Double Ring Expansion from an Aromatic [18]Porphyrin(1.1.1.1) to an Antiaromatic [20]Porphyrin(2.1.2.1)

The two-electron reduction of ad iprotonated dodecaphenylporphyrin derivative by Na 2 S 2 O 4 gave ac orresponding isophlorin (Iph)s electively.F ormation of Iph was confirmed by spectroscopic measurements and the isolation of tetramethylated Iph.F urther reduction of Iph proceeded to form an unprecedented four-electron-reduced porphyrin (IphH 2 ), whichw as fully characterized by spectroscopic and X-ray crystallographic analysis. IphH 2 ,w ith au nique conformation, could be oxidized to reproduce the starting porphyrin, resulting in ap roton-coupled four-electron reversible redoxsystem.Supportinginformation and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.

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Formation and Isolation of a Four‐Electron‐Reduced Porphyrin Derivative by Reduction of a Stable 20π Isophlorin

Suzuki

Kotani

Ishizuka

et al. 2018

Angewandte Chemie

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Boron(III) Carbazosubphthalocyanines: Core‐Expanded Antiaromatic Boron(III) Subphthalocyanine Analogues

et al. 2019

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Condensation of 1,8-diamino-3,6-dichlorocarbazole with aseries of disubstituted 1,3-diiminoisoindolines,followed by treatment with BF 3 ·OEt 2 led to the formation of the corresponding core-expanded boron(III) subphthalocyanine analogues.T hese air-stable p-conjugated boron(III) carbazosubphthalocyanines possess two boron-containing seven-membered-ring units and a16p-electron skeleton, and represent the first examples of antiaromatic boron(III) subphthalocyanine analogues as supported by spectroscopic and theoretical studies.T he molecular structure of one of these compounds was unambiguously determined by single-crystal X-ray diffraction analysis.I nc ontrast to typical boron(III) subphthalocyanines,whichadopt acone-shaped structure,the p skeleton of this compound is almost planar.

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Low‐Valent Zirconocene‐Mediated Synthesis of Porphyrin(2.1.2.1)s and Its Extension to Synthesis of a Porphyrin(2.1.2.1) Nanobarrel

Song

Zhao

et al. 2022

Angewandte Chemie

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Rosenthal's‐reagent‐mediated intramolecular cyclometallation of α,α‐dialkynyldipyrrin nickel(II) complex and subsequent acid treatment afforded a 1,3‐butadiene‐embedded porphyrin(2.1.2.1), 6, which served as a reactive diene towards dienophiles such as dimethyl acetylenedicarboxylate (DMAD) and benzyne to give corresponding Diels–Alder adducts. Diels–Alder reaction of 6 and benzdiyne gave adducts 14, 15 a, and 15 b along with a trace amount of porphyrin(2.1.2.1) barrel 13. Stepwise routes using 14 or 15 a/15 b as a substrate allowed for the synthesis of 13 as a single stereoisomer. The nanobarrel structure for 13 was revealed by X‐ray diffraction, where its cavity held two chloroform molecules via C−H⋅⋅⋅π interaction. DFT calculations revealed that the electrostatic attraction was dominant with binding energy of 32.8 kcal mol−1.

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Double Ring Expansion from an Aromatic [18]Porphyrin(1.1.1.1) to an Antiaromatic [20]Porphyrin(2.1.2.1)

Cited by 12 publications

References 65 publications

Formation and Isolation of a Four‐Electron‐Reduced Porphyrin Derivative by Reduction of a Stable 20π Isophlorin

Formation and Isolation of a Four‐Electron‐Reduced Porphyrin Derivative by Reduction of a Stable 20π Isophlorin

Boron(III) Carbazosubphthalocyanines: Core‐Expanded Antiaromatic Boron(III) Subphthalocyanine Analogues

Low‐Valent Zirconocene‐Mediated Synthesis of Porphyrin(2.1.2.1)s and Its Extension to Synthesis of a Porphyrin(2.1.2.1) Nanobarrel

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