An intramolecular oxidative aromatic coupling of meso-substituted porphyrins bearing electron-rich aromatics was the focus of investigation. The formation of C–C bond at [Formula: see text]-position for macrocycles bearing dimethoxynaphthalene moiety was achieved. It was established that Fe(ClO[Formula: see text]O induced only single cyclodehydrogenation whereas Fe(OTf)[Formula: see text] had the ability to remove four hydrogens and four electrons forming doubly-fused porphyrin. Both Fe(ClO[Formula: see text]O and Fe(OTf)[Formula: see text] were confirmed superior to FeCl[Formula: see text] as they ensured efficient oxidation process without concomitant chlorination of the products. We have proven that the trans-A[Formula: see text]B[Formula: see text]-porphyrin with two indole moieties do not form any stable products under such reaction conditions. The single fusion with dimethoxynaphthalene moiety has a comparable effect on absorption spectra [Formula: see text]. the Q-band of Ni-complexes is shifted to 650 nm. The Ni-porphyrin fused with two naphthalene units had bathochromically shifted Q-bands to 733 nm.
Conjugated polymers (CPs) based on diketopyrrolopyrrole (DPP) constitue an important class of high-performance organic semiconductors. While N-alkylation of DPP is required for the solution-based synthesis of DPP-based CPs, oxidative chemical...
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