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

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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.

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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All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Cite this

Fukuoka, T., Uchida, K., Sung, Y. M., Shin, J. Y., Ishida, S., Lim, J. M., 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, 53(6), 1506-1509. https://doi.org/10.1002/anie.201309921