Copper(II) Catecholate Complexes with Polypyridyl Ligands

O. Yu. Trofimova; Трофимова О. Ю.; K. I. Pashanova; Пашанова К. И.; I. V. Ershova; Ершова И. В.; M. V. Arseniev; Арсеньев М. В.; I. A. Yakushev; Якушев И. А.; P. V. Dorovatovsky; Дороватовский П. В.; R. R. Aisin; Айсин Р. Р.; A. V. Piskunov; Пискунов А. В.

doi:10.31857/S0044457X23600846

Copper(II) Catecholate Complexes with Polypyridyl Ligands

Authors: Trofimova O.Y.¹, Pashanova K.I.¹, Ershova I.V.¹, Arseniev M.V.¹, Yakushev I.A.², Dorovatovsky P.V.³, Aisin R.R.⁴, Piskunov A.V.¹
Affiliations:
1. Rasuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences
2. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences
3. National Research Center “Kurchatov Institute”
4. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences
Issue: Vol 68, No 9 (2023)
Pages: 1154-1164
Section: КООРДИНАЦИОННЫЕ СОЕДИНЕНИЯ
URL: https://journals.rcsi.science/0044-457X/article/view/136462
DOI: https://doi.org/10.31857/S0044457X23600846
EDN: https://elibrary.ru/YIEZEI
ID: 136462

Cite item

Full Text

Open Access
Restricted Access

Access granted
Restricted Access

Subscription Access

Abstract
About the authors
References
Supplementary files
Statistics

Abstract

Copper(II) catecholate complexes based on 3,6-di-tert-butyl-o-benzoquinone with N-donor ligands of the phenanthroline series have been synthesized: (3,6-Cat)Cu(Phen) (I), (3,6-Cat)Cu(DPQ) (II), and (3,6-Cat)Cu(DPPZ) (III), where 3,6-Cat is the 3,6-di-tert-butyl-o-benzoquinone dianion, Phen is phenanthroline, DPQ is dipyrido[3,2-d:2',3'-f]quinoxaline, and DPPZ is dipyrido[3,2-a:2',3'-c]phenazine. The synthesized copper(II) complexes demonstrate intramolecular ligand-to-ligand charge transfer responsible for their intense violet color. The electronic structure of the synthesized chromophores was studied by electronic spectroscopy, cyclic voltammetry, and quantum-chemical calculations. The molecular and crystal structures of the synthesized compounds were determined by X-ray diffraction analysis (CIF files CCDC 2 250 975 (I⋅THF), 2 250 976 ([(II⋅THF)(II)]⋅3THF), 2250977 (II)).

Keywords

copper, redox-active ligand, catecholate, phenanthroline, charge transfer, electronic, spectroscopy, cyclic voltammetry, single crystal X-ray diffraction

References

Sobottka S., Nößler M., Ostericher A.L. et al. // Chem. Eur. J. 2020. V. 26. P. 1314. https://doi.org/10.1002/chem.201903700
Romashev N.F., Abramov P.A., Bakaev I.V. et al. // Inorg. Chem. 2022. V. 61. P. 2105. https://doi.org/10.1021/acs.inorgchem.1c03314
Shultz D.A., Stephenson R., Kirk M.L. // Dalton Trans. 2023. V. 52. P. 1970. https://doi.org/10.1039/D2DT03385B
Yang J., Kersi D.K., Giles L.J. et al. // Inorg. Chem. 2014. V. 53. P. 4791. https://doi.org/10.1021/ic500217y
Kramer W.W., Cameron L.A., Zarkesh R.A. et al. // Inorg. Chem. 2014. V. 53. P. 8825. https://doi.org/10.1021/ic5017214
Shavaleev N.M., Davies E.S., Adams H. et al. // Inorg. Chem. 2008. V. 47. P. 1532. https://doi.org/10.1021/ic701821d
Benedix R., Hennig H., Kunkely H. et al. // Chem. Phys. Lett. 1990. V. 175. P. 483. https://doi.org/10.1016/0009-2614(90)85568-W
Cameron L.A., Ziller J.W., Heyduk A.F. // Chem. Sci. 2016. V. 7. P. 1807. https://doi.org/10.1039/C5SC02703A
Ghosh P., Begum A., Herebian D. et al. // Angew. Chem. Int. Ed. 2003. V. 42. P. 563. https://doi.org/10.1002/anie.200390162
Best J., Sazanovich I.V., Adams H. et al. // Inorg. Chem. 2010. V. 49. P. 10041. https://doi.org/10.1021/ic101344t
Scattergood P.A., Jesus P., Adams H. et al. // Dalton Trans. 2015. V. 44. P. 11705. https://doi.org/10.1039/C4DT03466J
Yang J., Kersi D.K., Richers C.P. et al. // Inorg. Chem. 2018. V. 57. P. 13470. https://doi.org/10.1021/acs.inorgchem.8b02087
Kirk M.L., Shultz D.A., Marri A.R. et al. // J. Am. Chem. Soc. 2022. V. 144. P. 21005. https://doi.org/10.1021/jacs.2c09680
Kirk M.L., Shultz D.A., Hewitt P. et al. // Chem. Sci. 2021. V. 12. P. 13704. https://doi.org/10.1039/D1SC02965G
Kirk M.L., Shultz D.A., Chen J. et al. // J. Am. Chem. Soc. 2021. V. 143. P. 10519. https://doi.org/10.1021/jacs.1c04149
Hagberg D.P., Yum J.-H., Lee H. et al. // J. Am. Chem. Soc. 2008. V. 130. P. 6259. https://doi.org/10.1021/ja800066y
García-Cañadas J., Meacham A.P., Peter L.M. et al. // Angew. Chem. Int. Ed. 2003. V. 42. P. 3011. https://doi.org/10.1002/anie.200351338
Ward M.D. // J. Solid State Electrochem. 2005. V. 9. P. 778. https://doi.org/10.1007/s10008-005-0668-4
Sekar N., Gehlot V.Y. // Resonance. 2010. V. 15. P. 819. https://doi.org/10.1007/s12045-010-0091-8
Atallah H., Taliaferro C.M., Wells K.A. et al. // Dalton Trans. 2020. V. 49. P. 11565. https://doi.org/10.1039/D0DT01765E
Ершова И.В., Малеева А.В., Айсин Р.Р. и др. // Изв. Академии наук. Сер. хим. 2023. Т. 72. С. 193.
Maleeva A.V., Ershova I.V., Trofimova O.Y. et al. // Mendeleev Commun. 2022. V. 32. P. 83. https://doi.org/10.1016/j.mencom.2022.01.027
Малеева А.В., Трофимова О.Ю., Якушев И.А. и др. // Коорд. химия. 2023. Т. 49 (в печати).
Pashanova K.I., Bitkina V.O., Yakushev I.A. et al. // Molecules. 2021. V. 26. P. 4622. https://doi.org/10.3390/molecules26154622
Pashanova K.I., Ershova I.V., Trofimova O.Y. et al. // Molecules. 2022. V. 27. P. 8175. https://doi.org/10.3390/molecules27238175
Rall J., Wanner M., Albrecht M. et al. // Chem. Eur. J. 1999. V. 5. P. 2802. https://doi.org/10.1002/(SICI)1521-3765(19991001)5:10<2802::AID-CHEM2802>3.0.CO;2-5
Abakumov G.A., Krashilina A.V., Cherkasov V.K. et al. // Russ. Chem. Bull. 2001. V. 50. P. 2193. https://doi.org/10.1023/A:1015022006445
Kaizer J., Zsigmond Z., Ganszky I. et al. // Inorg. Chem. 2007. V. 46. P. 4660. https://doi.org/10.1021/ic062309a
Ovcharenko V.I., Gorelik E.V., Fokin S.V. et al. // J. Am. Chem. Soc. 2007. V. 129. P. 10512. https://doi.org/10.1021/ja072463b
Fursova E.Yu., Ovcharenko V.I., Gorelik E.V. et al. // Russ. Chem. Bull. 2009. V. 58. P. 1139. https://doi.org/10.1007/s11172-009-0148-6
Davidson R.A., Hao J., Rheingold A.L. et al. // Polyhedron. 2017. V. 133. P. 348. https://doi.org/10.1016/j.poly.2017.05.038
Cherkasova A.V., Kozhanov K.A., Zolotukhin A.A. et al. // Russ. J. Coord. Chem. 2019. V. 45. P. 489. https://doi.org/10.1134/S1070328419070029
Kuropatov V.A., Cherkasova A.V., Martyanov K.A. et al. // Eur. J. Inorg. Chem. 2021. V. 2021. P. 3292. https://doi.org/10.1002/ejic.202100517
Buchanan R.M., Wilson-Blumenberg C., Trapp C. et al. // Inorg. Chem. 1986. V. 25. P. 3070. https://doi.org/10.1021/ic00237a029
Verma P., Weir J., Mirica L. et al. // Inorg. Chem. 2011. V. 50. P. 9816. https://doi.org/10.1021/ic200958g
Lakk-Bogáth D., Csonka R., Lorencz N. et al. // Polyhedron. 2015. V. 102. P. 185. https://doi.org/10.1016/j.poly.2015.09.026
van der Tol E.B., van Ramesdonk H.J., Verhoeven J.W. et al. // Chem. Eur. J. 1998. V. 4. P. 2315. https://doi.org/10.1002/(SICI)1521-3765(19981102)4: 11<2315::AID-CHEM2315>3.0.CO;2-E
Abakumov G.A., Cherkasov V.K., Bubnov M.P. et al. // Russ. Chem. Bull. 1992. V. 41. P. 1813. https://doi.org/10.1007/BF00863815
Svetogorov R.D., Dorovatovskii P.V., Lazarenko V.A. // Cryst. Res. Technol. 2020. V. 55. P. 1900184. https://doi.org/10.1002/crat.201900184
Kabsch W. // Acta Crystallogr., Sect. D. 2010. V. 66. P. 125. https://doi.org/10.1107/S0907444909047337
Bruker. APEX3, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. 2016.
Sheldrick G.M. // Acta Crystallogr. 2015. V. A71. P. 3. https://doi.org/10.1107/S2053273314026370
Sheldrick G.M. // Acta Crystallogr. 2015. V. C71. P. 3. https://doi.org/10.1107/S2053229614024218
Dolomanov O.V., Bourhis L.J., Gildea R.J. et al. // J. Appl. Crystallogr. 2009. V. 42. P. 339. https://doi.org/10.1107/S0021889808042726
Frisch M.J., Trucks G.W., Schlegel H.B. et al. // Revision D.01. Gaussian, Inc. Wallingford CT. 2013.
Hathaway B.J., Billing D.E. // Coord. Chem. Rev. 1970. V. 5. P. 143. https://doi.org/10.1016/S0010-8545(00)80135-6
Piskunov A.V., Maleeva A.V., Mescheryakova I.N. et al. // Eur. J. Inorg. Chem. 2012. P. 4318. https://doi.org/10.1002/ejic.201200535
Chegerev M.G., Piskunov A.V., Maleeva A.V. et al. // Eur. J. Inorg. Chem. 2016. P. 3813. https://doi.org/10.1002/ejic.201600501
Davidson R.A., Hao J., Rheingold A.L. et al. // Polyhedron. 2017. V. 136. P. 176. https://doi.org/10.1016/j.poly.2017.10.003
Batsanov S.S. // Russ. J. Inorg. Chem. 1991. V. 36. P. 1694.
Zairov R.R., Yagodin A.V., Khrizanforov M. et al. // J. Nanopart. Res. 2019. V. 21. P. 12.
Райхардт К. Растворители и эффекты среды в органической химии. М.: Мир, 1991. 764 с.