Synthesis of antiaromatic tetrabenzodithiaamethyrin-Reference-Cited by-同舟云学术

Synthesis of antiaromatic tetrabenzodithiaamethyrin

Published:2021-08-25 Issue:10n12 Volume:25 Page:1055-1063
ISSN:1088-4246
Container-title:Journal of Porphyrins and Phthalocyanines
language:en
Short-container-title:J. Porphyrins Phthalocyanines

Author:

Okujima Tetsuo¹²,Kozumi Ryohei¹,Mori Shigeki²³,Chino Yoshiaki⁴,Takase Masayoshi¹,Uno Hidemitsu¹,Kobayashi Nagao⁴

Affiliation:

1. Graduate School of Science and Engineering, Ehime University, Matsuyama 790-8577, Japan

2. Research Unit for Power Generation and Storage Materials, Ehime University, Matsuyama 790-8577, Japan

3. Advanced Research Support Center, Ehime University, Matsuyama 790-8577, Japan

4. Faculty of Textile Science and Technology, Shinshu University, Ueda 386-8567, Japan

Abstract

Bicyclo[2.2.2]octadiene(BCOD)-fused dithiaamethyrin 4 was synthesized via a “3+3” condensation method. Thermal conversion of the BCOD moieties afforded tetrabenzodithiaamethyrin 5. The highly planar structures of 4 and 5 were confirmed by X-ray diffraction studies. The 1H NMR, absorption and MCD spectra, together with TD-DFT calculations revealed that both BCOD-fused and [Formula: see text]-extended dithiaamethyrins have a 24[Formula: see text] antiaromatic character.

Funder

JSPS KAKENHI

Publisher

World Scientific Pub Co Pte Ltd

Subject

General Chemistry

Link

https://www.worldscientific.com/doi/pdf/10.1142/S1088424621500966

Reference13 articles.

1. Synthesis and Antiaromatic Properties of Highly Planar Dithiaamethyrin

2. An efficient synthesis of conjugation-expanded carba- and azuliporphyrins using a bicyclo[2.2.2]octadiene-fused tripyrrane

3. Nucleus-Independent Chemical Shifts (NICS) as an Aromaticity Criterion

4. An Antiaromatic Porphyrin Complex: Tetraphenylporphyrinato(silicon)(L)2 (L = THF or Pyridine)

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

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