Literature DB >> 24615867

Diprotonated [28]hexaphyrins(1.1.1.1.1.1): triangular antiaromatic macrocycles.

Shin-ichiro Ishida1, Tomohiro Higashino, Shigeki Mori, Hirotaka Mori, Naoki Aratani, Takayuki Tanaka, Jong Min Lim, Dongho Kim, Atsuhiro Osuka.   

Abstract

Protonation of meso-aryl [28]hexaphyrins(1.1.1.1.1.1) triggered conformational changes. Whereas protonation with trifluoroacetic acid led to the formation of monoprotonated Möbius aromatic species, protonation with methanesulfonic acid led to the formation of diprotonated triangular antiaromatic species. A peripherally hexaphenylated [28]hexaphyrin was rationally designed and prepared to undergo diprotonation to favorably afford a triangular-shaped antiaromatic species.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Möbius aromaticity; antiaromaticity; hexaphyrin; protonation; triangular shape

Year:  2014        PMID: 24615867     DOI: 10.1002/anie.201400301

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


  3 in total

1.  Switchable π-electronic network of bis(α-oligothienyl)-substituted hexaphyrins between helical versus rectangular circuit.

Authors:  Juwon Oh; Hirotaka Mori; Young Mo Sung; Woojae Kim; Atsuhiro Osuka; Dongho Kim
Journal:  Chem Sci       Date:  2015-12-08       Impact factor: 9.825

2.  Reversible π-system switching of thiophene-fused thiahexaphyrins by solvent and oxidation/reduction.

Authors:  Tomohiro Higashino; Atsushi Kumagai; Shigeyoshi Sakaki; Hiroshi Imahori
Journal:  Chem Sci       Date:  2018-08-14       Impact factor: 9.825

3.  Structural investigations into a new polymorph of F4TCNQ: towards enhanced semiconductor properties.

Authors:  Natalie T Johnson; Michael R Probert; Paul G Waddell
Journal:  Acta Crystallogr C Struct Chem       Date:  2021-06-28       Impact factor: 1.172

  3 in total

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