Abstract
The photophysical processes and photochemical reactions of a 15-crown-5-containing pyridine-based styryl dye and its complexes with potassium, barium, lead, and calcium perchlorates in MeCN were studied by absorption, luminescence, and laser kinetic spectroscopy. The processes of trans—cis-photoisomerization, intersystem crossing to the triplet state, and charge transfer giving the TICT state were found. Quantum chemical calculations for the structures of the dye and its complexes with metal cations were performed. It was concluded that the trans—cis-photoisomerization could proceed through the triplet state with the intermediate formation of a biradical. According to the calculations, the dye complexes with metal cations have 1:1 stoichiometry. In the case of barium cation, the possibility of formation of a 2:1 sandwich complex was also confirmed.
References
S. P. Gromov, Russ. Chem. Bull., 2008, 57, 1325; DOI: https://doi.org/10.1007/s11172-008-0174-9.
S. P. Gromov, A. I. Vedernikov, N. A. Lobova, L. G. Kuz’mina, S. S. Basok, Y. A. Strelenko, M. V. Alfimov, J. A. K. Howard, New J. Chem., 2011, 35, 724.
L. G. Kuz’mina, A. I. Vedernikov, N. A. Lobova, A. V. Churakov, J. A. K. Howard, M. V. Alfimov, S. P. Gromov, New J. Chem., 2007, 31, 980.
S. P. Gromov, O. A. Fedorova, E. N. Ushakov, S. P. Stanislavski, M. V. Alfimov, Dokl. Akad. Nauk SSSR, 1991, 321, 104.
L. S. Atabekyan, V. G. Avakyan, A. K. Chibisov, S. P. Gromov, S. Z. Vatsadze, V. N. Nuriev, A. V. Medved’ko, High Energy Chem., 2019, 53, 115.
L. S. Atabekyan, N. A. Aleksandrova, A. I. Vedernikov, N. A. Lobova, S. P. Gromov, A. K. Chibisov, High Energy Chem., 2017, 51, 189.
L. S. Atabekyan, N. A. Lobova, A. I. Vedernikov, V. G. Avakyan, S. P. Gromov, A. K. Chibisov, Russ. Chem. Bull., 2017, 66, 47; DOI: https://doi.org/10.1007/s11172-017-1698-7.
E. N. Ushakov, M. V. Alfimov, S. P. Gromov, Russ. Chem. Rev. (Int. Ed.), 2008, 77, 39; DOI: https://doi.org/10.1070/RC2008v077n01ABEHOO3757.
E. N. Ushakov, S. P. Gromov, Russ. Chem. Rev., 2015, 84, 787; DOI: https://doi.org/10.1070/RCR4514.
L. S. Atabekyan, N. A. Aleksandrova, S. P. Gromov, Russ. Chem. Bull., 2021, 70, 350; DOI: https://doi.org/10.1007/s11172-021-3092-8.
N. Yu. Sadovskaya, V. N. Glushko, L. I. Blokhina, S. K. Belus’, V. M. Retivov, M. Yu. Zhila, T. A. Cherdynceva, Russ. Chem. Bull., 2022, 71, 1300; DOI: https://doi.org/10.1007/s11172-022-3534-y.
P. A. Panchenko, A. S. Polyakova, Yu. V. Fedorov, O. A. Fedorova, Russ. Chem. Bull., 2021, 70, 1939; DOI: https://doi.org/10.1007/s11172-021-3300-6.
A. I. Vedernikov, S. P. Gromov, N. A. Lobova, L. G. Kuz’mina, Yu. A. Strelenko, J. A. K. Howard, M. V. Alfimov, Russ. Chem. Bull., 2005, 54, 1954; DOI: https://doi.org/10.1007/s11172-006-0064-y.
L. S. Atabekyan, A. K. Chibisov, High Energy Chem., 2007, 41, 91.
M. Montalti, A. Kpedi, L. Prodi, M. T. Gandolfi, Handbook Phochem., London, Taylor and Fransis, 2006, 574.
P. Gans, A. Sabatini, A. Vacca, Talanta, 1996, 43, 1739.
J. P. Perdew, K. Burke, M. Ernzerhof, Phys. Rev. Lett., 1996, 77, 3865.
F. Neese, Comput. Mol. Sci, 2012, 2, 73.
A. Schaefer, H. Horn, R. J. Ahlrichs, Chem. Phys., 1992, 97, 2571.
A. V. Marenich, C. J. Cramer, D. G. Truhlar, J. Phys. Chem. B, 2009, 113, 6378.
D. N. Laikov, Yu. A. Ustynyuk, Russ. Chem. Bull., 2005, 54, 820; DOI: https://doi.org/10.1007/s11172-005-0329-x.
R. D. Shannon, Acta Cryst., 1976, 32, 751.
M. V. Rusalov, B. M. Uzhinov, M. V. Alfimov, S. P. Gromov, Russ. Chem. Bull., 2010, 59, 1207; DOI: https://doi.org/10.1007/s11172-010-0223-z.
Z. R. Grabowski, K. Rotkiewicz, A. Siemiarczuk, J. Luminescence. 1979, 18/19, 420.
W. Rettig, Angew. Chem. Int. Ed. Engl., 1986, 25, 971.
M. V. Rusalov, B. M. Uzhinov, M. V. Alfimov, S. P. Gromov, Russ. Chem. Rev., 2010, 79, 1099; DOI: https://doi.org/10.1070/RC2010v079n12ABEH004170.
B. Carlotti, G. Consiglio, F. Elisei, C. G. Fortuna, U. Mazzucato, A. Spalletti, J. Phys. Chem. A, 2014, 118, 3580.
H. D. M. Sriyarathne, K. R. S. Thenna-Hewa, T. Scott, A. D. Gudmundsdottir, Aust. J. Chem., 2015, 68, 1707.
O. N. Kalugin, V. N. Agienko, N. A. Otroshko, J. Molec. Liquids, 2012, 165, 78.
P. Eberspächer, E. Wismeth, R. Buchner, J. Barthel, J. Molec. Liquids, 2006, 129, 3.
M. D’Arpano, M. Salomon, V. Mauro, J. Solut. Chem., 1995, 24, 685.
L. S. Atabekyan, V. G. Avakyan, A. K. Chibisov, S. P. Gromov, S. Z. Vatsadze, V. N. Nuriev, A. V. Medved’ko, Russ. Chem. Bull., 2019, 88, 2053; DOI: https://doi.org/10.1007/s11172-019-2666-1.
L. G. Kuz’mina, A. V. Churakov, J. A. K. Howard, O. A. Fedorova, S. P. Gromov, M. V. Alfimov, Crystallography Reports, 2003, 48, 613.
Author information
Authors and Affiliations
Corresponding author
Additional information
Dedicated to Academician of the Russian Academy of Sciences I. P. Beletskaya on the occasion of her anniversary.
This study was financially supported by the Russian Science Foundation (Project No. 22-13-00064, as it pertains to the synthesis and absorption and luminescence measurements for styryl dyes) and by the Ministry of Science and Higher Education within the framework of the state assignment for the Federal Scientific Research Center, Crystallography and Photonics, Russian Academy of Sciences (as it pertains to the laser pulse photolysis studies and quantum mechanical calculations).
The authors are grateful to E. N. Ushakov for his valuable comments while reading the manuscript.
No human or animal subjects were used in this research.
The authors declare no competing interests.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 4, pp. 877–894, April, 2023.
Rights and permissions
About this article
Cite this article
Atabekyan, L.S., Avakyan, V.G., Alexandrova, N.A. et al. Molecular photonics of a 15-crown-5-containing styryl dye and its complexes with metal cations. Russ Chem Bull 72, 877–894 (2023). https://doi.org/10.1007/s11172-023-3851-6
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-023-3851-6