Effects of position (? or ?) and linker heteroatom (O or S) of substituent on the photophysicochemical behavior of poly(oxyethylene) substituted ZnPcs and assessment of J-aggregation or protonation using TD-DFT computations

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dc.authoridAYHAN, MEHMET MENAF/0000-0001-5367-2220
dc.authoridOzpinar, Gul/0000-0002-6913-183X
dc.contributor.authorAyhan, Mehmet Menaf
dc.contributor.authorOzpinar, Gul Altinbas
dc.contributor.authorDurmus, Mahmut
dc.contributor.authorGurek, Ayse Gul
dc.date.accessioned2025-01-27T20:50:32Z
dc.date.available2025-01-27T20:50:32Z
dc.date.issued2013
dc.departmentÇanakkale Onsekiz Mart Üniversitesi
dc.description.abstractA series of zinc phthalocyanines (ZnPcs) tetra-substituted with 1,3-di[2-(2-ethoxyethoxy)ethoxy]-2-propanol (1a) or 1,3-di[2-(2-ethoxyethoxy)ethoxy]-2-propanethiol (1b) at peripheral (beta) (6a-b) and non-peripheral (a) (7a-b) positions have been synthesized and characterized. The spectroscopic, photophysical (fluorescence quantum yields and lifetimes) and photochemical (singlet oxygen generation and photodegradation) properties of these newly synthesized phthalocyanines have been investigated in DMSO. The effects of the position of the substituents on the phthalocyanine skeleton and the nature of the linker heteroatom on their spectroscopic, photophysical and photochemical properties have been determined. The quenching behavior of the zinc phthalocyanines by 1,4-benzoquinone has been studied in DMSO. All of the zinc(II) Pc complexes (6a-b and 7a-b) showed similar electronic absorption spectra in various solvents (chloroform, dichloromethane, DMF, DMSO, THF and toluene). However, complex 7a gave an extra red-shifted band at 742 nm in chloroform and dichloromethane. DFT and TD-DFT computations were performed on the model structures (8a-d, p-8a-d and 9a-d) to find out the cause of the extra red-shifted Q band (J-type aggregation or protonation of the Pc ring). The computational results showed that monoprotonation of a meso nitrogen atom leads to the formation of this extra band. Photophysical and photochemical measurements indicated that these newly synthesized ZnPc derivatives are promising candidates for use as photosensitizers in the application of PDT.
dc.description.sponsorshipDeutsche Forschungsgemeinschaft
dc.description.sponsorshipWe thank the Computer-Chemie-Centrum, Excellence Cluster Engineering of Advanced Materials (funded by the Deutsche Forschungsgemeinschaft) and TUBITAK ULAKBIM, High Performance and Grid Computing Center (TR-Grid e-Infrastructure) for the calculations reported in the theoretical part of this paper. We would like to give special thanks to Prof. Dr Timothy Clark.
dc.identifier.doi10.1039/c3dt51549d
dc.identifier.endpage14904
dc.identifier.issn1477-9226
dc.identifier.issn1477-9234
dc.identifier.issue41
dc.identifier.pmid23995014
dc.identifier.scopus2-s2.0-84885129841
dc.identifier.scopusqualityQ2
dc.identifier.startpage14892
dc.identifier.urihttps://doi.org/10.1039/c3dt51549d
dc.identifier.urihttps://hdl.handle.net/20.500.12428/25515
dc.identifier.volume42
dc.identifier.wosWOS:000325369200031
dc.identifier.wosqualityQ1
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.language.isoen
dc.publisherRoyal Soc Chemistry
dc.relation.ispartofDalton Transactions
dc.relation.publicationcategoryinfo:eu-repo/semantics/openAccess
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WoS_20250125
dc.subjectPhotochemical Properties
dc.subjectPhotodynamic Therapy
dc.subjectPhthalocyanine
dc.subjectStabilities
dc.subjectFilms
dc.titleEffects of position (? or ?) and linker heteroatom (O or S) of substituent on the photophysicochemical behavior of poly(oxyethylene) substituted ZnPcs and assessment of J-aggregation or protonation using TD-DFT computations
dc.typeArticle

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