Skip to main content
Log in

New Fluorescent Materials Based on Polysiloxanes and Boron Bis(β-diketonates)

  • Published:
Polymer Science, Series C Aims and scope Submit manuscript

Abstract

Crosslinked polysiloxanes with boron bis(dibenzoylmethanate) complexes used as crosslink junctions of polymer networks are first synthesized, and their physicochemical, mechanical, thermal, and fluorescent properties are studied. It is shown that the polymers under study feature the elastic behavior, possess high thermal and thermo-oxidative stability, and exhibit intense fluorescence in a wide wavelength range (400‒700 nm).

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1.
Fig. 2.
Fig. 3.
Fig. 4.
Fig. 5.
Fig. 6.
Fig. 7.
Fig. 8.

Similar content being viewed by others

REFERENCES

  1. S. Wei, Z. Li, W. Lu, H. Liu, J. Zhang, T. Chen, and B. Z. Tang, Angew. Chemie Int. Ed. 60, 8608 (2021).

    Article  CAS  Google Scholar 

  2. G. Ahumada and M. Borkowska, Polymers (Basel) 14, 1118 (2022).

    Article  CAS  PubMed  Google Scholar 

  3. S. Cichosz, A. Masek, and M. Zaborski, Polym. Test. 67, 342 (2018).

    Article  CAS  Google Scholar 

  4. C. Calvino, A. Guha, C. Weder, and S. Schrett, Adv. Mater. 30, 1704603 (2018).

  5. X. Du, C. Wang, G. Wu, and S. Chen, Angew. Chemie Int. Ed. 60, 8585 (2021).

    Article  CAS  Google Scholar 

  6. L. Birchall, A. Foerster, G. A. Rance, A. Terry, R. D. Wildman, and C. J. Tuck, Sens. Actuators, A 347, 113977 (2022).

  7. J. Alday, A. Mazzeo, and S. Suarez, Inorg. Chim. Acta 510, 119696 (2020).

  8. P.-Z. Chen, L.-Y. Niu, Y.-Z. Chen, and Q.-Z. Yang, Coord. Chem. Rev. 350, 196 (2017).

    Article  CAS  Google Scholar 

  9. K. Tanaka and Y. Chujo, NPG Asia Mater. 7, e223 (2015).

  10. A. Loudet and K. Burgess, Chem. Rev. 107, 4891 (2007).

    Article  CAS  PubMed  Google Scholar 

  11. D. Frath, J. Massue, G. Ulrich, and R. Ziessel, Angew. Chemie Int. Ed. 53, 2290 (2014).

    Article  CAS  Google Scholar 

  12. D. Li, H. Zhang, and Y. Wang, Chem. Soc. Rev. 42, 8416 (2013).

    Article  CAS  PubMed  Google Scholar 

  13. R. Yoshii, K. Suenaga, K. Tanaka, and Y. Chujo, Chem.-Eur. J. 21, 7231 (2015).

    Article  CAS  PubMed  Google Scholar 

  14. T. Sagawa, F. Ito, A. Sakai, Y. Ogata, K. Tanaka, and H. Ikeda, Photochem. Photobiol. Sci. 15, 420 (2016).

    Article  CAS  PubMed  Google Scholar 

  15. Y. N. Kononevich, M. N. Temnikov, A. A. Korlyukov, A. D. Volodin, P. V. Dorovatovskii, V. A. Sazhnikov, A. A. Safonov, D. S. Ionov, A. A. Ivanov, N. M. Surin, E. A. Svidchenko, and A. M. Muzafarov, ChemPlusChem 85, 1111 (2020).

    Article  CAS  PubMed  Google Scholar 

  16. W. A. Morris, M. Kolpaczynska, and C. L. Fraser, J. Phys. Chem. 120, 22539 (2016).

    Article  CAS  Google Scholar 

  17. M. Louis, C. Piñero García, A. Brosseau, C. Allain, and R. Metivier, J. Phys. Chem. Lett. 10, 4758 (2019).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  18. L. Zhang, L.-L. Ma, X. Wang, and X.-Y. Zhao, J. Lumin. 214, 116560 (2019).

  19. M. Louis, R. Sethy, J. Kumar, S. Katao, R. Guillot, T. Nakashima, C. Allain, T. Kawai, and R. Metivier, Chem. Sci. 10, 843 (2019).

    Article  CAS  PubMed  Google Scholar 

  20. C.-T. Poon, W. H. Lam, H.-L. Wong, and V. W.-W. Yam, J. Am. Chem. Soc. 132, 13992 (2010).

    Article  CAS  PubMed  Google Scholar 

  21. Z. Li, D. Wang, D. Ramella, H. Gao, H. Cao, Y. Zhao, Z. Miao, Z. Yang, and W. He, Polym. Chem. 11, 3046 (2020).

    Article  CAS  Google Scholar 

  22. M. Zhuang, S. Joshi, H. Sun, T. Batabyal, C. L. Fraser, and J. Kapur, Sci. Rep. 11, 1076 (2021).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  23. Z. Li, Y. Pei, S. Hou, Y. Dai, D. Liu, J. Zhu, Y.-P. Zhu, and X. Liu, Dyes Pigm. 179, 108419 (2020).

  24. Y. N. Kononevich, V. A. Sazhnikov, A. S. Belova, A. A. Korlyukov, A. D. Volodin, A. A. Safonov, G. A. Yurasik, D. S. Ionov, and A. M. Muzafarov, New J. Chem. 43, 13725 (2019).

    Article  CAS  Google Scholar 

  25. D. Ionov, G. Yurasik, Y. Kononevich, V. Sazhnikov, A. Muzafarov, and M. Alfimov, Procedia Eng. 168, 341 (2016).

    Article  CAS  Google Scholar 

  26. D. S. Ionov, V. A. Sazhnikov, G. A. Yurasik, A. V. Antonov, Y. N. Kononevich, and M. V. Alfimov, High Energy Chem. 49, 183 (2015).

    Article  CAS  Google Scholar 

  27. N. M. D. Brown and P. Bladon, J. Chem. Soc. A, No. 526, 526 (1969).

  28. G. A. Reynolds and C. H. Chen, J. Heterocycl. Chem. 22, 657 (1985).

    Article  CAS  Google Scholar 

  29. D. Martin, Chem. Rev. 34, 461 (1944).

    Article  CAS  Google Scholar 

  30. W. Gerrard and M. F. Lappert, Chem. Rev. 58, 1081 (1958).

    Article  CAS  Google Scholar 

  31. A. Barabas, E. Isfan, M. Roman, M. Paraschiv, E. Romas, and A. T. Balaban, Tetrahedron 24, 1133 (1968).

    Article  CAS  Google Scholar 

  32. Z. Sui, R. Salto, J. Li, C. Craik, and P. R. Ortiz de Montellano, Bioorg. Med. Chem. 1, 415 (1993).

    Article  CAS  PubMed  Google Scholar 

  33. W.-Y. Shao, Y.-N. Cao, Z.-W. Yu, W.-J. Pan, X. Qiu, X.-Z. Bu, L.-K. An, Z.-S. Huang, L.-Q. Gu, and A. S. C. Chan, Tetrahedron Lett. 47, 4085 (2006).

    Article  CAS  Google Scholar 

  34. L. Shi, L. Gao, S. Cai, Q. Xiong, and Z. Ma, Eur. J. Med. Chem. 221, 113528 (2021).

  35. P. Banet, L. Legagneux, P. Hesemann, J. Moreau, L. Nicole, A. Quach, C. Sanchez, and T. Tranthi, Sens. Actuators, B 130, 1 (2008).

    Article  CAS  Google Scholar 

  36. X. Chen, X. Zhang, and G. Zhang, Chem. Commun. 51, 161 (2015).

    Article  CAS  Google Scholar 

  37. X. Zhang and G. Zhang, Anal. Methods 4, 2641 (2012).

    Article  CAS  Google Scholar 

  38. Y. Liang, L. Xu, F. Qu, K. Tang, H. Wang, and W. W. Yu, Polym. Chem. 10, 4818 (2019).

    Article  CAS  Google Scholar 

  39. I. Toulokhonova, B. Bjerke-Kroll, and R. West, J. Organomet. Chem. 686, 101 (2003).

    Article  CAS  Google Scholar 

  40. A. C. Benniston, G. Copley, A. Harriman, and R. Ryan, J. Mater. Chem. 21, 2601 (2011).

    Article  CAS  Google Scholar 

  41. W. Kasprzyk, P. Krzywda, S. Bednarz, and D. Bogdal, RSC Adv. 5, 90473 (2015).

    Article  CAS  Google Scholar 

  42. J. Chen, L. Song, Y. Wu, B. Zhao, and J. Deng, ACS Appl. Polym. Mater. 4, 4264 (2022).

    Article  CAS  Google Scholar 

  43. A. A. Pakhomov, Yu. N. Kononevich, M. V. Stukalova, E. A. Svidchenko, N. M. Surin, G. V. Cherkaev, O. I. Shchegolikhina, V. I. Martynov, and A. M. Muzafarov, Tetrahedron Lett. 57, 979 (2016).

    Article  CAS  Google Scholar 

  44. A. A. Pakhomov, V. B. Mironiuk, Yu. N. Kononevich, A. A. Korlyukov, A. D. Volodin, T. A. Pryakhina, V. I. Martynov, and A. M. Muzafarov, Mendeleev Commun. 27, 363 (2017).

    Article  CAS  Google Scholar 

  45. A. A. Pakhomov, E. E. Kim, Yu. N. Kononevich, D. S. Ionov, M. A. Maksimova, V. B. Khalchenia, E. G. Maksimov, A. A. Anisimov, O. I. Shchegolikhina, V. I. Martynov, and A. M. Muzafarov, Dyes Pigm. 203, 110371 (2022).

  46. A. S. Belova, A. G. Khchoyan, T. M. Il’ina, Yu. N. Kononevich, D. S. Ionov, V. A. Sazhnikov, D. A. Khanin, G. G. Nikiforova, V. G. Vasil’ev, and A. M. Muzafarov, Polymers (Basel) 14, 5075 (2022).

    Article  CAS  PubMed  Google Scholar 

  47. E. E. Kim, Yu. N. Kononevich, Y. S. Dyuzhikova, D. S. Ionov, D. A. Khanin, G. G. Nikiforova, O. I. Shchegolikhina, V. G. Vasil’ev, and A. M. Muzafarov, Polymers (Basel) 14, 2554 (2022).

    Article  CAS  PubMed  Google Scholar 

  48. E. E. Kim, Yu. N. Kononevich, A. A. Anisimov, M. I. Buzin, V. G. Vasil’ev, A. A. Korlyukov, D. S. Ionov, D. A. Khanin, E. V. Shtykova, V. V. Volkov, and A. M. Muzafarov, React. Funct. Polym. 164, 104896 (2021).

  49. D. F. Eaton, Pure Appl. Chem. 62, 1631 (1990).

    Article  CAS  Google Scholar 

  50. X. Sun, X. Wang, X. Li, J. Ge, Q. Zhang, J. Jiang, and G. Zhang, Macromol. Rapid Commun. 36, 298 (2015).

    Article  CAS  PubMed  Google Scholar 

  51. E. V. Fedorenko, M. K. Behra, and N Kanwishera, J. Fluoresc. 26, 1839 (2016).

    Article  CAS  PubMed  Google Scholar 

  52. A. A. Khrebtov, E. V. Fedorenko, and A. G. Mirochnik, Polymer (Guildf) 256, 125255 (2022).

Download references

Funding

This work was supported by the Russian Science Foundation (project no. 18-73-10152). Characterization of compounds by NMR spectroscopy, TGA, and DSC performed using equipment of the Center for Molecule Composition Studies at the Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences was supported by the Ministry of Science and Higher Education of the Russian Federation (contract no. 075-03-2023-642). Luminescence lifetimes were measured using equipment of the Center for Collective Use “Structural Diagnostics of Materials” within the framework of State Assignment for the Federal National Research Center “Crystallography and Photonics,” Russian Academy of Sciences.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Yu. N. Kononevich.

Ethics declarations

The authors declare that they have no conflicts of interest.

Additional information

Translated by T. Soboleva

Publisher’s Note.

Pleiades Publishing remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kim, E.E., Il’ina, T.M., Kononevich, Y.N. et al. New Fluorescent Materials Based on Polysiloxanes and Boron Bis(β-diketonates). Polym. Sci. Ser. C 65, 267–276 (2023). https://doi.org/10.1134/S1811238223700376

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1811238223700376

Navigation