Synthesis of perylene–porphyrin building blocks and rod-like oligomers for light-harvesting applications

Bromination of porphyrins (Review)

“…The high regioselectivity of bromination according to the previously proposed procedure [16] made it possible to substitute hydrogen by bromine in the molecule of compound 6 exclusively at the free meso positions of porphyrin and to leave the large perylene aromatic system unaffected [27]. Dimerization is observed as a side reaction during bromination of the porphyrin 8 with N-bromosuccinimide.…”

Self‐Assembled PDINH Supramolecular System for Photocatalysis under Visible Light

“…PDI (perylene-3,4,9,10-tetracarboxylic diimide) stands out among n-type organic semiconductors due to its excellent thermal/photo-stability, high electron affinity, and charge carrier mobilities. [14,15] Due to the unique optical and electronic properties of PDI, recently, various applications have been investigated, [16,17] such as fluorescence switches, [18] sensors, [19,20] organic field-effect transistors (OFETs), [21][22][23] light harvesting materials, [24,25] light emitting diodes, [26] and solar cells. [27][28][29] However, some of these above applications of PDI mainly focus on the isolated PDI molecule (i.e., monomeric PDI), the application in photocatalysis using self-assembled nanostructures of PDI has been rarely reported.…”

Oxygen Activation Chemistry of Pacman and Hangman Porphyrin Architectures Based on Xanthene and Dibenzofuran Spacers

“…Given that the etioporphyrin-type substitution patterns of the parent DPX and DPD systems are generally unstable to oxidizing conditions, owing to the unprotected meso positions on the porphyrin rings, it was reasoned that the construction of meso-substituted bisporphyrin Pacman derivatives might display higher catalase (and more generally, oxidative) efficiencies. Scheme 3 presents a modular and general synthetic route for the facile preparation of mesotetraaryl cofacial bisporphyrins affixed to xanthene (DTMPX ¼ ditrimesitylporitylporphyrin xanthene) or dibenzofuran (DTMPD ¼ ditrimesitylporphyrin dibenzofuran) scaffolds using Suzuki cross-coupling methods (140)(141)(142)(143)(144)(145)(146)(147)(148)(149)(150)(151)(152)(153)(154). The mesityl (mes) substituents incorporated into the Pacman motif provide steric bulk, as well as oxidative stability for high-valent metal oxo species (155,156).…”