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dc.contributor.authorSENGE, MATHIAS
dc.contributor.authorBLAU, WERNER
dc.date.accessioned2018-06-05T16:03:04Z
dc.date.available2018-06-05T16:03:04Z
dc.date.issued2011
dc.date.submitted2011en
dc.identifier.citationSenge, M. O.; Fazekas, M.; Pintea, M.; Zawadzka, M.; Blau, W. J., Synthesis of Unsymmetrical meso-Substituted Porphyrins, 1. 5,15-A2B2- and 5,15-A2BC-Type Porphyrins with Donor and Acceptor Groups for Use in Nonlinear Optics and Photodynamic Therapy, European Journal of Organic Chemistry, 2011, 2011, 5797 5816en
dc.identifier.otherY
dc.identifier.urihttp://hdl.handle.net/2262/82976
dc.descriptionPUBLISHEDen
dc.description.abstractDevelopment of new efficient synthetic strategies leading to more diversified substitution patterns of porphyrin rings is of great importance as it expands the potential applicability of these compounds and provides a more accurate way of tailoring their properties for a specific application. Changes in the electronic and conformational structures induced by different substituents are manifested by unique properties which are of interest for many applications ranging from amphiphilic porphyrins for photodynamic therapy, push-pull systems for optical applications, chiral systems useful in catalysis, to donor-acceptor systems suitable for electron transfer studies. Different chemical strategies were demonstrated for access to unsymetrically substituted porphyrins with nonequivalent ?- or meso substituents. For the latter we have adopted the functionalization of preformed porphyrins in order to obtain a diverse range of porphyrin structures with 5,15-A2B2 and 5,15-A2BC meso substitution patterns suitable for applications in optical limiting and photodynamic therapy. The functionalization of A2?type starting material via organolithium and palladium catalyzed crosscoupling reactions is an efficient means which enables the introduction of almost any desired meso substituent. We report on the nonlinear absorptive properties of our A2B2 and A2BC porphyrins and show that there is strong correlation between structural features and the optical limiting efficiency. The nonlinear optical studies indicate that the 5,15-A2B2 substitution pattern provides more promising candidates for use in optical limiting.en
dc.description.sponsorshipThis work was supported by grants from Science Foundation Ireland (SFI P.I. 09/IN.1/B2650) and the Health Research Board (HRB Translational Research Award 2007 TRA/2007/11). We are grateful to the Centre for Synthesis and Chemical Biology (CSCB) for HRMS measurements.en
dc.format.extent5797 5816en
dc.language.isoenen
dc.relation.ispartofseriesEuropean Journal of Organic Chemistry;
dc.relation.ispartofseries2011;
dc.rightsYen
dc.titleSynthesis of Unsymmetrical meso-Substituted Porphyrins, 1. 5,15-A2B2- and 5,15-A2BC-Type Porphyrins with Donor and Acceptor Groups for Use in Nonlinear Optics and Photodynamic Therapyen
dc.typeJournal Articleen
dc.type.supercollectionscholarly_publicationsen
dc.type.supercollectionrefereed_publicationsen
dc.identifier.peoplefinderurlhttp://people.tcd.ie/sengem
dc.identifier.peoplefinderurlhttp://people.tcd.ie/wblau
dc.identifier.rssinternalid78003
dc.rights.ecaccessrightsOpenAccess


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