title: Three Short Stories about Hexaarylbenzene-Porphyrin Scaffolds.
abstract: 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.
authors.affiliation: Department Chemie und Pharmazie &, Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander-Universität Erlangen-Nürnberg, Henkestrasse 42, 91054, Erlangen, Germany.
authors.forename: Dominik
authors.initials: D
authors.lastname: Lungerich
authors.affiliation: Department Chemie und Pharmazie, Friedrich-Alexander-Universität Erlangen-Nürnberg, Egerlandstrasse 3, 91058, Erlangen, Germany.
authors.forename: Jakob F
authors.initials: JF
authors.lastname: Hitzenberger
authors.affiliation: Department Chemie und Pharmazie &, Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander-Universität Erlangen-Nürnberg, Henkestrasse 42, 91054, Erlangen, Germany.
authors.forename: Wolfgang
authors.initials: W
authors.lastname: Donaubauer
authors.affiliation: Department Chemie und Pharmazie, Friedrich-Alexander-Universität Erlangen-Nürnberg, Egerlandstrasse 3, 91058, Erlangen, Germany.
authors.forename: Thomas
authors.initials: T
authors.lastname: Drewello
authors.affiliation: Department Chemie und Pharmazie &, Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander-Universität Erlangen-Nürnberg, Henkestrasse 42, 91054, Erlangen, Germany.
authors.forename: Norbert
authors.identifier: http://orcid.org/0000-0002-5673-8181
authors.initials: N
authors.lastname: Jux
keywords: luminescence; mass spectrometry; microwave chemistry; porphyrinoids; synthesis design