Metal or metal-free phthalocyanines containing morpholine substituents: synthesis, spectroscopic and photophysicochemical properties

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dc.authoridPiskin, Mehmet/0000-0002-4572-4905
dc.contributor.authorDemirbas, Umit
dc.contributor.authorPiskin, Mehmet
dc.contributor.authorDurmus, Mahmut
dc.contributor.authorKantekin, Halit
dc.date.accessioned2025-01-27T20:50:32Z
dc.date.available2025-01-27T20:50:32Z
dc.date.issued2022
dc.departmentÇanakkale Onsekiz Mart Üniversitesi
dc.description.abstractThe phthalonitrile (3) and its peripherally tetra 4-(3-morpholinophenoxy) substituted metal-free (4), lead(II) (5) and zinc(II) (6) phthalocyanine derivatives were synthesized. The structures of 3-6 were confirmed by FT-IR, H-1-NMR, MALDI-TOF mass, UV-vis and fluorescence spectral data. The solubility and aggregation behaviors of 4-6 were determined in dimethyl sulfoxide (DMSO), N,N-dimethylformamide (DMF), tetrahydrofuran (THF), chloroform (CHCl3) and dichloromethane (CH2Cl2). The observed sharp absorptions were evidence of formation of non-aggregated phthalocyanine species at the studied concentration. The effects of the substituent and central metal ions (metal-free, zinc or lead) on spectroscopic and photophysicochemical properties were determined. Their photophysicochemical properties such as fluorescence quantum yields and lifetimes, singlet oxygen generation and photodegradation quantum yields were investigated in DMSO. The fluorescence spectra of metal-free (4) and lead(II) (5) phthalocyanines were not recorded due to negligible fluorescence emissions of these phthalocyanines. The zinc(II) phthalocyanine (6) had 0.17 fluorescence quantum yield (phi(F)) and 1.42 fluorescence lifetime (tau(F)). The phthalocyanines (4-6) had 0.18, 0.41, 0.52 singlet oxygen quantum yields (phi(Delta)) and 0.51, 3.90, 0.46 photodegradation quantum yields (phi(Delta)), respectively. The zinc(II) phthalocyanine (6) in particular could be a potential Type II photosensitizer candidate for photodynamic therapy in cancer treatment.
dc.identifier.doi10.1080/00958972.2022.2102906
dc.identifier.endpage1255
dc.identifier.issn0095-8972
dc.identifier.issn1029-0389
dc.identifier.issue9-10
dc.identifier.scopus2-s2.0-85134615457
dc.identifier.scopusqualityQ3
dc.identifier.startpage1243
dc.identifier.urihttps://doi.org/10.1080/00958972.2022.2102906
dc.identifier.urihttps://hdl.handle.net/20.500.12428/25517
dc.identifier.volume75
dc.identifier.wosWOS:000829321900001
dc.identifier.wosqualityQ3
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherTaylor & Francis Ltd
dc.relation.ispartofJournal of Coordination Chemistry
dc.relation.publicationcategoryinfo:eu-repo/semantics/openAccess
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WoS_20250125
dc.subjectPhthalocyanine
dc.subjectmorpholinophenoxy
dc.subjectfluorescence
dc.subjectsinglet oxygen
dc.subjectphotosensitizer
dc.titleMetal or metal-free phthalocyanines containing morpholine substituents: synthesis, spectroscopic and photophysicochemical properties
dc.typeArticle

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