A study was carried out on the spectral-luminescence and phosphorescence properties of an indotricarbocyanine dye with an ortho-phenylene bridge in the conjugation chain as well as two 300-Da polyethylene glycol (PEG) substituents (PD1) and its analog without PEG (PD2). The presence of the bulky PEG300 substituents in the dye structures was shown to alter the efficiency of singlet oxygen generation. The yield of singlet oxygen in ethanol for both dyes in the concentration range from 5∙10–8 to 10–5 M has a constant value γΔ = 0.031 ± 0.005 for PD1 and 0.050 ± 0.008 for PD2. An increasing value of γΔ from 0.022 ± 0.004 when Cdye = 2.6·10–7 M to 0.104 ± 0.016 when Cdye = 5.8·10–5 M was found in the concentration range from 10–7 to 10–5 M in low-polarity chloroform for PD2, whereas the quantum yield for PD1 with bulky substituents is invariant in this concentration range (0.032 ± 0.003). The increase in the singlet oxygen formation quantum yield with increasing concentration of PD2 in low-polarity chloroform is attributed to an increase in the fraction of contact ion pairs in solution and a heavy atom effect related to the Br– anion. The presence of two PEG300 chains in the structure of the cationic indotricarbocyanine dye (~770 Da) prevents the counterion from moving away from the cation of dye PD1 in low-polarity chloroform. Furthermore, the dye molecules are in the form of contact ion pairs at any concentration and it is hence difficult for the chromophore to interact with dissolved oxygen due to steric hindrance.
Similar content being viewed by others
References
E. S. Voropai and M. P. Samtsov, J. Appl. Spectrosc., 65, No. 2, 369–377 (1995); doi: https://doi.org/10.1007/BF02606495.
M. P. Samtsov, S. A. Tikhomirov, L. S. Lyashenka, D. S. Tarasau, O. V. Buganov, V. A. Galievsky, A. S. Stasheuski, and E. S. Voropay, J. Appl. Spectrosc., 80, No. 2, 170–175 (2013).
M. P. Samtsov, E. S. Voropai, K. N. Kaplevsky, D. G. Melnikau, L. S. Lyashenko, and Yu. P. Istomin, J. Appl. Spectrosc., 76, No. 4, 576–582 (2009).
A. A. Ishchenko and A. T. Syniugina, Theor. Exp. Chem., 58, 373–401 (2023); doi: https://doi.org/10.1007/s11237023097549.
D. M. Dereje, C. Pontremoli, M. J. Moran Plata, S. Visentin, and N. Barbero, Photochem. Photobiol. Sci., 21, 397–419 (2022); doi: https://doi.org/10.1007/s43630022001756.
N. Lange, W. Szlasa, J. Saczko, and A. Chwilkowska, Pharmaceutics, 13, 818 (2021); doi: https://doi.org/10.3390/pharmaceutics13060818.
S. Kwiatkowski, B. Knap, D. Przystupski, J. Saczko, E. Kędzierska, K. Knap-Czop, J. Kotlińska, O. Michel, K. Kotowski, and J. Kulbacka, Biomed. Pharm., 106, 1098–1107 (2018); doi: https://doi.org/10.1016/j.biopha.2018.07.049.
E. S. Voropai, M. P. Samtsov, K. N. Kaplevskii, A. A. Lugovskii, and E. N. Aleksandrova, J. Appl. Spectrosc., 71, 180–186 (2004).
M. P. Samtsov, E. S. Voropai, D. G. Mel'nikov, L. S. Lyashenko, A. A. Lugovskii, and Yu. P. Istomin, J. Appl. Spectrosc., 77, No. 3, 406–412 (2010).
A. A. Lugovski, M. P. Samtsov, K. N. Kaplevsky, D. S. Tarasau, E. S. Voropay, P. T. Petrov, and Y. P. Istomin, J. Photochem. Photobiol. A: Chem., 316, 31–36 (2016); doi: https://doi.org/10.1016/j.jphotochem.2015.10.008.
M. P. Samtsov, D. S. Tarasov, A. S. Goryashchenko, N. I. Kazachkina, V. V. Zherdeva, A. P. Savitskii, and I. G. Meerovich, Zh. Bel. Gos. Univ., Fizika, No. 1, 33–40 (2018).
M. P. Samtsov, D. S. Tarasov, E. S. Voropai, L. S. Lyashenko, P. T. Petrov, V. M. Nasek, A. O. Savin, and R. D. Zil'berman, Zh. Bel. Gos. Univ., Fizika, No. 1, 19–26 (2019).
N. B. Bel'ko, M. P. Samtsov, and D. S. Tarasov, Zh. Bel. Gos. Univ., Fizika, No. 3, 17–23 (2020).
D. S. Tarasov, M. P. Samtsov, and N. N. Krasnoperov, Zh. Bel. Gos. Univ., Fizika, No. 2, 4–11 (2022)
A. J. Gordon and R. A. Ford, The Chemist's Companion, Wiley, New York (1972).
A. S. Stashevskii, V. A. Galievskii, and B. M. Dzagarov, Pribory Metody Izmerenii, 2, No. 1, 25 (2011).
K. N. Kaplevskii, M. P. Samtsov, A. S. Stashevskii, V. A. Galievskii, D. S. Tarasov, and E. S. Voropai, Vestn. Bel. Gos. Univ., Ser. 1: Fiz. Mat. Inform., No. 2, 7–11 (2012).
P. K. Frederiksen, S. P. McIlroy, C. B. Nielsen, I. Nikolajsen, E. Skovsen, M. Jørgensen, K. V. Mikkelsen, and P. R. Ogilby, J. Am. Chem. Soc., 127, 255–269 (2005); doi: https://doi.org/10.1021/ja0452020.
M. P. Samtsov, E. S. Voropai, K. N. Kaplevskii, and D. G. Mel'nikov, J. Appl. Spectrosc., 75, No. 5, 692–699 (2008).
M. P. Samtsov, D. S. Tarasau, A. S. Stashevskii, K. N. Kaplevsky, and E. S. Voropay, J. Appl. Spectrosc., 81, No. 1, 214–221 (2014).
E. S. Voropai, M. P. Samtsov, and K. N. Kaplevskii, J. Appl. Spectrosc., 70, 721–728 (2003).
T. Welton and C. Reichadt, Solvents and Solvent Effects in Organic Chemistry, John Wiley & Sons, Weinheim (2011).
I. R. Gould, R. H. Young, R. E. Moody, and S. J. Farid, J. Phys. Chem., 95, No. 5, 2068–2080 (1991).
X. Yang, Z. Zaitsev, B. Sauerwein, S. Murphy, and G. B. Schuster, J. Am. Chem. Soc., 114, No. 2, 793–794 (1992); doi: https://doi.org/10.1021/ja00028a075.
Y. Marcus and G. Hefter, Chem. Rev., 106, No. 11, 4585–4621 (2006); doi: https://doi.org/10.1021/cr040087x.
A. S. Tatikolov, L. A. Shvedova, N. A. Derevyanko, A. A. Ishchenko, and V. A. Kuzmin, Chem. Phys. Lett., 190, Nos. 3–4, 291–297 (1992); doi: https://doi.org/10.1016/00092614(92)853417.
A. V. Odinokov, M. V. Bazilevskii, N. Kh. Petrov, A. K. Chibisov, and M. V. Alfimov, High Energy Chem., 44, 376–382 (2010); doi: https://doi.org/10.2234/S0018143910050048.
V. A. Kuz'min, A. P. Darmanyan, V. I. Shirokova, M. A. Al'perovich, and I. N. Levkoev, Izv. Akad. Nauk SSSR, Ser. Khim., No. 3, 581–586 (1978).
N. Derkaoui, S. Said, Y. Grohens, R. Olier, and M. Privat, J. Colloid Interface Sci., 305, 330–338 (2007); doi: https://doi.org/10.1016/j.jcis.2006.10.008.
B. Heymann and H. Grubmüller, Chem. Phys. Lett., 307, Nos. 5–6, 425–432 (1999), doi: 1016/S00092614(99)00531X.
Y. Hu, J. Xie, Y. W. Tong, and C. H. Wang, J. Control. Rel., 118, No. 1, 7–17 (2007); doi: https://doi.org/10.1016/j.jconrel.2006.11.028.
M. T. Peracchia, C. Vanthier, C. Passirani, P. Couvreur, and D. Labarre, Life Sci., 61, No. 7, 749–761 (1997), doi: https://doi.org/10.1016/S00243205(97)005390.
S. D. Li and J. Huang, J. Control. Rel., 145, No. 3, 178–181 (2010); doi: 10.1016%2Fj.jconrel.2010.03.016.
Y. Gun, H. Yuan, W. L. Rice, A. T. Kumar, C. J. Goergen, K. Jokivarsi, and L. Josephson, J. Am. Chem. Soc., 134, No. 47, 19338–19341 (2012); doi: https://doi.org/10.1021/ja309085b.
Author information
Authors and Affiliations
Additional information
Translated from Zhurnal Prikladnoi Spektroskopii, Vol. 90, No. 5, pp. 738–746, September–October, 2023
Rights and permissions
Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.
About this article
Cite this article
Samtsov, M.P., Tarasov, D.S. & Voropay, E.S. Singlet Oxygen Generation by an Indotricarbocyanine Dye with Bulky Substituents. J Appl Spectrosc 90, 1029–1036 (2023). https://doi.org/10.1007/s10812-023-01628-1
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10812-023-01628-1