The effect of molecular structure of chlorin photosensitizers on photo-bleaching of 1,3-diphenylisobenzofuran—the possible evidence of iodine reactive species formation
In this short communication, we focus on the ability of chlorin e$_{6}$ photosensitizers (PSs) with one, two or three cationic groups to generate singlet oxygen species ($^{1}$O$_{2}$) in an apolar model medium, viz. 1-octanol (OctOH). The quantum yield of $^{1}$O$_{2}$ ($\Phi _{\Delta }$) is determ...
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Académie des sciences
2022-03-01
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| Series: | Comptes Rendus. Chimie |
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| Online Access: | https://comptes-rendus.academie-sciences.fr/chimie/articles/10.5802/crchim.158/ |
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| author | Kustov, Andrey Morshnev, Philipp Kukushkina, Natal’ya Krestyaninov, Mikhail Smirnova, Nataliya Berezin, Dmitry Kokurina, Galina Belykh, Dmitry |
| author_facet | Kustov, Andrey Morshnev, Philipp Kukushkina, Natal’ya Krestyaninov, Mikhail Smirnova, Nataliya Berezin, Dmitry Kokurina, Galina Belykh, Dmitry |
| author_sort | Kustov, Andrey |
| collection | DOAJ |
| description | In this short communication, we focus on the ability of chlorin e$_{6}$ photosensitizers (PSs) with one, two or three cationic groups to generate singlet oxygen species ($^{1}$O$_{2}$) in an apolar model medium, viz. 1-octanol (OctOH). The quantum yield of $^{1}$O$_{2}$ ($\Phi _{\Delta }$) is determined indirectly by the chemical method for seven synthesized PSs using 1,3-diphenylisobenzofuran (DPBF) as a singlet oxygen trap. The $\Phi _{\Delta }$ values of four PSs with one or two cationic groups occupying opposite positions in the macrocycle are equal to 0.6, which is nearly identical to the values obtained by the time-resolved fluorescence spectroscopy method. In contrast, three PSs containing a 3(1),3(2)-bis-(N,N,N-trimethylaminomethylvinyl) iodide fragment with two adjacent cationic groups have an abnormally high quantum yield reaching 0.8. It is apparent that this phenomenon results from faster trap oxidation induced by radical reactions leading to molecular iodine formation. |
| format | Article |
| id | doaj-art-522830602c014546b860d5d39486d83f |
| institution | Kabale University |
| issn | 1878-1543 |
| language | English |
| publishDate | 2022-03-01 |
| publisher | Académie des sciences |
| record_format | Article |
| series | Comptes Rendus. Chimie |
| spelling | doaj-art-522830602c014546b860d5d39486d83f2025-02-07T13:31:13ZengAcadémie des sciencesComptes Rendus. Chimie1878-15432022-03-0125G19710210.5802/crchim.15810.5802/crchim.158The effect of molecular structure of chlorin photosensitizers on photo-bleaching of 1,3-diphenylisobenzofuran—the possible evidence of iodine reactive species formationKustov, Andrey0https://orcid.org/0000-0002-3553-6206Morshnev, Philipp1https://orcid.org/0000-0003-2119-605XKukushkina, Natal’ya2https://orcid.org/0000-0002-0359-5084Krestyaninov, Mikhail3https://orcid.org/0000-0001-7834-6763Smirnova, Nataliya4Berezin, Dmitry5https://orcid.org/0000-0001-5814-9105Kokurina, Galina6Belykh, Dmitry7https://orcid.org/0000-0001-8553-5140G.A. Krestov Institute of Solution Chemistry, Russian Academy of Sciences, Academicheskaya str., 1, Ivanovo, 153045, Russia; Ivanovo State University of Chemistry and Technology, Research Institute of Macroheterocycles, Sheremetevsky av., 7, Ivanovo, 153000, RussiaG.A. Krestov Institute of Solution Chemistry, Russian Academy of Sciences, Academicheskaya str., 1, Ivanovo, 153045, Russia; Ivanovo State University of Chemistry and Technology, Research Institute of Macroheterocycles, Sheremetevsky av., 7, Ivanovo, 153000, RussiaG.A. Krestov Institute of Solution Chemistry, Russian Academy of Sciences, Academicheskaya str., 1, Ivanovo, 153045, Russia; Ivanovo State University of Chemistry and Technology, Research Institute of Macroheterocycles, Sheremetevsky av., 7, Ivanovo, 153000, RussiaG.A. Krestov Institute of Solution Chemistry, Russian Academy of Sciences, Academicheskaya str., 1, Ivanovo, 153045, RussiaG.A. Krestov Institute of Solution Chemistry, Russian Academy of Sciences, Academicheskaya str., 1, Ivanovo, 153045, RussiaIvanovo State University of Chemistry and Technology, Research Institute of Macroheterocycles, Sheremetevsky av., 7, Ivanovo, 153000, RussiaIvanovo State University of Chemistry and Technology, Research Institute of Macroheterocycles, Sheremetevsky av., 7, Ivanovo, 153000, RussiaInstitute of Chemistry of Komi Science Centre of the Ural Branch of Russian Academy of Sciences, Pervomaiskaya str., 48, Syktyvkar, 167000, RussiaIn this short communication, we focus on the ability of chlorin e$_{6}$ photosensitizers (PSs) with one, two or three cationic groups to generate singlet oxygen species ($^{1}$O$_{2}$) in an apolar model medium, viz. 1-octanol (OctOH). The quantum yield of $^{1}$O$_{2}$ ($\Phi _{\Delta }$) is determined indirectly by the chemical method for seven synthesized PSs using 1,3-diphenylisobenzofuran (DPBF) as a singlet oxygen trap. The $\Phi _{\Delta }$ values of four PSs with one or two cationic groups occupying opposite positions in the macrocycle are equal to 0.6, which is nearly identical to the values obtained by the time-resolved fluorescence spectroscopy method. In contrast, three PSs containing a 3(1),3(2)-bis-(N,N,N-trimethylaminomethylvinyl) iodide fragment with two adjacent cationic groups have an abnormally high quantum yield reaching 0.8. It is apparent that this phenomenon results from faster trap oxidation induced by radical reactions leading to molecular iodine formation.https://comptes-rendus.academie-sciences.fr/chimie/articles/10.5802/crchim.158/Antimicrobial photodynamic therapyCationic chlorin photosensitizerSinglet oxygen formation1,3-diphenylisobenzofuranReactive iodine species |
| spellingShingle | Kustov, Andrey Morshnev, Philipp Kukushkina, Natal’ya Krestyaninov, Mikhail Smirnova, Nataliya Berezin, Dmitry Kokurina, Galina Belykh, Dmitry The effect of molecular structure of chlorin photosensitizers on photo-bleaching of 1,3-diphenylisobenzofuran—the possible evidence of iodine reactive species formation Comptes Rendus. Chimie Antimicrobial photodynamic therapy Cationic chlorin photosensitizer Singlet oxygen formation 1,3-diphenylisobenzofuran Reactive iodine species |
| title | The effect of molecular structure of chlorin photosensitizers on photo-bleaching of 1,3-diphenylisobenzofuran—the possible evidence of iodine reactive species formation |
| title_full | The effect of molecular structure of chlorin photosensitizers on photo-bleaching of 1,3-diphenylisobenzofuran—the possible evidence of iodine reactive species formation |
| title_fullStr | The effect of molecular structure of chlorin photosensitizers on photo-bleaching of 1,3-diphenylisobenzofuran—the possible evidence of iodine reactive species formation |
| title_full_unstemmed | The effect of molecular structure of chlorin photosensitizers on photo-bleaching of 1,3-diphenylisobenzofuran—the possible evidence of iodine reactive species formation |
| title_short | The effect of molecular structure of chlorin photosensitizers on photo-bleaching of 1,3-diphenylisobenzofuran—the possible evidence of iodine reactive species formation |
| title_sort | effect of molecular structure of chlorin photosensitizers on photo bleaching of 1 3 diphenylisobenzofuran the possible evidence of iodine reactive species formation |
| topic | Antimicrobial photodynamic therapy Cationic chlorin photosensitizer Singlet oxygen formation 1,3-diphenylisobenzofuran Reactive iodine species |
| url | https://comptes-rendus.academie-sciences.fr/chimie/articles/10.5802/crchim.158/ |
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