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1,2,3-Triazole incorporated coumarin carrying metal-free, Zn(II), Mg(II) phthalocyanines: Synthesis, characterization, theoretical studies, photophysical and photochemical properties

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dc.contributor.authorYALÇIN, BAHATTİN
dc.contributor.authorsOzdemir, Mucahit; Abliatipova, Aziza; Benian, Sueda; Yalcin, Bahattin; Salan, Umit; Durmus, Mahmut; Bulut, Mustafa
dc.date.accessioned2022-03-12T22:42:38Z
dc.date.available2022-03-12T22:42:38Z
dc.date.issued2020
dc.description.abstractIn this study, the preparation of two novel phthalonitrile compounds, 7-(propargyloxy)-3-(3,4-dicyanophenoxyphenyl)coumarin (1), and 7-(propargyloxy)-3-(2,3-dicyanophenoxy-phenyl)coumarin (2) were performed. Two new coumarinyl-1,2,3-triazole hybrids, (1-phenethy1-1H41,2,A-triazole 4 yl) 7 methyleneoxy 3 [F. (3,4 dicya nophenoxy)phenyl]-coumarin (3), and (1-phenethy1-1H-[1,2,3]-triazole 4 yl) 7 methyleneoxy 3 [F. (2,3 dicya nophenoxy)phenyl]-coumarin (4), were synthesized by the copper(I)-catalysed Huisgen 1,3-dipolar cycloaddition reaction of 2-(azidoethyl)benzene with terminal ethynyl bearing coumarin derivatives (1 or 2). These novel phthalonitrile derivatives (3 and 4) were converted into their peripheral (5-7) and non-peripheral (8-10) metal-free, zinc(II) and magnesium(II) phthalocyanine counterparts. The synthesized phthalocyanine derivatives are first examples on the phthalocyanine-coumarin derivatives bearing triazole ring. The structures of all these novel compounds were characterized by variety of spectroscopic techniques including FT-IR, UV-vis, H-1 NMR, MALDI-TOF MS and elemental analysis. The photophysicochemical properties of all studied Pcs (5-10) were determined in dimethyl sulfoxide. The zinc(II) and magnesium(II) phthalocyanines bearing triazole containing coumarin substituents appear to be useful as Type II photosensitizers because the singlet oxygen quantum yields ranged in acceptable values from 0.17 to 0.49 confirmed that these phthalocyanines can be suggested as photosensitizers in Photodynamic Therapy applications. Geometry optimization, frequency analysis and molecular orbital energy values of coumarin/triazole substituted phthalocyanine were performed in Density Functional Theory method using the B3LYP/LANL2DZ level of theory.
dc.identifier.doi10.1016/j.jphotochem.2020.112845
dc.identifier.eissn1873-2666
dc.identifier.issn1010-6030
dc.identifier.urihttps://hdl.handle.net/11424/236245
dc.identifier.wosWOS:000720331000009
dc.language.isoeng
dc.publisherELSEVIER SCIENCE SA
dc.relation.ispartofJOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.subject1,2,3-Triazole
dc.subjectPhthalocyanine
dc.subjectCoumarin
dc.subjectClick chemistry
dc.subjectPDT
dc.subjectSinglet oxygen
dc.subjectDensity functional theory
dc.subjectNONLINEAR-OPTICAL PROPERTIES
dc.subjectDERIVATIVES
dc.subjectZINC(II)
dc.subjectTETRA
dc.subjectANALOGS
dc.subjectDESIGN
dc.title1,2,3-Triazole incorporated coumarin carrying metal-free, Zn(II), Mg(II) phthalocyanines: Synthesis, characterization, theoretical studies, photophysical and photochemical properties
dc.typearticle
dspace.entity.typePublication
local.avesis.idc85367ef-16c2-4f8e-9b42-486fbd8b5835
local.import.packageSS17
local.indexed.atWOS
local.indexed.atSCOPUS
local.journal.articlenumber112845
local.journal.numberofpages11
local.journal.quartileQ2
oaire.citation.titleJOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY
oaire.citation.volume403
relation.isAuthorOfPublication6405e2ff-5dd8-487d-a639-ac5fcc0832bc
relation.isAuthorOfPublication.latestForDiscovery6405e2ff-5dd8-487d-a639-ac5fcc0832bc

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