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Aromaticity Relocation in Perylene Derivatives upon Two-Electron Oxidation To Form Anthracene and Phenanthrene
- Source :
- Chemistry (Weinheim an der Bergstrasse, Germany). 22(41)
- Publication Year :
- 2016
-
Abstract
- We prepared perylene dications 1(2+) and 2(2+) by using "capped" perylene derivatives, and for the first time, successfully obtained single crystals of a perylene dication 1(2+) that enabled us to perform its structural analysis. We realized that the substituted aryl groups on perylene control the positions of positive charges, thus the remaining electronic system satisfies Clar's sextet rule toward the highest number of localized sextets. Experimental and theoretical evidence proved that Clar's aromatic π-sextet rule could be applied even for the dicationic perylenes in a very simple way.
- Subjects :
- Anthracene
bond length alternation
010405 organic chemistry
oxidation
Aryl
Organic Chemistry
Perylene derivatives
Aromaticity
General Chemistry
Electron
aromaticity
Phenanthrene
010402 general chemistry
Photochemistry
01 natural sciences
Catalysis
0104 chemical sciences
Dication
chemistry.chemical_compound
dication
chemistry
perylene
Perylene
Subjects
Details
- ISSN :
- 15213765
- Volume :
- 22
- Issue :
- 41
- Database :
- OpenAIRE
- Journal :
- Chemistry (Weinheim an der Bergstrasse, Germany)
- Accession number :
- edsair.doi.dedup.....cef065c889196aa7145c69035b80772e