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Three Short Stories about Hexaarylbenzene–Porphyrin Scaffolds
Author(s) -
Lungerich Dominik,
Hitzenberger Jakob F.,
Donaubauer Wolfgang,
Drewello Thomas,
Jux Norbert
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201603789
Subject(s) - porphyrin , condensation , combinatorial chemistry , photochemistry , free base , chemistry , polycyclic aromatic hydrocarbon , mass spectrometry , organic chemistry , physics , salt (chemistry) , chromatography , thermodynamics
A feasible two‐step synthesis and characterization of a full series of hexaarylbenzene (HAB) substituted porphyrins and tetrabenzoporphyrins is presented. Key steps represent the microwave‐assisted porphyrin condensation and the statistical Diels–Alder reaction to the desired HAB‐porphyrins. Regarding their applications, they proved to be easily accessible and effective high molecular mass calibrants for (MA)LDI mass spectrometry. The free‐base and zinc(II) porphyrin systems, as well as the respective tetrabenzoporphyrins, demonstrate in solid state experiments strong red‐ and near‐infrared‐light emission and are potentially interesting for the application in “truly organic” light‐emitting devices. Lastly, they represent facile precursors to large polycyclic aromatic hydrocarbon (PAH) substituted porphyrins. We prepared the first tetra‐hexa‐ peri ‐hexabenzocoronene substituted porphyrin, which represents the largest prepared PAH‐porphyrin conjugate to date.