Angewandte Chemie - International Edition
Angewandte Chemie - International Edition
4 years ago

meso-Cumulenic 2H-Corroles from meso-Ethynyl-3H-corroles

meso-Cumulenic 2H-Corroles from meso-Ethynyl-3H-corroles
Kento Ueta, Takayuki Tanaka, Atsuhiro Osuka, Shota Ooi, Koji Naoda
Alkynyl-substituted 3H-corrole 9 a was converted to [3]cumulenic 2H-corrole 10 a by treatment with trimethylsilyl chloride (TMSCl), and 1,3-butadiyne-bridged 3H-corrole dimer 11 b was transformed into [5]cumulene-bridged 2H-corrole dimer 12 b by oxidation with PbO2. Both 10 a and 12 b were metalated to form ZnII complexes 10 a-Zn and 12 b-Zn. The structures of 10 a-Zn and 12 b-Zn show planar conformations with bond-length alternations that are analogous to those of tetraaryl [n]cumulenes. The cumulenic corrole dimers 12 b and 12 b-Zn display large NIR absorption bands in the range of 700–1400 nm (maximum ϵ≈1.0×105 m−1 cm−1) owing to the effective π-conjugation between the two corrole units through the [5]cumulene bridge. A π-conjugated dumbbell: [5]Cumulene-bridged 2H-corrole dimers capable of accommodating ZnII ions are synthesized from the corresponding meso-alkynyl-substituted 3H-corroles (see scheme). Their structures are revealed by X-ray diffraction analysis and the bond-length alternations in the cumulene segments are slightly larger than in conventional [n]cumulenes.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201703139

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