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Literature DB >> 22811074

Gram-scale synthesis of nickel(II) norcorrole: the smallest antiaromatic porphyrinoid.

Tomohiro Ito¹, Yosuke Hayashi, Soji Shimizu, Ji-Young Shin, Nagao Kobayashi, Hiroshi Shinokubo.

Abstract

Small is beautiful: A ring-contracted sister of porphyrin, norcorrole, has been synthesized efficiently as a stable molecule by a nickel-templated strategy. The norcorrole complex is stable but exhibits a distinct antiaromatic character according to the Hückel rule. Oxidation of the norcorrole complex provides an aromatic oxacorrole complex.

Entities: Chemical

Mesh：

Substances：

Year: 2012 PMID： 22811074 DOI： 10.1002/anie.201204395

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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Cited

8 in total

1. Stacked antiaromatic porphyrins.

Authors: Ryo Nozawa; Hiroko Tanaka; Won-Young Cha; Yongseok Hong; Ichiro Hisaki; Soji Shimizu; Ji-Young Shin; Tim Kowalczyk; Stephan Irle; Dongho Kim; Hiroshi Shinokubo
Journal: Nat Commun Date: 2016-11-30 Impact factor: 14.919

2. Norcorrole as a Delocalized, Antiaromatic System.

Authors: Jeanet Conradie; Cina Foroutan-Nejad; Abhik Ghosh
Journal: Sci Rep Date: 2019-03-19 Impact factor: 4.379

3. Gram-scale synthesis of porphycenes through acid-catalyzed oxidative macrocyclizations of E/Z-mixed 5,6-diaryldipyrroethenes.

Authors: Toshikazu Ono; Ning Xu; Daiki Koga; Toshihiro Ideo; Manabu Sugimoto; Yoshio Hisaeda
Journal: RSC Adv Date: 2018-11-26 Impact factor: 3.361

Gram-scale synthesis of nickel(II) norcorrole: the smallest antiaromatic porphyrinoid.

1. Stacked antiaromatic porphyrins.

2. Norcorrole as a Delocalized, Antiaromatic System.

3. Gram-scale synthesis of porphycenes through acid-catalyzed oxidative macrocyclizations of E/Z-mixed 5,6-diaryldipyrroethenes.

Review 4. Heterocorroles: corrole analogues containing heteroatom(s) in the core or at a meso-position.

5. Visualisation of Chemical Shielding Tensors (VIST) to Elucidate Aromaticity and Antiaromaticity.

6. Highly-conducting molecular circuits based on antiaromaticity.

7. Cationic nickel porphyrinoids with unexpected reactivity.

8. A Volumetric Analysis of the ¹H NMR Chemical Shielding in Supramolecular Systems.