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Hydrosoluble dendritic poly(ethylene oxide)s with zinc tetraphenylporphyrin branching points as photosensitizers

dc.rights.licenseopen
hal.structure.identifierLaboratoire de Chimie des Polymères Organiques [LCPO]
dc.contributor.authorWIROTIUS, Anne-Laure
hal.structure.identifierLaboratoire de Chimie des Polymères Organiques [LCPO]
dc.contributor.authorIBARBOURE, Emmanuel
hal.structure.identifierInstitut des Sciences Moléculaires [ISM]
dc.contributor.authorSCARPANTONIO, Luca
hal.structure.identifierLaboratoire de Chimie des Polymères Organiques [LCPO]
dc.contributor.authorSCHAPPACHER, Michel
hal.structure.identifierInstitut des Sciences Moléculaires [ISM]
dc.contributor.authorMCCLENAGHAN, Nathan D.
hal.structure.identifierLaboratoire de Chimie des Polymères Organiques [LCPO]
hal.structure.identifierTeam 1 LCPO : Polymerization Catalyses & Engineering
dc.contributor.authorDEFFIEUX, Alain
dc.date.accessioned2020
dc.date.available2020
dc.date.issued2013
dc.identifier.issn1759-9954
dc.identifier.urihttps://oskar-bordeaux.fr/handle/20.500.12278/20409
dc.description.abstractEnSynthesis of dendrimer-like star-branched poly(ethylene oxide)s (PEOs) with two and three generations having Zn(II) tetraphenylporphyrin (ZnTPP) moieties at the core and at each branching point has been successfully achieved through an iterative convergent approach harnessing "click chemistry". In the first step, a four-armed poly(ethylene oxide)star-shaped polymer was synthesized by the copper(I)-catalyzed azide-alkyne cycloaddition between alpha-azido poly(ethylene oxide) branches (N-3-PEO-OH) and 5,10,15,20-tetra(propargyloxyphenyl) Zn(II) porphyrin as the core. In the second step, a tetra-armed star PEO bearing 5-(4-phenoxy)-10,15,20-tris(propargyloxyphenyl) Zn(II) porphyrin at each branch end was prepared by divergence of the omega-hydroxyl PEO chain-ends through a Williamson-type etherification reaction. The resulting star PEO with 3 propargyl groups at each arm end was then subjected to a new "click chemistry" reaction with N-3-PEO-OH affording the dendrimer star-like PEO of second generation carrying 12 new omega-OH-PEO external branches attached to the four ZnTPP branching points. Repetition of the second step afforded the high molar mass third generation dendrimer-like PEO carrying 36 omega-OH PEO terminal branches with a uniform distribution of 17 zinc tetraphenylporphyrin moieties as internal branching points. The photophysical properties of the resulting polymers in organic or aqueous medium and their efficiency in singlet oxygen generation are reported.
dc.language.isoen
dc.publisherRoyal Society of Chemistry - RSC
dc.subject.enDELIVERY
dc.subject.enDENDRIMERS
dc.subject.enOXYGEN
dc.subject.enLIGATION
dc.subject.enPHOTODYNAMIC THERAPY AGENT
dc.subject.enSTAR POLYMERS
dc.subject.enAQUEOUS-SOLUTION
dc.subject.enPORPHYRIN CORE
dc.subject.enSITE ISOLATION
dc.subject.enAZIDE
dc.title.enHydrosoluble dendritic poly(ethylene oxide)s with zinc tetraphenylporphyrin branching points as photosensitizers
dc.typeArticle de revue
dc.identifier.doi10.1039/c2py20936e
dc.subject.halChimie/Polymères
bordeaux.journalPolymer Chemistry
bordeaux.page1903-1912
bordeaux.volume4
bordeaux.hal.laboratoriesLaboratoire de Chimie des Polymères Organiques (LCPO) - UMR 5629*
bordeaux.issue6
bordeaux.institutionBordeaux INP
bordeaux.institutionUniversité de Bordeaux
bordeaux.peerReviewedoui
hal.identifierhal-00846298
hal.version1
hal.origin.linkhttps://hal.archives-ouvertes.fr//hal-00846298v1
bordeaux.COinSctx_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.jtitle=Polymer%20Chemistry&rft.date=2013&rft.volume=4&rft.issue=6&rft.spage=1903-1912&rft.epage=1903-1912&rft.eissn=1759-9954&rft.issn=1759-9954&rft.au=WIROTIUS,%20Anne-Laure&IBARBOURE,%20Emmanuel&SCARPANTONIO,%20Luca&SCHAPPACHER,%20Michel&MCCLENAGHAN,%20Nathan%20D.&rft.genre=article


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