A Bench-Stable Antiaromatic Porphyrinoid Complex

Ni(II) meso-dimesitylnorcorrole (1) is a 16π-electron antiaromatic porphyrinoid complex reported by Shinokubo et al. in 2012.¹⁾ Unlike many other antiaromatic compounds, 1 is a bench-stable compound. It has been demonstrated that 1 is a promising candidate as an electrode active material for rechargeable batteries, because of its reversible two-electron oxidation and two-electron reduction giving its aromatic dicationic and dianionic species, respectively.²⁾ Moreover, there is an increased interest in exploring properties of not only 1 but also its related compounds, such as the synthesis of pyridine-fused bis(norcorrole) derivatives using 1 as a starting material and the observation of their enhanced paratropic currents,³⁾ and the expression of aromaticity in a cyclophane composed of stacked Ni(II) norcorrole units.⁴⁾

Related Products

N1236

Ni(II) meso-Dimesitylnorcorrole

Related Product Category Pages

• Phthalocyanine Dyes, Porphyrin Dyes
• Phthalocyanine Complexes, Porphyrin Complexes [Magnetic Metal Complexes]

References

• 1) Gram-Scale Synthesis of Nickel(II) Norcorrole: The Smallest Antiaromatic Porphyrinoid
  • T. Ito, Y. Hayashi, S. Shimizu, J.-Y. Shin, N. Kobayashi, H. Shinokubo, Angew. Chem. Int. Ed. 2012, 51, 8542.
• 2) An Antiaromatic Electrode-Active Material Enabling High Capacity and Stable Performance of Rechargeable Batteries
  • J.-Y. Shin, T. Yamada, H. Yoshikawa, K. Awaga, H. Shinokubo, Angew. Chem. Int. Ed. 2014, 53, 3096.
• 3) Pyridine-Fused Bis(Norcorrole) through Hantzsch-Type Cyclization: Enhancement of Antiaromaticity by an Aromatic Bridge
  • X. Li, Y. Meng, P. Yi, M. Stępień, P. J. Chmielewski, Angew. Chem. Int. Ed. 2017, 56, 10810.
• 4) Three-dimensional aromaticity in an antiaromatic cyclophane
  • R. Nozawa, J. Kim, J. Oh, A. Lamping, Y. Wang, S. Shimizu, I. Hisaki, T. Kowalczyk, H. Fliegl, D. Kim, H. Shinokubo, Nat. Commun. 2019, 10, 3576.

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