Abstract—
The results of investigation of the optical and electrochemical properties of substituted phthalimides linked to a cymantrenyl moiety by IR and NMR spectroscopy, UV-Vis spectroscopy, and cyclic voltammetry and also by DFT calculations are presented. It was shown that the optical, donor-acceptor, and redox properties of the organometallic phthalimides are affected by substituents in position 1 of the side chain of the cymantrene Cp and in position 4 of the phthalimide benzene ring. The reactions of dicarbonyl chelates with external ligands in the dark attest to hemilability of the Mn–O=C(imide) bond.
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1134%2FS0036023623601435/MediaObjects/11502_2023_3114_Fig1_HTML.png)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1134%2FS0036023623601435/MediaObjects/11502_2023_3114_Fig2_HTML.png)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1134%2FS0036023623601435/MediaObjects/11502_2023_3114_Fig3_HTML.png)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1134%2FS0036023623601435/MediaObjects/11502_2023_3114_Fig4_HTML.png)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1134%2FS0036023623601435/MediaObjects/11502_2023_3114_Fig5_HTML.png)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1134%2FS0036023623601435/MediaObjects/11502_2023_3114_Fig6_HTML.png)
Similar content being viewed by others
REFERENCES
Jun-ichi Nishida, Yoshiki Morikawa, Akito Hashimoto, et al., Mater. Adv. 2, 7861 (2021). https://doi.org/10.1039/d1ma00716e
Biao Chen, Xuepeng Zhang, Yucai Wang, et al., Chem. Asian J. 14, 751 (2019). https://doi.org/10.1002/asia.201801002
A. Georgiev, D. Yordanov, D. Dimov, et al., J. Photochem. Photobiol., A 393, 112443 (2020). https://doi.org/10.1016/j.jphotochem.2020.112443
N. Venkatramaiah, G. Dinesh Kumar, Y. Chandrasekaran, et al., ACS Appl. Mater. Interfaces 10, 3838 (2018). https://doi.org/10.1021/acsami.7b11025
**aodong He, Lunxiang Yin, and Yanqin Li, New J. Chem. 43, 6577 (2019). https://doi.org/10.1039/C9NJ00600A
Fanyong Yan, Chunhui Yi, Zhonghua Hao, et al., Surf. Colloids, A 650, 129626 (2022). https://doi.org/10.1016/j.colsurfa.2022.129626
M. Zawadzka, P. Nitschke, M. Musiol, et al., Molecules 28, 1740 (2023). https://doi.org/10.3390/molecules28041740
D. Çakal, S. Ertan, A. Cihaner, et al., Dyes Pigm. 161, 411 (2019). https://doi.org/10.1016/j.dyepig.2018.10.002
Wei Lv, Huijiao Liu, Wen Wang et al., RSC Adv. 7, 18384 (2017). https://doi.org/10.1039/C6RA28757C
Zhijun Li, Yong ** Jeong, Jisu Hong, et al., Appl. ACS, Mater. Interfaces 14, 7073 (2022). https://doi.org/10.1021/acsami.1c20278
F. Dierschke, J. Jacob, and K. Mullen, Synth. Met. 156, 433 (2006). https://doi.org/10.1016/j.synthmet.2005.11.016
Quanyou Feng, **aojun Zheng, Hongjian Wang, et al., Mater. Adv. 2, 4000 (2021). https://doi.org/10.1039/d1ma00181g
R. Orita, M. Franckevicius, A. Vysniauskas, et al., Phys. Chem. Chem. Phys. 20, 16033 (2018). https://doi.org/10.1039/c8cp01999a
Taku Shoji, Nanami Iida, Akari Yamazaki, et al., Org. Biomol. Chem. 18, 2274 (2020). https://doi.org/10.1039/d0ob00164c
Yizhen Zhan, Xue Zhao, Wei Wang, et al., Dyes Pigm. 146, 240 (2017). https://doi.org/10.1016/j.dyepig.2017.07.013
D. Singha, D. K. Sahu, K. Sahu, et al., J. Phys. Chem. B 122, 6966 (2018). https://doi.org/10.1021/acs.jpcb.8b03901
A. Tan, E. Bozkurt, Y. Kara, et al., J. Fluoresc. 27, 981 (2017). https://doi.org/10.1007/s10895-017-2033-2
D. Majhi, S. K. Das, P. K. Sahu, et al., Phys. Chem. Chem. Phys. 16, 18349 (2014). https://doi.org/10.1039/c4cp01912a
Yuanyuan Qin, Guo** Li, Ting Qi, et al., Mater. Chem. Front. 4, 1554 (2020). https://doi.org/10.1039/D0QM00084A
E. S. Kelbysheva, T. V. Strelkova, M. G. Ezernitskaya, et al., Chem. Select 8, e202204162 (2023). https://doi.org/10.1002/slct.202204162
E. S. Kelbysheva, L. N. Telegina, E. A. Ershova, et al., Russ. Chem. Bull. 66, 327 (2017). https://doi.org/10.1007/s11172-017-1735-6
P. F. Yang and G. K. Yang, J. Am. Chem. Soc. 114, 6937 (1992). https://doi.org/10.1021/ja00043a061
E. S. Kelbysheva, T. V. Strelkova, M. G. Ezernitskaya, et al., Chem. Select 6, 9861 (2021). https://doi.org/10.1002/slct.202102464
E. S. Kelbysheva, L. N. Telegina, O. V. Abramova, et al., Russ. Chem. Bull. 11, 2646 (2015). https://doi.org/10.1007/s11172-015-1203-0
C. Zhang, Z. Niu, Y. Ding, et al., Chem 4, 2814 (2018). https://doi.org/10.1016/j.chempr.2018.08.024
A. D. Hendsbee, S. M. McAfee, J.-P. Sun, et al., J. Mater. Chem. C 3, 8904 (2015). https://doi.org/10.1039/c5tc01877c
K. Wu, B. Pudasaini, J. Y. Park, et al., Organometallics 3, 679 (2020). https://doi.org/10.1021/acs.organomet.9b00822
A. S. Kostyuchenko, A. Kurowska, P. Zassowski, et al., Org. Chem. 84, 10040 (2019). https://doi.org/10.1021/acs.joc.9b01216
ACKNOWLEDGMENTS
Infrared and NMR spectral studies were carried out using the research equipment of the Center of Molecular Structure Investigation of the Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, supported by the Ministry of Science and Higher Education of the Russian Federation.
Funding
This study was supported by the Russian Science Foundation (RSF no. 23-23-00192).
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare that they have no conflicts of interest.
Additional information
Translated by Z. Svitanko
Supplementary Information
The supplementary information presents experimental data and characterization of the obtained compounds by NMR (Fig. S1–S11), IR (Fig. S12–S16), and CV (Fig. S17–S18) and the results of DFT calculations (Fig. S19–S33, Table S1).
Rights and permissions
About this article
Cite this article
Kelbysheva, E.S., Strelkova, T.V., Ezernitskaya, M.G. et al. Substituted Phthalimides Linked to the Cymantrenyl Moiety: Molecules with Tunable Optical and Electrochemical Properties. Russ. J. Inorg. Chem. 68, 1237–1246 (2023). https://doi.org/10.1134/S0036023623601435
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0036023623601435