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Synthesis and evaluation of properties of the optically transparent (co)polyimides based on cyclic and alicyclic diamines and dianhydrides of aromatic tetracarboxylic acids

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Abstract

Optically transparent polyimides (PIs) containing adamantane moieties in the structure of diamine unit were synthesized, and their properties were evaluated. The quantum-chemical calculations were also performed and revealed the energy difference (As) between the HOMO of the diamine and LUMO of the anhydride moieties for a large range of adamantane-containing PIs, which is usually associated with the optical absorption of organic compounds. It was found that the value of As does not always determine the optical properties of PI, especially in the case of PI with dianhydride moieties capable of strong intermolecular interactions. The presence of methyl groups at the core of adamantane-containing diamine leads to amorphization of the polymer, causing a positive effect on the optical properties of PI.

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References

  1. M. K. Ghosh, K. L. Mittal, Polyimides: Fundamental and Applications, Marcel Dekker, New York, 1996, 912.

    Google Scholar 

  2. E. P. Favvas, F. K. Katsaros, S. K. Papageorgiou, A. A. Sapalidis, A. C. Mitropoulos, A. Ch. A Rev. Latest Devel. Polyimide Based Membranes for CO2 Separations, React. Funct. Polym., 2017, 120.

  3. L. F. Thompson, C. G. Wilson, S. Tagawa, Polym. Microelectronics: Resists and Dielectrics, ACS Symposium Series 537, Washington, DC, 1994, p. 214, 571.

  4. A. A. Perichaud, R. M. Iskakov, A. Kurbatov, T. Z. Akhmetov, O. Y. Prokohdko, I. V. Razumovskaya, S. L. Bazhenov, P. Y. Apel, V. Yu. Voytekunas, M. J. Abadie, M. Auto-repar. Polyim. Film Coatings for Aerospace Applications Challenges & Perspectives. In High Performance Polymers — Polyimides Based — from Chemistry to Applications, Abadie, InTech, Croatia, 2012, 244.

    Google Scholar 

  5. X.-H. Ma, S.-Y. Yang, Polyimide Gas Separation Membrane. In Advanced Polyimide Materials Synthesis, Characterization and Applications, Elsevier, Amsterdam, 2018, 498, p. 257–322.

    Google Scholar 

  6. D. Lee, Y. W. Lim, H. G. Im, S. Jeong, S. Ji, Y. H. Kim, G. M. Choi, J. U. Park, J. Y. Lee, J. Jin, ACS Appl. Mater. Interfaces, 2017, 9, 24161–24168.

    Article  CAS  Google Scholar 

  7. M. Kim, J. Park, S. Ji, S. H. Shin, S. Y. Kim, Y. C. Kim, J. Y. Kim, J. U. Park, Nanoscale, 2016, 8, 9504–9510.

    Article  CAS  Google Scholar 

  8. R. A. Dine-Hart, W. W. Wright, J. Appl. Polym. Sci., 1967, 11, 609–627.

    Article  CAS  Google Scholar 

  9. T. A. Gordin, B. V. Kotov, O. V. Kolninov, A. N. Pravednikov, Polym. Sci. USSR, 1973, 15, No. 5, 378–381.

    Google Scholar 

  10. V. C. Voishchev, O. V. Kolninov, T. A. Gordina, B. V. Kotov, B. I. Sazhin, B. I. Mikhantyev, A. N. Pravednikov, Polym. Sci. USSR, 1974, B16, No. 4, 295–298.

    Google Scholar 

  11. B. V. Kotov, T. A. Gordina, Z. S. Voishchev, O. V. Kononov, A. N. Pravednikov, Polym. Sci. USSR, 1977, A19, No. 3, 614–618.

    Google Scholar 

  12. B. V. Kotov, Dis. dokt. khim. nauk [Dr. Sci. Thesis Work], L. Ya. Karpov Institute of Physics and Chemistry, Moscow, 1992, p. 66 (in Russian).

    Google Scholar 

  13. B. A. Zhubanov, I. A. Arkhipova, O. A. Almabekov, Novyye termostoykie geterotsiklicheskie polimery [Novel Heat-Resistant Heterocyclic Polymers], Alma-Ata, Nauka, 1979, p. 252 (in Russian).

  14. B. V. Kotov, T. A. Gordina, V. S. Voishchcv, O. V. Kolninov, A. N. Pravednikov, Polym. Sci. USSR, Ser. A, 1977, 614–619, 660.

    Google Scholar 

  15. Shinji Ando, Tohru Matsuura, Shigekuni Sasaki, Polym. J., 1997, 69–76, 1033.

    Google Scholar 

  16. I. A. Novakov, B. S. Orlinson, D. V. Zavyalov, S. V. Mednikov, E. N. Savelyev, E. A. Potapenkova, M. A. Nakhod, A.M. Pichugin, A.V. Kireeva, M. N. Kovaleva, Russ. Chem. Bull., 2021, 70, 1141.

    Article  CAS  Google Scholar 

  17. I. A. Novakov, B. S. Orlinson, Polimery na osnove proizvodnykh adamantana: sintez, svoystva, napravleniya prakticheskogo primeneniya [Polymers Based on Adamantane Derivatives: Synthesis, Properties, and Directions of Practical Application], Volgograd State Technical University, Volgograd, 2005, p. 96 (in Russian).

    Google Scholar 

  18. K.-H. Nam, H. K. Choi, H. Yeo, N.-H. You, B.-C. Ku, Y. Jaesang, Polymers, 2018, 10, № 6, 630.

    Article  Google Scholar 

  19. P. K. Tapaswi, Chang-Sik Ha, Macromolecular Chemistry and Physics, 2019, 220, 1800313.

    Article  Google Scholar 

  20. Y. Ma, C. Hu, H. Guo, L. Fan, S. Yang, H.-W. Sun, Polym. J., 2018, 148, 356–369.

    Article  CAS  Google Scholar 

  21. S. V. Vinogradova, V. A. Vasnev, Polikondensatsionnyye protsessy i polimery [Polycondensation Processes and Polymers], 2000, 373 (in Russian).

  22. Khimicheskaya entsiklopediya [Chemical Encyclopedia] in 5 volumes, Vol. 2, Ed. I. L. Knunyats, Sovetskaya entsiklopediya, Moscow, 1990 (in Russian).

  23. A. A. Gayle, G. D. Zalishchevskiy, N-Metilpirrolidon: polucheniye, svoystva i primeneniye v kachestve selektivnogo rastvoritelya [N-Methylpyrrolidone: Preparation, Properties and Application as a Selective Solvent], Khimiya, Sankt-Peterburg, 2005, p. 705 (in Russian).

    Google Scholar 

  24. A. Rieche, W. Schön, Chem. Ber., 1966, 99, 3238–3243.

    Article  CAS  Google Scholar 

  25. I. A. Novakov, B. S. Orlinson, D. V. Zavyalov, V. I. Porkhun, E. N. Savelyev, E. A. Potapenkova, O. V. Vostrikova, M. A. Nakhod, A.V. Kireeva, A. M. Pichugin, Russ. Chem. Bull., 2020, 69, 1096–1101.

    Article  CAS  Google Scholar 

  26. I. A. Novakov, B. S. Orlinson, V. I. Porkhun, O. V. Vostrikova, E. N. Saveliev, E. A. Potaenkova, M. A. Nakhod, A. M. Pichugin, A. V. Kireeva, Izv. Volg. GTU, Ser. Khimia i tekhnologia elemento-organicheskikh monomerov i polimernykh materialov [Proc. Volg. STU. Chemistry and Technology of Organoelement Monomers and Polymeric Materials], 2018, 154, 59–6 (in Russian).

    Google Scholar 

  27. I. A. Novakov, B. S. Orlinson, N. N. Mamutova, E. N. Savelyev, E. A. Potayenkova, L. A. Pyntya, M. A. Nakhod, Russ. J. Gen. Chem., 2016, 86, 924–928.

    Article  Google Scholar 

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Authors and Affiliations

  1. Volgograd State Technical University, 28 prosp. im. Lenina, 400005, Volgograd, Russian Federation

    I. A. Novakov, B. S. Orlinson, D. V. Zavyalov, A. I. Bogdanov, E. N. Savelyev, E. A. Potayenkova, M. A. Nakhod, A. M. Pichugin, A. G. Polikarpova, M. N. Kovaleva & P. E. Antonova

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  1. I. A. Novakov
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  2. B. S. Orlinson
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  3. D. V. Zavyalov
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  4. A. I. Bogdanov
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  5. E. N. Savelyev
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  6. E. A. Potayenkova
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  7. M. A. Nakhod
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  8. A. M. Pichugin
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  9. A. G. Polikarpova
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  10. M. N. Kovaleva
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  11. P. E. Antonova
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Corresponding author

Correspondence to E. A. Potayenkova.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 750–759, April, 2022.

This work was financially supported by the Russian Foundation for Basic Research (Project No. 19-33-90119-19).

Some experiments were performed using the equipment of the Center for Collective Use “Physical and Chemical Research Methods” at the Volgograd State Technical University.

No human or animal subjects were used in this research.

The authors declare no competing interests.

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Novakov, I.A., Orlinson, B.S., Zavyalov, D.V. et al. Synthesis and evaluation of properties of the optically transparent (co)polyimides based on cyclic and alicyclic diamines and dianhydrides of aromatic tetracarboxylic acids. Russ Chem Bull 71, 750–759 (2022). https://doi.org/10.1007/s11172-022-3475-5

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  • DOI: https://doi.org/10.1007/s11172-022-3475-5

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