Heavy Atom-Enhanced Photooxidation Performance of Carbazole-Substituted BODIPY Dyes

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dc.authorid0000-0002-0840-4953
dc.authorid0000-0002-7935-3954
dc.authorid0009-0005-9038-2229
dc.authorid0000-0001-7939-5380
dc.authorid0000-0003-4448-1101
dc.contributor.authorOzdemir, Mucahit
dc.contributor.authorSevimli, Esra
dc.contributor.authorOzan, Gulsema
dc.contributor.authorSalan, Umit
dc.contributor.authorYalcin, Bahattin
dc.contributor.authorKoksoy, Baybars
dc.date.accessioned2026-02-08T15:14:46Z
dc.date.available2026-02-08T15:14:46Z
dc.date.issued2025
dc.departmentBursa Teknik Üniversitesi
dc.description.abstractIn this study, halogenated BODIPYs (C-Br-2-BDPY and C-I-2-BDPY) bearing a carbazole group at the meso position are synthesized and characterized using various spectroscopic techniques. Single-crystal X-ray diffraction analysis of the C-I-2-BDPY revealed that it crystallizes in a triclinic crystal system with a P-1 space group. The optical properties, singlet oxygen generation capacities, and photocatalytic activities of the BODIPY derivatives are evaluated with respect to juglone synthesis. While the nonhalogenated BODIPY (C-BDPY) exhibit negligible singlet oxygen generation (Phi(Delta) < 0.05), the iodinated (C-I-2-BDPY) and brominated (C-Br-2-BDPY) derivatives demonstrate considerably higher singlet oxygen quantum yields of 0.82 and 0.73, respectively. In the photooxidation reaction of 1,5-dihydroxynaphthalene (DHN) to juglone, these halogenated BODIPY compounds achieve conversion yields of 62.6% for C-Br-2-BDPY and 87.8% for C-I-2-BDPY within one hour. The turnover number values of the BODIPY photosensitizers show a continuous increase over time, indicating sustained product formation, whereas the turnover frequency values gradually decline, reflecting the decrease in reaction rate as the process progress. Density functional theory calculations support the experimental results by demonstrating that the presence of heavy atoms facilitates intersystem crossing and enhances the thermodynamic feasibility of the photooxidation reactions.
dc.description.sponsorshipCommission of Scientific Research Project
dc.description.sponsorshipThe numerical calculations reported in this paper were fully performed at TUBITAK ULAKBIM, High Performance and Grid Computing Center (TRUBA resources). This work was supported by the Research Foundation of Marmara University, Commission of Scientific Research Project (BAPKO) ADEP ADF-2022-10738.
dc.identifier.doi10.1002/ejoc.202500797
dc.identifier.issn1434-193X
dc.identifier.issn1099-0690
dc.identifier.issue43
dc.identifier.scopus2-s2.0-105017386260
dc.identifier.scopusqualityQ2
dc.identifier.urihttps://doi.org/10.1002/ejoc.202500797
dc.identifier.urihttps://hdl.handle.net/20.500.12885/5420
dc.identifier.volume28
dc.identifier.wosWOS:001584482700001
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherWiley-V C H Verlag Gmbh
dc.relation.ispartofEuropean Journal of Organic Chemistry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzWOS_KA_20260207
dc.subjectBODIPY
dc.subjectcarbazoles
dc.subjectjuglone
dc.subjectphotocatalysis
dc.subjectphotooxidation
dc.titleHeavy Atom-Enhanced Photooxidation Performance of Carbazole-Substituted BODIPY Dyes
dc.typeArticle

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