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Synthesis and characterization of meso-substituted A₂B corroles with extended ?-electronic structure.

ABSTRACT:

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 18?-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.

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SUBMITTER: Haas M

PROVIDER: S-EPMC5906495 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature

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Synthesis and characterization of meso-substituted A2B corroles with extended π-electronic structure.

Haas Michael M Gonglach Sabrina S Müllegger Stefan S Schöfberger Wolfgang W

Monatshefte fur chemie 20171129 4

<h4>Abstract</h4>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 gr ...[more]

PMID: 29681657

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