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Synthesis of 1,3-diketo derivatives of calix[4]arene with nonyl substituents at the lower rim as novel efficient sensibilizers of Tb3+ luminescence

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Abstract

Novel bis- and tetra-1,3-diketo derivatives of calix[4]arene with nonyl substituents at the lower rim have been synthesized. Their conformational and tautomeric composition have been determined; spectral parameters and complex formation properties with Tb3+ have been studied. Substitution of two 1,3-diketo groups with bromine under going from tetra- to bis 1,3-diketone derivatives was resulted in twofold increase luminescence intensity in their terbium complexes. Lifetime of the excited state of the terbium luminescence of the corresponding complexes as well as lifetime of excited triplet level of the 1,3-diketonate ligands have been determined.

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References

  1. Sekhar, B.Ch., J. Heterocycl. Chem., 2004, vol. 41, p. 807. doi 10.1002/jhet.5570410601

    Article  CAS  Google Scholar 

  2. Attanasi, O., Filippone, P., Mei, A., Serra-Zanetti, F., Synth. Commun., 1986, vol. 16, p. 343. doi 10.1080/00397918608076316

    Article  CAS  Google Scholar 

  3. Kumar, V., Aggarwal, R., and Singh, S.P., Heterocycles 2008, vol. 75, p. 2893. doi 10.3987/REV-08-634

    Article  CAS  Google Scholar 

  4. Atta, K.F.M., Farahat, O.O.M., Al-Shargabi, T.Q., Marei, M.G., and El Ashry, E.S.H., ChemInform., 2015, vol. 46, p. 67. doi 10.1002/chin.201525256

    Article  Google Scholar 

  5. Pradhan, J. and Goyal, A., Int. J. Pharm. Res. Appl. Sci., 2015, vol. 4, no. 2, p. 1.

    Google Scholar 

  6. Bray, D.J., Clegg, J.K., Lindoy, L.F., and Schilter, D., Adv. Inorg. Chem., 2007, vol. 59, p. 1. doi 10.1016/S0898-8838(06)59001-4

    CAS  Google Scholar 

  7. Arkhipova, A.A., Tsysin, G.I., Statkus, M.A., Bol’-shov, M.A., Seregina, I.F., and Zolotov, Y.A., Talanta, 2016, vol. 161, p. 497. doi 10.1016/j.talanta.2016.08.074

    Article  CAS  Google Scholar 

  8. Binnemans, K., Gschneidner, K.A., Bünzli, J.-C.G., and Pecharsky, V.K., Handbook on the Physics and Chemistry of Rare Earths, North Holland: Elsevier Science, 2005, vol. 35, p. 107.

    Article  Google Scholar 

  9. Whan, A.R.E. and Crosby, G.A., J. Mol. Spectrosc., 1962, vol. 8, p. 315. doi 10.1016/0022-2852(62)90031-0

    Article  CAS  Google Scholar 

  10. Bassett, A.P., Magennis, S.W., Glover, P.B., Lewis, D.J., Spencer, N., Parsons, S., Williams, R.M., De Cola, L., and Pikramenou, Z.J., J. Am. Chem. Soc., 2004, vol. 126, no. 30, p. 9413. doi 10.1021/ja048022z

    Article  CAS  Google Scholar 

  11. Otway, D.J. and Rees, W.S., Coord. Chem. Rev., 2000, vol. 210, p. 279. doi 10.1016/S0010-8545(00)00360-X

    Article  CAS  Google Scholar 

  12. Pettinari, C., Marchetti, F., and Drozdov, A., Compr. Coord. Chem., 2004, vol. 1, p. 97. doi 10.1016/B0-08-043748-6/01181-6

    CAS  Google Scholar 

  13. Cativiela, C., Serrano, J.L., and Zurbano, M.M., J. Org. Chem., 1995, vol. 60, no. 10, p. 3074. doi 10.1021/jo00115a023

    Article  CAS  Google Scholar 

  14. Aromí, G., Gamez, P., and Reedijk, J., Coord. Chem. Rev., 2008, vol. 252, p. 964. doi 10.1016/j.ccr.2007.07.008

    Article  Google Scholar 

  15. Vigato, P.A., Peruzzo, V., and Tamburini, S., Coord. Chem. Rev., 2009, vol. 253, p. 1099. doi 10.1016/j.ccr.2008.07.013

    Article  CAS  Google Scholar 

  16. Kogan, K. and Biali, S., J. Org. Chem., 2009, vol. 74, p. 7172. doi 10.1021/jo901450x

    Article  CAS  Google Scholar 

  17. Kogan, K., Columbus, I., and Biali, S., J. Org. Chem., 2008, vol. 73, p. 7327. doi 10.1021/jo801187z

    Article  CAS  Google Scholar 

  18. Itzhak, N., Kogan, K., and Biali, S.E., Eur. J. Org. Chem., 2011, p. 6581. doi 10.1002/ejoc.201100779

    Google Scholar 

  19. Fujimoto, K. and Shinkai, S., Tetrahedron Lett., 1994, vol. 35, p. 2915. doi 10.1016/S0040-4039(00)76659-7

    Article  CAS  Google Scholar 

  20. Shamsutdinova, N.A., Podyachev, S.N., Sudakova, S.N., Mustafina, A.R., Zairov, R.R., Burilov, V.A., Nizameev, I.R., Rizvanov, I.K., Syakaev, V.V., Gabidullin, B.M., Katsuba, S.A., Gubaidullin, A.T., Safiullin, G.M., and Dehaen, W., New, J. Chem., 2014, vol. 38, p. 4130. doi 10.1039/c4nj00637b

    Article  CAS  Google Scholar 

  21. Zairov, R., Shamsutdinova, N., Podyachev, S., Sudakova, S., Gimazetdinova, G., Rizvanov, I., Syakaev, V., Babaev, V., Amirov, R., and Mustafina, A., Tetrahedron, 2016, vol. 72, p. 2447. doi 10.1016/j.tet.2016.03.068

    Article  CAS  Google Scholar 

  22. Podyachev, S.N., Sudakova, S.N., Gimazetdinova, G.Sh., Shamsutdinova, N.A., Syakaev, V.V., Barsukova, T.A., Iki, N., Lapaev, D.V., and Mustafina, A.R., New. J. Chem., 2017, vol. 41, p. 1526. doi 10.1039/c6nj03381d

    Article  CAS  Google Scholar 

  23. Podyachev, S.N., Sudakova, S.N., Galiev, A.K., Mustafina, A.R., Syakaev, V.V., Shagidullin, R.R., Bauer, I., and Konovalov, A.I., Russ. Chem. Bull., 2006, vol. 55, p. 2000. doi 10.1007/s11172-006-0542-2

    Article  CAS  Google Scholar 

  24. Albrecht, M., Osetska, O., Klankermayer, J., Fröhlich, R., Gumyd, F., and Bünzli, J.-C.G., Chem. Commun., 2007, p. 1834. doi 10.1039/b618918k

    Google Scholar 

  25. Charles, R.G., Org. Synth., 1959, vol. 39, p. 61. doi 10.15227/orgsyn.039.0061

    Article  CAS  Google Scholar 

  26. Pearson, R.G. and Mayerle, E.A., J. Am. Chem. Soc., 1951, vol. 73, p. 926. doi 10.1021/ja01147a012

    Article  CAS  Google Scholar 

  27. Bray, D.J., Jolliffe, K.A., Lindoy, L.F., and McMurtrie, J.C., Tetrahedron, 2007, vol. 63, p. 1953. doi 10.1016/j.tet.2006.12.071

    Article  CAS  Google Scholar 

  28. Becker, H.G.O., Organikum, Organisch-Chemisches Grundpraktikum, Deutscher Verlag der Wissenschaften, Leipzig, 1993.

    Google Scholar 

  29. Staniszewski, B. and Urbaniak, W., Chem. Papers, 2009, vol. 63, no. 2, p. 212. doi 10.2478/s11696-008-0097-9

    Article  CAS  Google Scholar 

  30. Schűhle, D.T., Klimosch, S., and Schatz, J., Tetrahedron Lett., 2008, vol. 49, p. 5800. doi 10.1016/j.tetlet.2008.07.128

    Article  Google Scholar 

  31. Jaime, C., De Mendoza, J., Prados, P., Nieto, P.M., and Sanchez, C., J. Org. Chem., 1991, vol. 56, p. 3372. doi 10.1021/jo00010a036

    Article  CAS  Google Scholar 

  32. Crosby, G.A., Whan, R.E., and Alire, R.M., J. Chem. Phys., 1961, vol. 34, p. 743. doi 10.1063/1.1731670

    Article  CAS  Google Scholar 

  33. Latva, M., Takalo, H., Mukkala, V.-M., Matachescu, C., Rodriguez-Ubis, J.C., and Kankare, J., J. Lumin., 1997, vol. 75, p. 149. doi 10.1016/S0022-2313(97)00113-0

    Article  CAS  Google Scholar 

  34. Steemers, F.J., Verboom, W., Reinhoudt, D.N., Van Der Tal, E.B., and Verhoeven, J.W., J. Am. Chem. Soc., 1995, vol. 117, p. 9408. doi 10.1021/ja00142a004

    Article  CAS  Google Scholar 

  35. Handbook of Photochemistry, Murov, S.L., Carmichael, I., and Hug, G.L., Eds., New York: Marcel Dekker, Inc., 1993.

  36. Sager, W.F., Filipescu, N., and Serafin, F.A., J. Phys. Chem., 1965, vol. 69, p. 1092. doi 10.1021/j100888a002

    Article  CAS  Google Scholar 

  37. Sivchik, V.V., Solomatina, A.I., Chen, Y.-T., Karttunen, A.J., Tunik, S.P., Chou, P.-T., and Koshevoy, I.O., Angew. Chem. Int. Ed., 2015, vol. 54, p. 14057. doi 10.1002/anie.201507229

    Article  CAS  Google Scholar 

  38. He, Y., Liu, L., Zhang, Z., Fu, G., Lü, X., Wong, W.-K., and Jones, R.A., Inorg. Chem. Commun., 2016, vol. 64, p. 13. doi 10.1016/j.inoche.2015.12.012

    Article  CAS  Google Scholar 

  39. Tong, G.S.M., Chow, P.K., and Che, C.-M., Angew. Chem. Int. Ed., 2010, vol. 49, p. 9206. doi 10.1002/anie.201004601

    Article  CAS  Google Scholar 

  40. Sun, C.-L., Li, J., Geng, H.-W., Li, H., Ai, Y., Wang, Q., Pan, S.-L., and Zhang, H.-L., Chem. Asian J., 2013, vol. 8, p. 3091. doi 10.1002/asia.201300732

    Article  CAS  Google Scholar 

  41. Lapaev, D.V., Nikiforov, V.G., Safiullin, G.M., Galyaviev, I.G., Dzabarov, V.I., Knyazev, A.A., Lobkov, V.S., and Galyametdinov, Y.G., J. Struct. Chem., 2009, vol. 50, p. 775. doi 10.1007/s10947-009-0117-9

    Article  CAS  Google Scholar 

  42. Gutsche, C.D., Levine, J.A., and Sujeeth, P.K., J. Org. Chem., 1985, vol. 50, p. 5802. doi 10.1021/jo00350a072

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, ul. Akademika Arbuzova 8, Kazan, Tatarstan, 420029, Russia

    S. N. Podyachev, S. N. Sudakova & V. V. Syakaev

  2. Kazan National Research Institute of Technology, Kazan, Tatarstan, Russia

    G. Sh. Gimazetdinova & R. N. Nagimov

  3. Zavoiskii Kazan Physico-Technical Institute, Kazan Scientific Center, Russian Academy of Sciences, Kazan, Tatarstan, Russia

    D. V. Lapaev

Authors
  1. S. N. Podyachev
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  2. G. Sh. Gimazetdinova
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  4. D. V. Lapaev
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  5. V. V. Syakaev
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Correspondence to S. N. Podyachev.

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Dedicated to V. F. Mironov on His 60th Anniversary

Original Russian Text © S.N. Podyachev, G.Sh. Gimazetdinova, S.N. Sudakova, D.V. Lapaev, V.V. Syakaev, R.N. Nagimov, 2017, published in Zhurnal Obshchei Khimii, 2017, Vol. 87, No. 9, pp. 1476–1486.

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Podyachev, S.N., Gimazetdinova, G.S., Sudakova, S.N. et al. Synthesis of 1,3-diketo derivatives of calix[4]arene with nonyl substituents at the lower rim as novel efficient sensibilizers of Tb3+ luminescence. Russ J Gen Chem 87, 1958–1968 (2017). https://doi.org/10.1134/S1070363217090110

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  • DOI: https://doi.org/10.1134/S1070363217090110

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