A Synthesis of Peripherally Annulated Phenanthroporphyrins

Novel synthesis of unusual phenanthrene-fused porphyrins was achieved by the stepwise precursor method. C4h symmetrical octaaryltetrabenzoporphyrin (octaarylTBPs) was synthesized via cyclotetramerization and thermal conversion based on retro Diels–Alder reaction. The oxidative intramolecular cyclization of octaarylTBPs afforded tri- and tetraphenanthroporphyrins.

Prof. Okujima, in collaboration with Prof. Kobayashi at Shinshu University, reported the synthesis, molecular structure, optical properties and electronic structure of unusual phenanthrene-fused porphyrins.
Precursor porphyrins fused with aryl-substituted bicyclo[2.2.2]octadiene afforded the corresponding arylbenzoporphyrins (arylBPs) by retro Diels–Alder reaction. Unusual phenanthroporphyrins were obtained via the intramolecular Scholl reaction of arylBPs. We analyzed the optical and electronic structures using magnetic circular dichroism spectroscopy and time-dependent density functional theory calculations.
Our findings were published on April 25, 2023 in Organic Letters.

Reference URL: https://pubs.acs.org/doi/10.1021/acs.orglett.3c00876

Bibliographic Information

Synthesis of Peripherally Annulated Phenanthroporphyrins
Muramatsu, Kota; Okujima, Tetsuo*; Mori, Shigeki; Kikuchi, Shion; Ando, Shimpei; Okada, Yusuke; Takase, Masayoshi; Uno, Hidemitsu; Kobayashi, Nagao*
Org. Lett. 2023, 25 (17), 3049-3054.
American Chemical Society
DOI: 10.1021/acs.orglett.3c00876 (2023.4.25)

Fundings

• Japan Society for the Promotion of Science（22K05082）

Media

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  Stepwise synthesis of unusual phenanthrene-fused porphyrins

  Stepwise synthesis of unusual phenanthrene-fused porphyrins

  credit : Tetsuo OKUJIMA ，Ehime University
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