Issue 18, 2022

Conformationally restricted and three-dimensionally extended carbazole-incorporating expanded porphyrinoids

Abstract

Condensation of 3,6-(1-phenyl-1-(2-pyrroyl)methyl)carbazole with pentafluoroaldehyde and subsequent oxidation with DDQ gave a carbazole-incorporating octaphyrin(1.1.1.0.1.1.1.0) analogue, 7, which was shown to exist as two locked conformers 7a and 7b. Both conformers were isolated and handled individually. Heating of 7a and/or 7b in DMSO-d6 at 130 °C afforded a stationary mixture of 7a/7b = 1/10. On the other hand, similar octaphyrin analogues bearing a 1,8-dibromocarbazole unit 7-2Br and 7-4Br were isolated. These octaphyrin analogues were further decorated by Suzuki–Miyaura coupling with α,α′-diboryltripyrrane to furnish 9 and 10, respectively, as a rare example of a three-dimensionally (3D) extended expanded porphyrinoids. It was shown that the porphyrin-like tetrapyrrolic cavity of 9 and 10 served as an effective ligand to the CuII metal.

Graphical abstract: Conformationally restricted and three-dimensionally extended carbazole-incorporating expanded porphyrinoids

Supplementary files

Article information

Article type
Research Article
Submitted
23 May 2022
Accepted
18 Jun 2022
First published
20 Jun 2022

Org. Chem. Front., 2022,9, 4798-4802

Conformationally restricted and three-dimensionally extended carbazole-incorporating expanded porphyrinoids

F. Li, K. Wang, Y. Rao, L. Xu, A. Osuka and J. Song, Org. Chem. Front., 2022, 9, 4798 DOI: 10.1039/D2QO00834C

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