Synthesis and Functionalization of Unsymmetrical Terbium(III) Bis-Phthalocyaninates, Promising Components of Hybrid Magnetic Materials

Cover Page

Cite item

Full Text

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

Abstract

A new unsymmetrical terbium bis-Phthalocyaninate Tb(A7B) with one terminal aliphatic OH group was obtained by template cross-condensation of diethoxyphthalonitrile (A) and phthalonitrile (B) functionalized with diethylene glycol moiety. The subsequent functionalization of the complex included the successive replacement of this OH group by the iodide and thioacetate substituents. The synthesized complexes can act as components of hybrid materials upon immobilization on surfaces of various nature.

About the authors

A. V. Yagodin

Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences

Email: martynov@phyche.ac.ru
119071, Moscow, Russia

I. D. Kormshchikov

Faculty of Chemistry, Moscow State University

Email: martynov@phyche.ac.ru
119991, Moscow, Russia

A. G. Martynov

Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences

Email: martynov@phyche.ac.ru
119071, Moscow, Russia

Yu. G. Gorbunova

Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences; Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences

Email: martynov@phyche.ac.ru
119071, Moscow, Russia; 119991, Moscow, Russia

A. Yu. Tsivadze

Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences; Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences

Author for correspondence.
Email: martynov@phyche.ac.ru
119991, Moscow, Russia; 119991, Moscow, Russia

References

  1. Coronado E. // Nat. Rev. Mater. 2019. V. 5. № 2. P. 87. https://doi.org/10.1038/s41578-019-0146-8
  2. Yamashita M. // Bull. Chem. Soc. Jpn. 2021. V. 94. № 1. P. 209. https://doi.org/10.1246/bcsj.20200257
  3. Wang H., Wang B.W., Bian Y. et al. // Coord. Chem. Rev. 2016. V. 306. № P1. P. 195. https://doi.org/10.1016/j.ccr.2015.07.004
  4. Martynov A.G., Horii Y., Katoh K. et al. // Chem. Soc. Rev. 2022. V. 51. № 22. P. 9262. https://doi.org/10.1039/d2cs00559j
  5. Basova T.V., Ray A.K. // ECS J. Solid State Sci. Technol. 2020. V. 9. № 6. P. 061001. https://doi.org/10.1149/2162-8777/ab9fe8
  6. Koifman O.I., Ageeva T.A., Beletskaya I.P. et al. // Macroheterocycles 2020. V. 13. № 4. P. 311. https://doi.org/10.6060/mhc200814k
  7. Chan W.L., Xie C., Lo W.S. et al. // Chem. Soc. Rev. 2021. V. 50. № 21. P. 12189. https://doi.org/10.1039/c9cs00828d
  8. Bouvet M., Gaudillat P., Suisse J.-M.M. // J. Porphyr. Phthalocyanines 2013. V. 17. № 08n09. P. 628. https://doi.org/10.1142/S1088424613300048
  9. Tanaka D., Inose T., Tanaka H. et al. // Chem. Commun. 2012. V. 48. № 63. P. 7796. https://doi.org/10.1039/c2cc00086e
  10. Gonidec M., Davies E.S., McMaster J. et al. // J. Am. Chem. Soc. 2010. V. 132. № 6. P. 1756. https://doi.org/10.1021/ja9095895
  11. Konarev D.V., Khasanov S.S., Batov M.S. et al. // Inorg. Chem. 2019. V. 58. № 8. P. 5058. https://doi.org/10.1021/acs.inorgchem.9b00131
  12. Horii Y., Kishiue S., Damjanović M. et al. // Chem. – A Eur. J. 2018. V. 24. № 17. P. 4320. https://doi.org/10.1002/chem.201705378
  13. Katoh K., Yasuda N., Damjanović M. et al. // Chem. – A Eur. J. 2020. V. 26. № 21. P. 4805. https://doi.org/10.1002/chem.201905400
  14. Stepanow S., Honolka J., Gambardella P. et al. // J. Am. Chem. Soc. 2010. V. 132. № 34. P. 11900. https://doi.org/10.1021/ja105124r
  15. Zhang Y., Wang Y., Liao P. et al. // ACS Nano 2018. V. 12. № 3. P. 2991. https://doi.org/10.1021/acsnano.8b00751
  16. Malavolti L., Poggini L., Margheriti L. et al. // Chem. Commun. 2013. V. 49. № 98. P. 11506. https://doi.org/10.1039/c3cc46868b
  17. Urdampilleta M., Nguyen N.V., Cleuziou J.P. et al. // Int. J. Mol. Sci. 2011. V. 12. № 10. P. 6656. https://doi.org/10.3390/ijms12106656
  18. Gómez-Segura J., Díez-Pérez I., Ishikawa N. et al. // Chem. Commun. 2006. № 27. P. 2866. https://doi.org/10.1039/B606276H
  19. Katoh K., Sato J., Nakanishi R. et al. // J. Mater. Chem. C 2021. V. 9. № 33. P. 10697. https://doi.org/10.1039/D1TC01026C
  20. Schweikart K.-H., Malinovskii V.L., Diers J.R. et al. // J. Mater. Chem. 2002. V. 12. № 4. P. 808. https://doi.org/10.1039/b108520d
  21. Britton J., Martynov A.G., Oluwole D.O. et al. // J. Porphyr. Phthalocyanines 2016. V. 20. P. 1296. https://doi.org/10.1142/S1088424616501042
  22. Oluwole D.O., Yagodin A.V., Britton J. et al. // Dalton Trans. 2017. V. 46. № 46. P. 16190. https://doi.org/10.1039/C7DT03867D
  23. Managa M., Khene S., Britton J. et al. // J. Porphyr. Phthalocyanines 2018. V. 22. № 01n03. P. 137. https://doi.org/10.1142/S1088424618500128
  24. Oluwole D.O., Yagodin A.V., Mkhize N.C. et al. // Chem. Eur. J. 2017. V. 23. № 12. P. 2820. https://doi.org/10.1002/chem.201604401
  25. Iqbal Z., Lyubimtsev A., Hanack M. // Synlett 2008. № 15. P. 2287. https://doi.org/10.1055/s-2008-1078269
  26. Martynov A.G., Birin K.P., Gorbunova Y.G. et al. // Macroheterocycles 2013. V. 6. № 1. P. 23. https://doi.org/10.6060/mhc130221m
  27. Takamatsu S., Ishikawa T., Koshihara S. et al. // Inorg. Chem. 2007. V. 46. № 18. P. 7250. https://doi.org/10.1021/ic700954t
  28. Platonova Y.B., Volov A.N., Tomilova L.G. // J. Catal. 2019. V. 373. P. 222. https://doi.org/10.1016/j.jcat.2019.04.003
  29. Alpugan S., İşci Ü., Albrieux F. et al. // Chem. Commun. 2014. V. 50. № 56. P. 7466. https://doi.org/10.1039/c4cc02523g
  30. Shokurov A.V., Yagodin A.V., Martynov A.G. et al. // ECS J. Solid State Sci. Technol. 2020. V. 9. № 5. P. 051006. https://doi.org/10.1149/2162-8777/ab9a5e
  31. Shokurov A.V., Yagodin A.V., Martynov A.G. et al. // Small 2022. V. 18. № 2. P. 2104306. https://doi.org/10.1002/smll.202104306
  32. May A., Majumdar P., Martynov A.G. et al. // J. Porphyr. Phthalocyanines 2020. V. 24. № 04. P. 589. https://doi.org/10.1142/S108842462050011X
  33. Gorbunova Y.G., Martynov A.G., Birin K.P. et al. // Russ. J. Inorg. Chem. 2021. V. 66. № 2. P. 202. https://doi.org/10.1134/S0036023621020091
  34. Mukherjee D., Manjunatha R., Sampath S. et al. // Phthalocyanines as Sensitive Materials for Chemical Sensors, in: Mater. Chem. Sens., Springer International Publishing, Cham, 2017: pp. 165–226 https://doi.org/10.1007/978-3-319-47835-7_8
  35. Zhang Y., Cai X., Bian Y. et al. // Organic Semiconductors of Phthalocyanine Compounds for Field Effect Transistors (FETs), in: J. Jiang (Ed.), Funct. Phthalocyanine Mol. Mater., Springer Berlin Heidelberg, Berlin, Heidelberg, 2010: pp. 275–322 https://doi.org/10.1007/978-3-642-04752-7
  36. Kumar A., Meunier-Prest R., Bouvet M. // Sensors. 2020. V. 20. № 17. P. 4700. https://doi.org/10.3390/s20174700

Supplementary files

Supplementary Files
Action
1. JATS XML
Download
2.

Download (48KB)
Indexing metadata
3.

Download (57KB)
Indexing metadata
4.

Download (179KB)
Indexing metadata
5.

Download (160KB)
Indexing metadata
6.

Download (89KB)
Indexing metadata

Copyright (c) 2023 А.В. Ягодин, И.Д. Кормщиков, А.Г. Мартынов, Ю.Г. Горбунова, А.Ю. Цивадзе