Synthesis and characterization of meso-substituted A(2)B corroles with extended π-electronic structure

ABSTRACT: We report the chemical synthesis and characterization of the stable 5,15-bis(pentafluorophenyl)-10-(trimethylsilylethynyl)corrole which serves as a precursor for the subsequent in situ sila-Sonogashira-cross-coupling reaction and metalation with copper(II) acetate. Under ambient conditions and a common catalyst system the reaction with 1-iodopyrene occurred within five hours. Due to the direct conjugation of the 18π-electronic system of the corrole macrocycle over the alkynyl group to the pyrene moiety the optical transitions in the Soret (B-) band Q-band region are significantly altered. The copper corrole exhibited complex hyperfine and superhyperfine structure in the EPR spectrum. The assignment of the EPR spectrum reveals the existence of an axial [CuII-cor(∙+)] species. GRAPHICAL ABSTRACT: [Image: see text] ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (10.1007/s00706-017-2114-6) contains supplementary material, which is available to authorized users.