Synthesis of hybrid molecules based on conjugated polycyclic hydrocarbons and С60 fullerene: application of thin films based on them in organic electronics

Cover Page

Cite item

Full Text

Open Access Open Access
Restricted Access Access granted
Restricted Access Subscription Access

Abstract

Hybrid molecules based on C60 fullerene and strained polycyclic hydrocarbons were synthesized for the first time using the Bingel-Hirsch reaction. Thin films based on the synthesized hybrid compounds were obtained, and the surface morphology of these films was studied. Based on thin films of С60 fullerene adducts containing fragments of conjugated polycyclic hydrocarbons, organic field-effect transistors were fabricated. The current-voltage characteristics of transistors were measured and the mobility of charge carriers was calculated.

About the authors

A. R. Akhmetov

Institute of Petrochemistry and Catalysis, Ufa Federal Research Center of the Russian Academy of Sciences

Email: ahmetov_arslan@mail.ru

R. I. Aminov

Institute of Petrochemistry and Catalysis, Ufa Federal Research Center of the Russian Academy of Sciences

I. N. Mullagaliev

Ufa University of Science and Technology

R. B. Salikhov

Ufa University of Science and Technology

References

  1. Tuktarov A.R., Salikhov R.B., Khuzin A.A., Popod'ko N.R., Safargalin I.N., Mullagaliev I.N., Dzhemilev U.M. // RSC Adv. 2019. Vol. 9. P. 7505. doi: 10.1039/C9RA00939F
  2. Robin M., Harnois M., Molard Y., Jacques E. // Org. Electr. 2016. Vol. 39. P. 214. doi: 10.1016/j.orgel.2016.10.004
  3. Zhou K., Dong H., Zhang H.L., Hu W. // Phys. Chem. Chem. Phys. 2014. Vol. 16. P. 22448. doi: 10.1039/C4CP01700E
  4. Wang C., Dong H., Hu W., Liu Y., Zhu D. // Chem. Rev. 2012. Vol. 112. P. 2208. doi: 10.1021/cr100380z
  5. Sadretdinova Z.R., Akhmetov A.R., Salikhov R.B., Mullagaliev I.N., Salikhov T.R. // Mend. Comm. 2023. Vol. 33. P. 320. doi: 10.1016/j.mencom.2023.04.007
  6. Chen L.-M., Hong Z., Li G., Yang Y. // Adv. Mater. 2009. Vol. 21. P. 1434. doi: 10.1002/adma.200802854
  7. Brabec C.J., Gowrisanker S., Halls I.I.M., Laird D., Jia S., Williams S.P. // Adv. Mater. 2010. Vol. 22. P. 3839. doi: 10.1002/adma.200903697
  8. Nelson J. // Mater. Today. 2011. Vol. 14. P. 462. doi: 10.1016/S1369-7021(11)70210-3
  9. Dang M.T., Hirsch L., Wantz G. // Adv. Mater. 2011. Vol. 23. P. 3597. doi: 10.1002/adma.201100792
  10. Han S.H., Kim G.M., Oh S.Y. // J. Nanosci. Nanotech. 2015. Vol. 15. P. 5446. doi: 10.1166/jnn.2015.10371
  11. Брень В.А., Дубоносов А.Д., Минкин В.И., Черноиванов В.А. // Усп. хим. 1991. Т. 60. С. 913
  12. Bren' V.A., Dubonosov A.D., Minkin V.I., Chernoivanov V.A. // Russ. Chem. Rev. 1991. Vol. 60. P. 451. doi: 10.1070/RC1991v060n05ABEH001088
  13. Дубоносов А.Д., Брень В.А., Черноиванов В.А. // Усп. хим. 2002. Т. 71. С. 1040
  14. Dubonosov A.D., Bren V.A., Chernoivanov V.A. // Russ. Chem. Rev. 2002. Vol. 71. P. 917. doi: 10.1070/RC2002v071n11ABEH000745
  15. Lorenz P., Hirsch A. // Chem. Eur. J. 2020. Vol. 26. P. 5220. doi: 10.1002/chem.201904679
  16. Bonfantini E.E., Officer D.L. // J. Chem. Soc. Chem Commun. 1994. P. 1445. doi: 10.1039/C39940001445
  17. Laine P., Marvaud V., Gourdon A., Launay J.-P., Argazzi R., Bignozzi C.-A. // Inorg. Chem. 1996. Vol. 35. P. 711. doi: 10.1021/ic9507225
  18. Fraysse S., Coudret C., Launay J.-P. // Eur. J. Inorg. Chem. 2000. P. 1581. doi: 10.1002/10990682(200007)2000:7<1581::AIDEJIC1581>3.0.CO;2-2
  19. Morino S., Watanabe T., Magaya Y., Yamashita T., Horie K., Nishikubo T. // J. Photopolym. Sci. Technol. 1994. Vol. 7. P. 121. doi: 10.2494/photopolymer.7.121
  20. Takahashi S., Samata K., Muta H., Machida S., Horie K. // Appl. Phys. Lett. 2001. Vol. 78. P. 13. doi: 10.1063/1.1336164
  21. Herges R., Reif W. // Lieb. Ann. Chem. 1996. P. 761. doi: 10.1002/jlac.199619960519
  22. Starck F., Jones P.G., Herges R. // Eur. J. Org. Chem. 1998. P. 2533. doi: 10.1002/(SICI)10990690(199811)1998:11<2533::AIDEJOC2533>3.0.CO;2-Q
  23. Harada Y., Hatakeyama J., Kawai Y., Sasago M., Endo M., Kishimura S., Maeda K., Ootani M., Komoriya H. Pat. US 6.824.955.2004.
  24. Myers H.K., Schneider A., Suld G. Pat. US 4207080 (1980).
  25. Dzhemilev U.M., Khusnutdinov R.I., Aminov R.I., Tomilov Yu.V., Nefedov O.M., Kurbatov V.E., Vinogradova M.E., Tupakhina E.A. Pat. RU 2640204C2.2017.
  26. Schrauzer G.N. // Tetrahedron Lett. 1970. P. 543. doi: 10.1016/S0040-4039(01)97764-0
  27. Bingel C. // Chem. Ber. 1993. Vol. 126. P. 1957. doi: 10.1002/cber.19931260829
  28. Camps X., Hirsch A. // J. Chem. Soc. Perkin Trans. 1. 1997. P. 1595. doi: 10.1039/A702055D
  29. Hirsch A., Vostrowsky O. // Eur. J. Org. Chem. 2001. Vol. 5. P. 829. doi: 10.1002/10990690(200103)2001:5<829::AID-EJOC829>3.0.CO;2-V
  30. Yan W., Seifermann S.M., Pierrat P., Bräse S. // Org. Biomol. Chem. 2015. Vol. 13. P. 25. doi: 10.1039/C4OB01663G
  31. Palacios-Corella M., Ramos-Soriano J., Souto M., Ananias D., Calbo J., Ortí E., Illescas B.M., Clemente-León M., Martín N., Coronado E. // Chem. Sci. 2021. Vol. 12. P. 757. doi: 10.1039/D0SC05875K
  32. Xing Z., Li S.-H., Hui Y., Wu B.-S., Chen Z.-C., Yun D.-Q., Deng L.-L., Zhang M.-L., Mao B.-W., Xie S.-Y., Huang R.-B., Zheng L.-S. // Nano Energy. 2020. Vol. 74. P. 104859. doi: 10.1016/j.nanoen.2020.104859
  33. Аминов Р.И., Каримова И.М., Хуснутдинов Р.И. // ЖОрХ. 2020. Т. 56. С. 1431
  34. Aminov R.I., Karimova I.M., Khusnutdinov R.I. // Russ. J. Org. Chem. 2020. Vol. 56. P. 1595. doi: 10.1134/S1070428020090158
  35. Lin M.-C., Yeh S.-J., Chen I-R., Lin G. // Protein J. 2011. Vol. 30. P. 220. doi: 10.1007/s10930-011-9323-3
  36. Khusnutdinov R.I., Egorova T.M., Khalilov L.M., Meshcheriakova E.S., Dzhemilev U.M. // Synthesis. 2018. Vol. 50. P. 1555. doi: 10.1055/s-0036-1591881
  37. Hollowood F.S., McKervey M.A., Hamilton R., Rooney J.J. // J. Org. Chem. 1980. Vol. 45. P. 4954. doi: 10.1021/jo01312a026
  38. Хуснутдинов Р.И., Муслимов З.С., Джемилев У.М., Нефедов О.М. // Изв. АН. Сер. xим. 1993. Т. 4. С. 728
  39. Khusnutdinov R.I., Muslimov Z.S., Dzhemilev U.M., Nefedov O.M. // Russ. Chem. Bull. 1993. Vol. 42. P. 692. doi: 10.1007/BF00704004
  40. Джемилев У.М., Ахметов А.Р., Хузин А.А., Дьяконов В.А., Джемилева Л.У., Юнусбаева М.М., Халилов Л.М., Туктаров А.Р. // Изв. АН. Сер. xим. 2019. Т. 5. С. 1036
  41. Dzhemilev U.M., Akhmetov A.R., Khuzin A.A., D'yakonov V.A., Dzhemileva L.U., Yunusbaeva M.M., Khalilov L.M., Tuktarov A.R. // Russ. Chem. Bull. 2019. Vol.68. P. 1036. doi: 10.1007/s11172-019-2516-1
  42. Salikhov R.B., Zilberg R.A., Mullagaliev I.N., Salikhov T.R., Teres Y.B. // Mendeleev Commun. 2022. Vol.32. P. 520. doi 10.1016/j. mencom.2022.07.029
  43. Tuktarov A.R., Salikhov R.B., Khuzin A.A., Safargalin I.N., Mullagaliev I.N., Venidiktova O.V., Valova T.M., Barachevsky V.A., Dzhemilev U.M. // Mendeleev Commun. 2019. Vol. 29. P. 160. doi https: //doi.org/10.1016/j.mencom.2019.03.014
  44. Dong J., Sami S., Balazs D.M., Alessandri R., Jahan, F., Qiu L., Marrink S.J., Havenith R.W.A., Hummelen J.C., Loi M.A., Portale G. // J. Mater. Chem. 2021. Vol. 100. P. 16217. doi: 10.1039/D1TC02753K
  45. Xing Z., Li S.-H., Hui Y., Wu B-S., Chen Z.-C., Yun D.-Q., Deng L.-L., Zhang M.-L., Mao B.-W., Xie S.-Y., Huang R.-B., Zheng L.-S. // Nano Energy. 2020. Vol. 74. P. 104859. doi: 10.1016/j.nanoen.2020.104859

Supplementary files

Supplementary Files
Action
1. JATS XML
Download

Copyright (c) 2023 Russian Academy of Sciences