Email this article Spectral and photochemical properties of styrylquinoline–carbazole dyad in neutral and protonated forms
- Authors: Budyka M.F.1, Li V.M.1, Gavrishova T.N.1, Kitina P.V.2, Soulimenkov I.V.3
-
Affiliations:
- Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry
- Faculty of Basic Physicochemical Engineering, Moscow State University
- Branch of Semenov Federal Research Center for Chemical Physics
- Issue: Vol 59, No 2 (2025)
- Pages: 94-103
- Section: ФОТОХИМИЯ
- URL: https://bakhtiniada.ru/0023-1193/article/view/304490
- DOI: https://doi.org/10.31857/S0023119325020041
- EDN: https://elibrary.ru/algjns
- ID: 304490
Cite item
Open Access
Access granted
Subscription Access
Abstract
Spectral-luminescent and photochemical properties of neutral and protonated forms of styrylquinoline – carbazole dyad SQ3Cbz, in which the carbazole fragment (Cbz) is linked to the 2-styrylquinoline (SQ) residue via an oxytrimethylene bridge, were studied. It was shown that in both forms of SQ3Cbz strong quenching of the Cbz fragment fluorescence is observed due to energy transfer to the SQ fragment via the Förster mechanism. In the protonated form of the dyad, where the proton is localized on the SQ fragment, a significant decrease in the quantum yields of trans-cis photoisomerization and fluorescence of the SQ fragment is observed, as well as a blue shift of its emission band compared to the model SQ chromophore. It is suggested that the observed effects are related to the formation of folded dyad conformers in which the SQ chromophore has a more rigid structure and/or the process of electron transfer from Cbz to the protonated SQ fragment. DFT calculations predict the possibility of the formation of folded dyad conformers that are stabilized by π-stacking interactions between Cbz and SQ fragments.
About the authors
M. F. Budyka
Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry
Email: budyka@icp.ac.ru
Chernogolovka, Russia
V. M. Li
Federal Research Center of Problems of Chemical Physics and Medicinal ChemistryChernogolovka, Russia
T. N. Gavrishova
Federal Research Center of Problems of Chemical Physics and Medicinal ChemistryChernogolovka, Russia
P. V. Kitina
Faculty of Basic Physicochemical Engineering, Moscow State UniversityMoscow, Russia
I. V. Soulimenkov
Branch of Semenov Federal Research Center for Chemical PhysicsChernogolovka, Russia
References
- Shen J., Masaoka H., Tsuchiya K., Ogino K. // Polymer J. 2008. V. 40. P. 421.
- Gao L., Schloemer T.H., Zhang F., Chen Xi., Xiao Ch., Zhu K., Sellinger A. // Appl. Energy Mater. 2020. V. 3. P. 4492.
- Liu H., He B., Lu H., Tang R., Wu F., Zhong Ch. et al. // Sustainable Energy Fuels. 2022. V. 6. P. 371.
- Баран А., Плотниеце А., Соболев А., Виганте Б., Гостева М., Ольховик В. // ХГС. 2012. С. 305.
- Zheng Ya., Huo Ji., Xiao Sh., Shi H., Ma D., Tang B.Zh. // Org. Electronics. 2022. V. 101. P. 106411.
- Kwon H., Kang S., Park Su., Park Sa., Lee H., Lee S. et al. // Mol. Cryst. Liquid Cryst. 2023. V. 762. P. 21.
- Gu J., Yulan W., Chen W.-Q., Dong X.-Z., Duan X.-M., Kawata S. // New J. Chem. 2007. V. 31. P. 63.
- Wang Z., Nesterov V.N., Borbulevych O.Y., Clark R.D., Antipin M.Y., Timofeeva T. V. // Acta Crystallogr. 2001. V. C57. P. 1343.
- Oloub M., Hosseinzadeh R., Tajbakhsh M., Mohadjerani M. // RSC Adv. 2022. V. 12. P. 26201.
- Marotta G., Reddy M.A., Singh S.P., Islam A., Han L., De Angelis F. et al. // Appl. Mater. Interfaces. 2013. V. 5. P. 9635.
- Balsukuri N., Gupta I. // Dyes and Pigments. 2017. V. 144. P. 223.
- Cui Ya., Li F., Zhang Xi. // Chem. Commun. 2021. V. 57. P. 3275.
- Будыка М.Ф., Поташова Н.И., Гавришова Т.Н., Ли В.М. // Химия высоких энергий. 2008. Т. 42. С. 497.
- Будыка М.Ф., Поташова Н.И., Гавришова Т.Н., Ли В.М. // Химия высоких энергий. 2012. Т. 46. С. 369.
- Wu Y., Zhu Y., Yao C., Zhan J., Wu P., Han Z. et al. // J. Mater. Chem. C. 2023. V. 11. P. 15393.
- Ли В.М., Гавришова Т.Н., Будыка М.Ф. // ЖОрХ. 2012. Т. 48. С. 826.
- Li Y.-H., Zhou B., Shi Yi-M., Xun Yu-P., Yang Y.-H., Yang L.-J. // Chem. Biol. Drug Des. 2018. V. 92. P. 1206.
- Гавришова Т.Н., Ли В.М., Садыкова К.Ф., Будыка М.Ф. // Известия АН Сер. Хим. 2011. С. 1470.
- Liu L.-X., Wang X.-Q., Zhou B., Yang L.-J., Li Y., Zhang H.-B., Yang X.-D. // Sci. Rep. 2015. V. 5. P. 13101.
- Dodonov A.F., Kozlovski V.I., Soulimenkov I.V., Raznikov V.V., Loboda A.V., Zhen Z. et al. // Eur. J. Mass Spectrom. 2000. V. 6. P. 481.
- Becker H. D. // Chem. Rev. 1993. V. 93. P. 145.
- Frisch M.J., Trucks G.W., Schlegel H.B. et al. Gaussian, Inc., Wallingford CT, 2013.
- Mazzucato U., Momicchioli F. // Chem. Rev. 1991. V. 91. P. 1679.
- Braslavsky S.E., Fron E., Rodriguez H.B., Roman E.S., Scholes G.D., Schweitzer G. et al. // Photochem. Photobiol. Sci. 2008. V. 7. P. 1444.
- Chen C., Chong K.C., Pan Y., Qi G., Xu S., Liu B. // ACS Materials Lett. 2021. V. 3. P. 1081.
- Fischer E. // J. Phys. Chem. 1967. V. 71. P. 3704.
- Будыка М.Ф., Гавришова Т.Н., Ли В.М., Поташова Н.И. // Химия высоких энергий. 2016. Т. 50. С. 208.
- Galiazzo G., Bortolus P., Gennari G. // Gazz. Chim. Ital. 1990. V. 120. P. 581.
- Deschryver F.C., Collart P., Goedeweeck R., Swinnen A.M., Vandendriessche J., Vanderauweraer M. // Acc. Chem. Res. 1987. V. 20. P. 159.
- Разумов В.Ф., Алфимов М.В. // Журн. науч. и прикл. фотографии. 2003. Т. 48. С. 28.
- Budyka M.F., Gavrishova T.N., Li V.M., Potashova N.I., Fedulova J.A. // Spectrochim. Acta Part A. 2022. V. 267. P. 120565.
- Budyka M.F., Gavrishova T.N., Li V.M., Tovstun S.A. // Spectr. Acta Part A. 2024. V. 320. P. 124666.
- Budyka M.F. // Int J Quantum Chem. 2024. V. 124. e27264.
Supplementary files
