Please use this identifier to cite or link to this item: https://doi.org/10.1002/anie.201915327
Title: Formation of Azulene-Embedded Nanographene: Naphthalene to Azulene Rearrangement During the Scholl Reaction
Authors: Han, Yi
Xue, Zibo
LI GUANGWU 
GU YANWEI 
NI YONG 
DONG SHAOQIANG 
CHI CHUNYAN 
Keywords: Science & Technology
Physical Sciences
Chemistry, Multidisciplinary
Chemistry
azulenes
nanostructures
reaction mechanisms
rearrangements
Scholl reaction
POLYCYCLIC AROMATIC-HYDROCARBONS
SKELETAL REARRANGEMENT
CARBON NANOTUBES
CYCLODEHYDROGENATION
ABSORPTION
OXIDATION
DEFECTS
ARENES
Issue Date: 7-Apr-2020
Publisher: WILEY-V C H VERLAG GMBH
Citation: Han, Yi, Xue, Zibo, LI GUANGWU, GU YANWEI, NI YONG, DONG SHAOQIANG, CHI CHUNYAN (2020-04-07). Formation of Azulene-Embedded Nanographene: Naphthalene to Azulene Rearrangement During the Scholl Reaction. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION. ScholarBank@NUS Repository. https://doi.org/10.1002/anie.201915327
Abstract: Incorporation of a non-hexagonal ring into a nanographene framework can lead to new electronic properties. During the attempted synthesis of naphthalene-bridged double [6]helicene and heptagon-containing nanographene by the Scholl reaction, an unexpected azulene-embedded nanographene and its triflyloxylated product were obtained, as confirmed by X-ray crystallographic analysis and 2D NMR spectroscopy. A 5/7/7/5 ring-fused substructure containing two formal azulene units is formed, but only one of them shows an azulene-like electronic structure. The formation of this unique structure is explained by arenium ion mediated 1,2-phenyl migration and a naphthalene to azulene rearrangement reaction according to an in-silico study. This report represents the first experimental example of the thermodynamically unfavorable naphthalene to azulene rearrangement and may lead to new azulene-based molecular materials.
Source Title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
URI: https://scholarbank.nus.edu.sg/handle/10635/167691
ISSN: 1433-7851
1521-3773
DOI: 10.1002/anie.201915327
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