. Krasovitskii, B.M. and Bolotin, B.M., Organicheskie lyuminofory (Organic Luminophores), Moscow Khimiya, 1984.

    Google Scholar 

  26. Chernyshov, A.A., Veligzhanin, A.A., and Zubavichus, Y.V., Nucl. Instr. Meth. Phys. Res. (A), 2009, vol. 603, p. 95. doi 10.1016/j.nima.2008.12.16

    Article  CAS  Google Scholar 

  27. Kochubei, D.I., Babanov, Yu.A., Zamaraev, K.I., Vedrinskii, R.V., Kraizman, V.L., Kulipanov, G.N., Mazalov, L.N., Skrinskii, A.N., Fedorov, V.I., Khel’mer, B.Yu., and Shuvaev, A.T., Rentgenospektral’nyi metod izucheniya struktury amorfnykh tel: EXAFS-spektroskopiya (X-Ray Spectral Method for Studying the Structure of Amorphous Solids: EXAFSSpectroscopy), Novosibirsk Nauka, Sib. Otd., 1988.

    Google Scholar 

  28. Newville, M., J. Synchrotron Rad., 2001, no. 8, p. 96. doi 10.1107/S0909049500016290

    Article  CAS  Google Scholar 

  29. Zabinsky, S.I., Rehr, J.J., Ankudinov, A., Albers, R.C., and Eller, M.J., Phys. Rev. (B), 1995, vol. 52, p. 2995. doi 10.1103/PhysRevB.52.2995

    Article  CAS  Google Scholar 

  30. SMART (control) and SAINT (integration) Software. Version 5.0. Madison (WI, USA): Bruker AXS Inc., 1997.

  31. Sheldrick, G.M., SADABS. Program for Scanning and Correction of Area Detector Data. Göttinngen, Germany, University of Göttingen, 2004.

    Google Scholar 

  32. Sheldrick, G.M., Acta Crystallogr. (A), 2008, vol. 64, p. 112. doi 10.1107/S0108767307043930

    Article  CAS  Google Scholar 

  33. Burlov, A.S., Ikorskii, V.N., Nikolaevskii, S.A., Koshchienko, Yu.V., Vlasenko, V.G., Zubavichus, Ya.V., Uraev, A.I., Vasilchenko, I.S., Garnovskii, D.A., Borodkin, G.S., and Garnovskii, A.D., Russ. J. Inorg. Chem., 2008, vol. 53, p. 1566. doi 10.1134/S0036023608100082

    Article  Google Scholar 

  34. Chernova, N.I., Ryabokobylko, Yu.S., Brudz’, V.G., and Bolotin, B.M., Zh. Org. Khim., 1971, vol. 7, no. 8, p. 1680.

    CAS  Google Scholar 

  35. Nikolaevskii, S.A., Koshchienko, Yu.V., Chernyshev, A.V., Burlov, A.S., Cheprasov, A.S., Aleksandrov, G.G., Kiskin, M.A., and Metelitsa, A.V., Russ. J. Coord. Chem., 2014, vol. 40, p. 468. doi 10.1134/S1070328414070070

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Institute of Physical and Organic Chemistry of Southern Federal University, pr. Stachki 194/2, Rostov-on-Don, 344090, Russia

    Yu. V. Koshchienko, A. S. Burlov, N. I. Makarova, A. V. Metelitsa & V. I. Minkin

  2. Institute of Physics of Southern Federal University, Rostov-on-Don, Russia

    V. G. Vlasenko

  3. N.S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Moscow, Russia

    S. A. Nikolaevskii, M. A. Kiskin & G. G. Alexandrov

  4. Southern Scientific Centre Academy of Sciences, Rostov-on-Don, Russia

    D. A. Garnovskii

Authors
  1. Yu. V. Koshchienko
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  2. A. S. Burlov
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  3. N. I. Makarova
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  4. V. G. Vlasenko
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  5. S. A. Nikolaevskii
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  6. M. A. Kiskin
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  8. D. A. Garnovskii
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  9. A. V. Metelitsa
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  10. V. I. Minkin
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Corresponding author

Correspondence to A. S. Burlov.

Additional information

Original Russian Text © Yu.V. Koshchienko, А.S. Burlov, N.I. Makarova, V.G. Vlasenko, S.А. Nikolaevskii, М.А. Kiskin, G.G. Alexandrov, D.А. Garnovskii, А.V. Metelitsa, V.I. Minkin, 2017, published in Zhurnal Obshchei Khimii, 2017, Vol. 87, No. 1, pp. 80–89.

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Koshchienko, Y.V., Burlov, A.S., Makarova, N.I. et al. Synthesis, structure, and photoluminescence properties of N-{2-[5-(2-hydroxyphenylmethyleneamino)-1-alkylbenzimidazol-2-yl]phenyl}-4-methylbenzenesulfamides and their zinc complexes. Russ J Gen Chem 87, 76–85 (2017). https://doi.org/10.1134/S1070363217010133

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