Near-IR absorbing nickel(II) porphyrinoids prepared by regioselective insertion of silylenes into antiaromatic nickel(II) norcorrole

Takaki Fukuoka, Kenya Uchida, Young Mo Sung, Ji Young Shin, Shintaro Ishida, Jong Min Lim, Satoru Hiroto, Ko Furukawa, Dongho Kim, Takeaki Iwamoto, Hiroshi Shinokubo

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

The treatment of an antiaromatic norcorrole NiII complex with a kinetically stabilized silylene provided ring-expansion products in excellent yields through the highly regio- and stereoselective insertion into the β-β pyrrolic C-C bonds. The resultant NiII porphyrinoid monoinsertion product exhibited relatively strong near-IR absorption bands due to the small HOMO-LUMO gap in spite of the disrupted cyclic π-conjugation by the silicon atom. This looks like a good spot for Si: The treatment of an antiaromatic norcorrole NiII complex with a kinetically stabilized silylene provided ring-expansion products in excellent yields by highly regioselective insertion into the β-β pyrrolic C-C bonds. The absorption spectrum of the resulting silicon-containing NiII porphyrinoid is substantially red-shifted into the near-infrared region.

Original languageEnglish
Pages (from-to)1506-1509
Number of pages4
JournalAngewandte Chemie - International Edition
Volume53
Issue number6
DOIs
Publication statusPublished - 2014 Feb 3

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Silicon
Nickel
Absorption spectra
Infrared radiation
Atoms

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Cite this

Fukuoka, Takaki ; Uchida, Kenya ; Sung, Young Mo ; Shin, Ji Young ; Ishida, Shintaro ; Lim, Jong Min ; Hiroto, Satoru ; Furukawa, Ko ; Kim, Dongho ; Iwamoto, Takeaki ; Shinokubo, Hiroshi. / Near-IR absorbing nickel(II) porphyrinoids prepared by regioselective insertion of silylenes into antiaromatic nickel(II) norcorrole. In: Angewandte Chemie - International Edition. 2014 ; Vol. 53, No. 6. pp. 1506-1509.
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abstract = "The treatment of an antiaromatic norcorrole NiII complex with a kinetically stabilized silylene provided ring-expansion products in excellent yields through the highly regio- and stereoselective insertion into the β-β pyrrolic C-C bonds. The resultant NiII porphyrinoid monoinsertion product exhibited relatively strong near-IR absorption bands due to the small HOMO-LUMO gap in spite of the disrupted cyclic π-conjugation by the silicon atom. This looks like a good spot for Si: The treatment of an antiaromatic norcorrole NiII complex with a kinetically stabilized silylene provided ring-expansion products in excellent yields by highly regioselective insertion into the β-β pyrrolic C-C bonds. The absorption spectrum of the resulting silicon-containing NiII porphyrinoid is substantially red-shifted into the near-infrared region.",
author = "Takaki Fukuoka and Kenya Uchida and Sung, {Young Mo} and Shin, {Ji Young} and Shintaro Ishida and Lim, {Jong Min} and Satoru Hiroto and Ko Furukawa and Dongho Kim and Takeaki Iwamoto and Hiroshi Shinokubo",
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Fukuoka, T, Uchida, K, Sung, YM, Shin, JY, Ishida, S, Lim, JM, Hiroto, S, Furukawa, K, Kim, D, Iwamoto, T & Shinokubo, H 2014, 'Near-IR absorbing nickel(II) porphyrinoids prepared by regioselective insertion of silylenes into antiaromatic nickel(II) norcorrole', Angewandte Chemie - International Edition, vol. 53, no. 6, pp. 1506-1509. https://doi.org/10.1002/anie.201309921

Near-IR absorbing nickel(II) porphyrinoids prepared by regioselective insertion of silylenes into antiaromatic nickel(II) norcorrole. / Fukuoka, Takaki; Uchida, Kenya; Sung, Young Mo; Shin, Ji Young; Ishida, Shintaro; Lim, Jong Min; Hiroto, Satoru; Furukawa, Ko; Kim, Dongho; Iwamoto, Takeaki; Shinokubo, Hiroshi.

In: Angewandte Chemie - International Edition, Vol. 53, No. 6, 03.02.2014, p. 1506-1509.

Research output: Contribution to journalArticle

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AU - Sung, Young Mo

AU - Shin, Ji Young

AU - Ishida, Shintaro

AU - Lim, Jong Min

AU - Hiroto, Satoru

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AU - Iwamoto, Takeaki

AU - Shinokubo, Hiroshi

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AB - The treatment of an antiaromatic norcorrole NiII complex with a kinetically stabilized silylene provided ring-expansion products in excellent yields through the highly regio- and stereoselective insertion into the β-β pyrrolic C-C bonds. The resultant NiII porphyrinoid monoinsertion product exhibited relatively strong near-IR absorption bands due to the small HOMO-LUMO gap in spite of the disrupted cyclic π-conjugation by the silicon atom. This looks like a good spot for Si: The treatment of an antiaromatic norcorrole NiII complex with a kinetically stabilized silylene provided ring-expansion products in excellent yields by highly regioselective insertion into the β-β pyrrolic C-C bonds. The absorption spectrum of the resulting silicon-containing NiII porphyrinoid is substantially red-shifted into the near-infrared region.

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