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Functional alcohol-soluble double-decker phthalocyanines: synthesis, characterization, electrochemistry and peripheral metal ion binding

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dc.contributor.authorsYarasir, Meryem N.; Kandaz, Mehmet; Koca, Atif; Salih, Bekir
dc.date.accessioned2022-03-12T17:21:56Z
dc.date.available2022-03-12T17:21:56Z
dc.date.issued2006
dc.description.abstractIn this study we report the preparation, physical characterization and electrochemistry of peripherally functionalized substituted ionophore double-decker lanthanide phthalocyanines, lanthanide bis-[(4,4',4,4')-tetrakis-(6-hydroxyhexylthio)phthalocyaninates], {M[Pc(S-C6H13OH)(4)](2)} (M = Pr-III, Yb-III, and Lu-III). All benzenes on the double-decker phthalocyanines are functionalized with hydroxyhexylsulfanyl moieties for potential use as metal ion binding and surface anchors. The double-decker phthalocyanines synthesized from the anhydrous metal salts {Ln(acac)(3)} and the corresponding 4-(6-hydroxyhexylthio)-1,2-dicyanobenzene exhibit ion-specific optical changes in the presence of Ag+ and Pd2+. Thio donors of the complexes coordinate to Ag+ and Pd2+ to give 4:1 metal-phthalocyanine complexes. Newly synthesized lanthanide double-decker phthalocyanines are soluble in methanol (MeOH), ethanol (EtOH), tetrahydrofuran (THF), dimethylformamide (DMF), dimethylsulfoxide (DMSO), chloronapthalene, quinoline and less soluble in i-PrOH and acetonitrile. Electrochemical studies reveal that all lanthanide-base complexes undergo ligand-based redox processes. The smaller HOMO-LUMO gaps of the complexes indicate the existence of strong pi-orbital interactions between the rings of the sandwich. The newly synthesized compounds have been characterized by elemental analysis, FTIR, H-1 and C-13 NMR, MS (ESI and MALDI-TOF), UV-vis and EPR spectral data. Copyright (c) 2006 Society of Porphyrins & Phthalocyanines.
dc.identifier.doi10.1142/S1088424606000375
dc.identifier.eissn1099-1409
dc.identifier.issn1088-4246
dc.identifier.urihttps://hdl.handle.net/11424/228379
dc.identifier.wosWOS:000243018100003
dc.language.isoeng
dc.publisherWORLD SCI PUBL CO INC
dc.relation.ispartofJOURNAL OF PORPHYRINS AND PHTHALOCYANINES
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.subjectlanthanides
dc.subjectphthalocyanines
dc.subjectelectrochemistry
dc.subjectaggregation
dc.subjectmetal sensor
dc.subjectionophore
dc.subjectLANGMUIR-BLODGETT-FILMS
dc.subjectRARE-EARTH COMPLEXES
dc.subjectSPECTROSCOPIC PROPERTIES
dc.subjectDINUCLEAR COMPLEXES
dc.subjectNI COMPLEX
dc.subject(E,E)M M
dc.subjectPART 4
dc.subjectBEHAVIOR
dc.subjectLIGAND
dc.subjectMONO
dc.titleFunctional alcohol-soluble double-decker phthalocyanines: synthesis, characterization, electrochemistry and peripheral metal ion binding
dc.typearticle
dspace.entity.typePublication
local.avesis.id0b0cde78-400a-460b-b215-092432f0ed7e
local.import.packageSS17
local.indexed.atWOS
local.indexed.atSCOPUS
local.journal.numberofpages12
oaire.citation.endPage1033
oaire.citation.issue8
oaire.citation.startPage1022
oaire.citation.titleJOURNAL OF PORPHYRINS AND PHTHALOCYANINES
oaire.citation.volume10

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