dc.contributor.author | Senge, Mathias | |
dc.contributor.author | Hohlfeld, Benjamin F. | |
dc.contributor.author | Flanagan, Keith J. | |
dc.contributor.author | Kulak, Nora | |
dc.contributor.author | Christmann, Mathias | |
dc.contributor.author | Wiehe, Arno | |
dc.date.accessioned | 2020-02-05T11:45:57Z | |
dc.date.available | 2020-02-05T11:45:57Z | |
dc.date.issued | 2019 | |
dc.date.submitted | 2019 | en |
dc.identifier.citation | Hohlfeld, B.F., Flanagan, K.J., Kulak, N., Senge, M.O., Christmann, M. & Wiehe, A., Synthesis of Porphyrinoids, BODIPYs, and (Dipyrrinato)ruthenium(II) Complexes from Prefunctionalized Dipyrromethanes, 2019, European Journal of Organic Chemistry, 2019, 25 | en |
dc.identifier.other | Y | |
dc.identifier.uri | https://onlinelibrary.wiley.com/doi/full/10.1002/ejoc.201900530 | |
dc.identifier.uri | http://hdl.handle.net/2262/91452 | |
dc.description.abstract | The introduction of functional groups into the mesoposition
of dipyrromethanes, boron-dipyrromethenes (BODIPYs) and
porphyrinoids, is of fundamental importance in designing such dye
systems for material sciences or photomedicine. One route that has
proven to be particularly useful in this respect is the nucleophilic
aromatic substitution (SNAr) on porphyrinoids and their precursors
carrying electron-withdrawing substituents. To further expand this
methodology, the potential of the 4-fluoro-3-nitrophenyl and the
3,4,5-trifluorophenyl moieties for the synthesis of functionalized
dipyrromethanes, BODIPYs, and porphyrinoids has been evaluated.
The 3,4,5-trifluorophenyl moiety proved not to be applicable in the
SNAr with nucleophiles. The introduction of the 4-fluoro-3-nitrophenyl
group, however, allowed fast and efficient SNAr with various amine
nucleophiles. The synthesized 4-amino-3-nitrophenyl-substituted
dipyrromethanes were successfully applied in the synthesis
BODIPYs and were tested in the synthesis of ‘trans’-A2B2 porphyrins
and A2B corroles. Furthermore, the dipyrromethanes - after oxidation
to the dipyrromethenes - were found to be suitable ligands for metal
ions giving access to functionalized ruthenium(II) metal complexes. | en |
dc.format.extent | 4020-4033 | en |
dc.language.iso | en | en |
dc.relation.ispartofseries | European Journal of Organic Chemistry; | |
dc.relation.ispartofseries | 2019; | |
dc.relation.ispartofseries | 25; | |
dc.rights | Y | en |
dc.subject | Porphyrinoids | en |
dc.subject | Dipyrromethanes | en |
dc.subject | BODIPYs | en |
dc.subject | Nucleophilic aromatic substitution | en |
dc.subject | Fluorine | en |
dc.subject | Ruthenium | en |
dc.title | Synthesis of Porphyrinoids, BODIPYs, and (Dipyrrinato)ruthenium(II) Complexes from Prefunctionalized Dipyrromethanes | en |
dc.type | Journal Article | en |
dc.contributor.sponsor | Science Foundation Ireland | en |
dc.type.supercollection | scholarly_publications | en |
dc.type.supercollection | refereed_publications | en |
dc.identifier.peoplefinderurl | http://people.tcd.ie/sengem | |
dc.identifier.rssinternalid | 206052 | |
dc.identifier.doi | http://dx.doi.org/10.1002/ejoc.201900530 | |
dc.rights.ecaccessrights | openAccess | |
dc.contributor.sponsorGrantNumber | IvP 13/IA/1894 | en |