Three Short Stories about Hexaarylbenzene–Porphyrin Scaffolds. Issue 47 (18th October 2016)

• Record Type: Journal Article
• Authors: Lungerich, Dominik; Hitzenberger, Jakob F.; Donaubauer, Wolfgang; Drewello, Thomas; Jux, Norbert
• Is Part Of: Chemistry. Volume 22:Issue 47(2016)
• Page Start: 16755
• Page End: 16759
• Publication Date: 2016-10-18
• Subjects: luminescence -- mass spectrometry -- microwave chemistry -- porphyrinoids -- synthesis design; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201603789
• Languages: English
• ISSNs: 0947-6539

Abstract

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. Abstract : Hexaarylbenzene (HAB) ‐substituted (tetrabenzo)porphyrins were found to have useful properties for various applications, such as calibrants for (MA)LDI instruments, as strong red‐ and near‐ infrared light emitters, and as precursors to large superbenzene‐porphyrin light‐harvesting architectures.