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Furuyama T, Sato T, Kobayashi N. A Bottom-up Synthesis of Antiaromatic Expanded Phthalocyanines: Pentabenzotriazasmaragdyrins, i.e. Norcorroles of Superphthalocyanines. J Am Chem Soc. 2015;137(43):13788-91doi: 10.1021/jacs.5b09853.
Furuyama, T., Sato, T., & Kobayashi, N. (2015). A Bottom-up Synthesis of Antiaromatic Expanded Phthalocyanines: Pentabenzotriazasmaragdyrins, i.e. Norcorroles of Superphthalocyanines. Journal of the American Chemical Society, 137(43), 13788-91. https://doi.org/10.1021/jacs.5b09853
Furuyama, Taniyuki, et al. "A Bottom-up Synthesis of Antiaromatic Expanded Phthalocyanines: Pentabenzotriazasmaragdyrins, i.e. Norcorroles of Superphthalocyanines." Journal of the American Chemical Society vol. 137,43 (2015): 13788-91. doi: https://doi.org/10.1021/jacs.5b09853
Furuyama T, Sato T, Kobayashi N. A Bottom-up Synthesis of Antiaromatic Expanded Phthalocyanines: Pentabenzotriazasmaragdyrins, i.e. Norcorroles of Superphthalocyanines. J Am Chem Soc. 2015 Nov 04;137(43):13788-91. doi: 10.1021/jacs.5b09853. Epub 2015 Oct 21. PMID: 26471859.
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J Am Chem Soc. 2015 Nov 04;137(43):13788-91. doi: 10.1021/jacs.5b09853. Epub 2015 Oct 21.

A Bottom-up Synthesis of Antiaromatic Expanded Phthalocyanines: Pentabenzotriazasmaragdyrins, i.e. Norcorroles of Superphthalocyanines.

Journal of the American Chemical Society

Taniyuki Furuyama, Takehito Sato, Nagao Kobayashi

Affiliations

  1. Department of Chemistry, Graduate School of Science, Tohoku University , Sendai 980-8578, Japan.

PMID: 26471859 DOI: 10.1021/jacs.5b09853

Abstract

The first example of an antiaromatic expanded phthalocyanine, classified as a norcorrole of a superphthalocyanine has been prepared and fully characterized. The newly developed phthalonitrile dimerization reaction was a crucial step, which allowed for the bottom-up synthesis of expanded phthalocyanines. Their structure was confirmed by single crystal X-ray diffraction analysis. The 20 π antiaromaticity of the macrocycles was suggested by optical and theoretical calculations.

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