One-Step Synthesis of Monosilicon-Substituted Norbornenes with Siloxane and Aryl Fragments and Their Polymerization

M. A. Guseva; Гусева М. А.; P. P. Lezhnin; Лежнин П. П.; D. A. Alentiev; Алентьев Д. А.; K. V. Zaitsev; Зайцев К. В.; M. V. Bermeshev; Бермешев М. В.

doi:10.31857/S230811472370036X

One-Step Synthesis of Monosilicon-Substituted Norbornenes with Siloxane and Aryl Fragments and Their Polymerization

Authors: Guseva M.A.¹, Lezhnin P.P.¹, Alentiev D.A.¹, Zaitsev K.V.¹, Bermeshev M.V.¹
Affiliations:
1. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences
Issue: Vol 65, No 2 (2023)
Pages: 210-219
Section: Articles
URL: https://journals.rcsi.science/2308-1147/article/view/232915
DOI: https://doi.org/10.31857/S230811472370036X
EDN: https://elibrary.ru/HKETWN
ID: 232915

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Abstract
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Abstract

Three monosilicon-substituted norbornene monomers with phenyl and siloxane groups at the silicon atom are synthesized by the one-step hydrosilylation of 2,5-norbornadiene. The proposed method allows the synthesis of monomers with a higher content of polymerization-reactive exo-isomer in products compared with similar adducts formed by the Diels‒Аlder reaction. The synthesized monomers show high reactivity in both metathesis polymerization and addition polymerization more sensitive to the substituent volume. Using these monomers two series of high molecular weight silicon-substituted polynorbornenes are prepared which are found to be glassy and thermally stable polymers.

References

Abakumov G.A., Piskunov A.V., Cherkasov V.K., Fedushkin I.L., Ananikov V.P., Eremin D.B., Gordeev E.G., Beletskaya I.P., Averin A.D., Bochkarev M.N., Trifonov A.A., Dzhemilev U.M., D’yakonov V.A., Egorov M.P., Vereshchagin A.N., Syroeshkin M.A., Jouikov V.V., Muza-farov A.M., Anisimov A.A., Arzumanyan A.V., Konone-vich Yu.N., Temnikov M.N., Sinyashin O.G., Budnikova Yu.H., Burilov A.R., Karasik A.A., Mironov V.F., Storozhenko P.A., Shcherbakova G.I., Trofimov B.A., Amosova S.V., Gusarova N.K., Potapov V.A., Shur V.B., Burlakov V.V., Bogdanov V.S., Andreev M.V. // Russ. Chem. Rev. 2018. V. 87. № 5. P. 393.
Blanco I. // Polymers. 2021. V. 13. P. 188.
Grushevenko E.A., Borisov I.L., Volkov A.V. // Pet. Chem. 2021. V. 61. № 9. P. 959.
Khotimskii V.S., Filippova V.G., Bryantseva I.S., Bondar V.I., Shantarovich V.P., Yampolskii Yu.P. // J. Appl. Polym. Sci. 2000. V. 78. № 9. P. 1612.
Kalmykov D., Balynin A., Yushkin A., Grushevenko E., Sokolov S., Malakhov A., Volkov A., Bazhenov S. // Membranes. 2022. V. 12. № 11. P. 1160.
Wang X., Wilson T.J., Alentiev D., Gringolts M., Finkelshtein E., Bermeshev M., Long B.K. // Polym. Chem. 2021. V. 12. № 20. P. 2947.
Alentiev D.A., Bermeshev M.V. // Polym. Rev. 2022. V. 62. № 2. P. 400.
Zheng X.H., Zhao J.F., Zhao T.P., Yang T., Ren X.K., Liu C.Y., Yang S., Chen E.Q. // Macromolecules. 2018. V. 51. № 12. P. 4484.
Sundell B.J., Lawrence J.A., Harrigan D.J., Vaughn J.T., Pilyugina T.S., Smith D.R. // RSC Adv. 2016. V. 6. № 57. P. 51619.
Vaughn J.T., Harrigan D.J., Sundell B.J., Lawrence J.A., Yang J. // J. Membr. Sci. 2017. V. 522. P. 68.
Maroon C.R., Townsend J., Gmernicki K.R., Harrigan D.J., Sundell B.J., Lawrence J.A., Mahurin S.M., Vogiatzis K.D., Long B.K. // Macromolecules. 2019. V. 52. № 4. P. 1589.
Maroon C.R., Townsend J., Higgins M.A., Harrigan D.J., Sundell B.J., Lawrence J.A., O’Brien J.T., O’Neal D., Vogiatzis K.D., Long B.K. // J. Membr. Sci. 2020. V. 595. P. 117532.
Hong T., Niu Z., Hu X., Gmernicki K., Cheng S., Fan F., Johnson J.C., Hong E., Mahurin S., Jiang D.E., Long B., Mays J., Sokolov A., Saito T. // Chem. Sus. Chem. 2015. V. 8. № 21. P. 3595.
Gmernicki K.R., Hong E., Maroon C.R., Mahurin S.M., Sokolov A.P., Saito T., Long B.K. // ACS Macro Lett. 2016. V. 5. № 7. P. 879.
Bermeshev M.V., Syromolotov A.V., Gringolts M.L., Lakhtin V.G., Finkelshtein E.Sh. // Tetrahedron Lett. 2011. V. 52. № 46. P. 6091.
Guseva M.A., Alentiev D.A., Bermesheva E.V., Zamilatskov I.A., Bermeshev M.V. // RSC Adv. 2019. V. 9. № 57. P. 33029.
García-Loma R., Albéniz A.C. // Asian J. Org. Chem. 2019. V. 8. № 3. P. 304.
Suslov D.S., Bykov M.V., Kravchenko O.V. // Polymer Science C. 2019. V. 61. № 1. P. 145.
Sundell B.J., Lawrence J.A., Harrigan D.J., Lin S., Headrick T.P., O’Brien J.T., Penniman W.F., Sandler N. // ACS Macro Lett. 2020. V. 9. № 9. P. 1363.
Guseva M.A., Alentiev D.A., Bakhtin D.S., Borisov I.L., Borisov R.S., Volkov A.V., Finkelshtein E.Sh., Bermeshev M.V. // J. Membr. Sci. 2021. V. 638. P. 119656.
Katsumata T., Shiotsuki M., Sanda F., Masuda T. // Polymer. 2009. V. 50. № 6. P. 1389.
Gringol’ts M.L., Bermeshev M.V., Syromolotov A.V., Starannikova L.E., Filatova M.P., Makovetskii K.L., Finkel’shtein E.Sh. // Pet. Chem. 2010. V. 50. № 5. P. 352.