Skip to main content
SpringerLink
Log in

Synthesis, spectral luminescent properties, and photostability of monoiodo- and dibromo-substituted BF2-dipyrrinates

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

Abstract

4-Iodo-, 4,4′-, and 5,5′-dibromo-substituted BF2-dipyrrinates (BODIPY) have been prepared, and their spectral luminescent properties and photostability have been studied. It has been shown that the introduction of iodine and bromine atoms in the molecule structure results in build-up of the BODIPY phosphorescence and decrease in their fluorescence quantum yield. Basing on the obtained data, the prepared dipyrrinates can be recommended for development of fluorescent sensors for medical and technical applications.

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

Similar content being viewed by others

References

  1. Boyer, J.H., Haag, A.M., Sathyamoorthi, G., Soong, M.L., Thangaraj, K., and Pavlopoulos, T., Heteroatom Chem., 1993, vol. 4, p. 39. DOI: 10.1002/XK.520040107.

    Article  CAS  Google Scholar 

  2. Ra, C., Xu, X., Raymond, S.B., Ferrara, B.J., Neal, K., Bacskai, B.J., Medarova, Z., and Moore, A., J. Am. Chem. Soc., 2009, vol. 31, p. 15257. DOI: 10.1021/ja9047043.

    Google Scholar 

  3. Awuah, S.G., Polreis, J., Biradar, V., and You, Org. Lett., 2011, vol. 13, p. 3884. DOI: 10.1021/ol2014076.

    Article  CAS  Google Scholar 

  4. Pang, W., Zhang, X.F., Zhou, J., Yu, C., Hao, E., and Jio, L., Chem. Commun., 2012, vol. 48, p. 5437. DOI: 10.1039/C2CC30915G.

    Article  CAS  Google Scholar 

  5. Takatoshi, Y., Urano, Y., Mizushima, A., Sunahara, H., Inoue, T., Hirose, K., Iino, M., Kikuchi, K., and Nagan, T., Proc. Nat. Acad. Sci. USA, 2008, vol. 105, p. 28. DOI: 10.1073pnas. 0611717105.

    Article  Google Scholar 

  6. Lim, S., Thivierge, C., Nowak-Sliwinska, P., Han, J., Van den Bergh, H., Wagnieres, G., Burgess, K., and Lee, H., J. Med. Chem., 2010, vol. 53, p. 2865. DOI: 10.1021/jm901823u.

    Article  CAS  Google Scholar 

  7. Hui, H., Pui-Chi, L., Sin-Lui, Y., and Wing-Ping, F.D., Chem. Commun., 2011, vol. 47, p. 4748. DOI: 10.1039/c1cc10727e.

    Article  Google Scholar 

  8. Atilgan, S., Ekmekci, Z., Dogan, A., Guc, D., and Akkaya, E., Chem. Commun., 2006, p. 4398. DOI: 10.1039/b612347c.

    Google Scholar 

  9. Xian-Fu Zhang and Xudong Yang, J. Phys. Chem., 2013, vol. 117, p. 5533. DOI: 10.1021/jp4013812.

    Article  Google Scholar 

  10. Chen, Y., Zhao, J., Xie, L., Guo, H., and Li, Q., RSC Adv., 2012, vol. 2, p. 3942. DOI: 10.1039/C2RA01064J.

    Article  CAS  Google Scholar 

  11. Ortiz, M.J., Agarrabeitia, A.R., Duran-Sampedro, G., Banuelos Prieto, J., Arbeloa Lopez, T., Massad, W.A., Montejano, H.A., Garcia, N.A., and Arbeloa Lopez, I., Tetrahedron, 2012, vol. 68, p. 1153. DOI: 10.1016/j.tet.2011.11.070.

    Article  CAS  Google Scholar 

  12. Duman, S., Cakmak, Y., Kolemen, S., Akkaya, E.U., and Dede, Y., J. Org. Chem., 2012, vol. 77, p. 4516. DOI: 10.1021/jo300051v.

    Article  CAS  Google Scholar 

  13. Qin, W., Baruah, M., Auweraer, M.V., Schryver, F.C., and Boens, N.J., Phys. Chem. A., 2005, vol. 109, p. 7371. DOI:10.1021/jp052626n.

    Article  CAS  Google Scholar 

  14. Jiao, L., Pang, W., Zhou, J., Wei, Y., Mu, X., Bai, G., and Hao, E., J. Org. Chem., 2011, vol. 76, p. 9988. DOI: 10.1021/jo201754m.

    Article  CAS  Google Scholar 

  15. Zhang, X., Yu, H., and Xiao, Y., J. Org. Chem., 2012, vol. 77, p. 669. DOI: 10.1021/jo201413b.

    Article  CAS  Google Scholar 

  16. Chromic Materials, Phenomena and their Technological Applications. Applied Science Innovations, Somani, P.R., Ed., Amsterdam: Elsevier, 2012, p. 641.

  17. Lakshmi, V. and Ravikanth, M., Dalton Trans., 2012, vol. 41, p. 5903. DOI: 10.1039/c2dt00019a.

    Article  CAS  Google Scholar 

  18. Aksenova, Yu.V., Kuznetsova, R.T., Yutanova, S.L., and Berezin, M.B., Izv. Vuzov, Fizika, 2012, vol. 55, p. 90.

    Google Scholar 

  19. Kuznetsova, R.T., Aksenova, Yu.V., Solodova, T.A., Bashkirtsev, D.E., Kopylova, T.N., Tel’minov, E.N., Mayer, G.V., Berezin, M.B., Semeikin, A.S., Yutanova, S.L., Antina, E.V., Arabei, S.M., Pavich, T.A., and Solovyov, K.N., Optics and Spectroscopy, 2013, vol. 115, p. 708. DOI: 10.1134/S0030400X13110118.

    Article  CAS  Google Scholar 

  20. Yutanova, S.L., Kuznetsova, R.T., Aksenova, Yu.V., Telminov, E.N., and Berezin, M.B., Russ. Phys. J., 2013, vol. 56, no. 3, p. 264. DOI: 10.1007/s11182-013-0025-5.

    Article  CAS  Google Scholar 

  21. Guseva, G.B., Antina, E.V., Berezin, M.B., Semeikin, A.S., and V’yugin, A.I., Russ. J. Gen. Chem., 2002, vol. 72, no. 1, p. 126. DOI: 10.1023/A:1015318017581.

    Article  CAS  Google Scholar 

  22. Pozdnyakov, I.P., Aksenova, Yu.V., Ermolina, E.G., Melnikov, A.A., Kuznetsova, R.T., Grivin, V.P., Plyusnin, V.F., Berezin, M.B., Semeikin, A.S., and Chekalin, S.V., Chem. Phys. Lett., 2013, vol. 585, p. 49. DOI: 10.1016/j.cplett.2013.08.032.

    Article  CAS  Google Scholar 

  23. Ermolina, E.G., Kuznetsova, R.T., Aksenova, Yu.V., Gadirov, R.M., Kopylova, T.N., Antina, E.V., Berezin, M.B., and Semeikin, A.S., Sensors and Actuators (B), 2014, vol. 197, p. 206.

    Article  CAS  Google Scholar 

  24. Solomonov, A.V., Rumyantsev, E.V., Kochergin, B.A., and Antina, E.V., Russ. J. Phys. Chem. (A), 2012, vol. 86, p. 1048. DOI: 10.1134/S0036024412070266.

    Article  CAS  Google Scholar 

  25. Chernova, O.M., Berezin, M.B., and Antina, E.V., Russ. J. Phys. Chem. (A), 2003, vol. 77, p. 896.

    Google Scholar 

  26. Lebedeva, N.Sh., Antina, E.V., Berezin, M.B., Semeikin, A.S., and Bukushina, G.B., Russ. J. Phys. Chem. (A), 2000, vol. 74., C. 1039.

    Google Scholar 

  27. Kuznetsova, R., Aksenova, Yu., Telminov, E., Samsonova, L., Mayer, G., Kopylova, T., Antina, E., Yutanova, S., Berezin, M., and Guseva, G., Optics and Spectroscopy, 2012, vol. 112, p. 746. DOI: 10.1134/S0030400X12050104.

    Article  CAS  Google Scholar 

  28. Lakowicz, J.R., Principles of Fluorescence Spectroscopy, Springer, 1983.

    Book  Google Scholar 

  29. Fischer, M. and Georges, J., Chem. Phys. Lett., 1996, vol. 260, p. 115.

    Article  CAS  Google Scholar 

  30. Terenin, A.N., Fotonika molekul krasitelei (Photonics of Molecules of Dye), Leningrad: Nauka, 1968, p. 100.

    Google Scholar 

  31. Qin, W., Barauh, M., Van der Auweraer, M., De Schryver, F.C., and Boens, N., J. Phys. Chem. (A), 2005, vol. 109, no. 33, p. 7371. DOI: 10.1021/jp052626n.

    Article  CAS  Google Scholar 

  32. Guseva, G.B., Antina, E.V., Berezen, M.B., V’yugin, A.I., and Nuraneeva, E.N., Russ. J. Gen. Chem., 2013, vol. 83, no. 8, p. 1571. DOI: 10.1134/S1070363213080161.

    Article  CAS  Google Scholar 

  33. Gordon, A.J. and Ford, R.A., The Chemist’s Companion. A Handbook of Practical Data, Techniques and References, New York: Wiley, 1972.

    Google Scholar 

  34. Clezy, P.S. and Liepa, A.J., J. Aust. Chem., 1970, vol. 23, p. 2641. DOI: 10.1071/CH9702461.

    Google Scholar 

  35. Berezen, M.B., Semeikin, A.S., and V’yugin, A.I., Zh. Fiz. Khim, 1996, vol. 70, p. 1364.

    Google Scholar 

  36. Ytanova, C.L., Berezin, M.B., Semeikin, A.S., Antina, E.V., Guseva, G.B., and V’yugin, A.I., Russ. J. Gen. Chem., 2013, vol. 83, no. 3, p. 545. DOI: 10.1134/S1070363213030237.

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Krestov Institute of Solutions Chemistry, Russian Academy of Sciences, ul. Akademicheskaya 1, Ivanovo, 153045, Russia

    E. N. Nuraneeva, G. B. Guseva, E. V. Antina, M. B. Berezin & A. I. V’yugin

  2. National Research Tomsk State University, Tomsk, Russia

    R. T. Kuznetsova

Authors
  1. E. N. Nuraneeva
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. G. B. Guseva
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. E. V. Antina
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. R. T. Kuznetsova
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. M. B. Berezin
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. A. I. V’yugin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to E. N. Nuraneeva.

Additional information

Original Russian Text © E.N. Nuraneeva, G.B. Guseva, E.V. Antina, R.T. Kuznetsova, M.B. Berezin, A.I. V’yugin, 2016, published in Zhurnal Obshchei Khimii, 2016, Vol. 86, No. 4, pp. 653–660.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Nuraneeva, E.N., Guseva, G.B., Antina, E.V. et al. Synthesis, spectral luminescent properties, and photostability of monoiodo- and dibromo-substituted BF2-dipyrrinates. Russ J Gen Chem 86, 840–847 (2016). https://doi.org/10.1134/S1070363216040149

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363216040149

Keywords

Search

Navigation