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

Angewandte Chemie
Kento UetaAtsuhiro Osuka

Abstract

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.

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Citations

Jul 13, 2017·The Journal of Organic Chemistry·Krushna Chandra SahooHarapriya Rath
Oct 31, 2018·Chemistry, an Asian Journal·Shota OoiAtsuhiro Osuka
Feb 15, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Kento UetaAtsuhiro Osuka
Apr 24, 2018·Monatshefte für chemie·Michael HaasWolfgang Schöfberger
Aug 8, 2021·Chemistry : a European Journal·Takayuki TanakaAtsuhiro Osuka

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