Novel bis-ball-type double-decker phthalocyanines containing symmetric di-schiff base derivatives: Synthesis, spectroscopy, and photophysicochemical properties

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dc.authorid0000-0002-4572-4905
dc.contributor.authorMutlu, Fatih
dc.contributor.authorOzturk, Omer Faruk
dc.contributor.authorPiskin, Mehmet
dc.date.accessioned2026-02-03T12:02:40Z
dc.date.available2026-02-03T12:02:40Z
dc.date.issued2025
dc.departmentÇanakkale Onsekiz Mart Üniversitesi
dc.description.abstractIn this study, novel symmetric bis(oxy)-diphthalonitrile derivatives carrying di-Schiff base groups were designed and synthesized for various applications, including pharmaceuticals and photocatalysis. The compounds, 4,4 '((((1E, 1 ' E)-(1,4-phenylenebis(azanilylidene) bis(methanylylidene) bis(6-methoxy-2,1-phenylene))bis(oxy))diphthalonitrile) (2), and their ball-type bis-metal-free (3) and lutetium(III) phthalocyanine complex derivatives (4), were characterized by elemental analysis, FTIR, 1H NMR, 13C NMR, MALDI-TOF MS, and UV-vis spectroscopy (for bis-ball-type double-decker phthalocyanines 3 and 4). The solubility and aggregation behaviors of 2 and 3, containing electron donor and acceptor groups in the symmetric di-Schiff base framework, were studied in various solvents: polar protic, aprotic, borderline polar aprotic, and non-polar. These bis-ball-type doubledecker phthalocyanine derivatives exhibited high solubility without aggregation in all solvents studied, except hexane for 3 and 4, and water and toluene for 3. To assess their potential as photosensitizers for photocatalytic applications, their photophysical properties in DMSO and photochemical properties in DMSO and DMF were investigated. These bis-ball-type double-decker phthalocyanine derivatives exhibited absorption bands with high molar extinction coefficients in the therapeutic window, along with low but sufficient fluorescence quantum yields, lifetimes, and intersystem crossing probabilities. They also displayed adequate singlet oxygen production and high photostability. These photophysical and chemical properties make them promising candidates for various photocatalytic applications, including biological and biomedical imaging.
dc.description.sponsorshipanakkale Onsekiz Mart University Scientific Research Projects Coordination Unit [FDK-2024-4721]
dc.description.sponsorshipThis work was supported by Canakkale Onsekiz Mart University Scientific Research Projects Coordination Unit. Project Number: FDK-2024-4721.
dc.identifier.doi10.1016/j.molstruc.2025.142751
dc.identifier.issn0022-2860
dc.identifier.issn1872-8014
dc.identifier.scopus2-s2.0-105006826757
dc.identifier.scopusqualityQ1
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2025.142751
dc.identifier.urihttps://hdl.handle.net/20.500.12428/34816
dc.identifier.volume1343
dc.identifier.wosWOS:001507532100001
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherElsevier
dc.relation.ispartofJournal of Molecular Structure
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WOS_20260130
dc.subjectSymmetric Di-Schiff Base
dc.subjectBis-Ball-Type Double-Decker Phthalocyanine
dc.subjectSolute-Solvent Interactions
dc.subjectPhotostability
dc.subjectPhotophysicochemical Properties
dc.titleNovel bis-ball-type double-decker phthalocyanines containing symmetric di-schiff base derivatives: Synthesis, spectroscopy, and photophysicochemical properties
dc.typeArticle

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