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dc.contributor.authorSENGE, MATHIASen
dc.date.accessioned2015-05-06T10:17:14Z
dc.date.available2015-05-06T10:17:14Z
dc.date.issued2014en
dc.date.submitted2014en
dc.identifier.citationRogers, L, Burke-Murphy, E, Senge, MO, Simple Porphyrin Desymmetrization: 5,10,15,20-Tetrakis(3-hydroxyphenyl)porphyrin (mTHPP) as a Gateway Molecule for Peripheral Functionalization, EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 20, 2014, 4283-4294en
dc.identifier.issn1434-193Xen
dc.identifier.otherYen
dc.identifier.urihttp://hdl.handle.net/2262/73839
dc.descriptionPUBLISHEDen
dc.description.abstractAbstract: The rise in the demand towards unsymmetric porphyrin systems for use in applications such as photodynamic therapy and non-linear optics mandates a concomitant development of simple and practical syntheses thereof. A new methodology for the rapid generation of unsymmetrical porphyrins synthesized from the same common and easily accessible symmetric porphyrin starting material is discussed herein. A library of unsymmetric mTHPP [5,10,15,20- tetrakis(3-hydroxyphenyl)porphyrin] derivatives was synthesized in good yields through simple nucleophilic substitution, esterification and metal catalyzed cross-coupling reactions. The methodology was optimized to quickly generate a library of tailored unsymmetrical porphyrins for use in a variety of applications. Use of a common meso-aryl substituted porphyrin as starting material allowed an updating of the synthetic toolkit using a mixture of classical and modern chemistry. This approach was tested as a method for the synthesis of picketfence porphyrin mimics and gave such compounds in good yields and few synthetic steps. Likewise, employing simple nucleophilic substitution chemistry co-facial, ‘caged’ bisporphyrin systems were accessible in two synthetic steps.en
dc.description.sponsorshipThis work was supported by a grant from Science Foundation Ireland (P.I. 09/IN.1/B2650).en
dc.format.extent4283-4294en
dc.language.isoenen
dc.relation.ispartofseriesEUROPEAN JOURNAL OF ORGANIC CHEMISTRYen
dc.relation.ispartofseries20en
dc.rightsYen
dc.subjectporphyrinoids • nucleophilic substitution • tetrapyrroles • macrocycles • photodynamic therapyen
dc.subject.lcshporphyrinoids • nucleophilic substitution • tetrapyrroles • macrocycles • photodynamic therapyen
dc.titleSimple Porphyrin Desymmetrization: 5,10,15,20-Tetrakis(3-hydroxyphenyl)porphyrin (mTHPP) as a Gateway Molecule for Peripheral Functionalizationen
dc.typeJournal Articleen
dc.contributor.sponsorScience Foundation Ireland (SFI)en
dc.type.supercollectionscholarly_publicationsen
dc.type.supercollectionrefereed_publicationsen
dc.identifier.peoplefinderurlhttp://people.tcd.ie/abdallmen
dc.identifier.peoplefinderurlhttp://people.tcd.ie/sengemen
dc.identifier.rssinternalid99860en
dc.identifier.doihttp://dx.doi.org/10.1002/ejoc.201402433en
dc.rights.ecaccessrightsopenAccess


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