Beilstein J. Org. Chem.2025,21, 1272–1305, doi:10.3762/bjoc.21.99
of the azulene moiety are the most electron-rich, and pristine azulene is known to form 1,3-polyazulene upon oxidation [67], which may hinder the formation of the desired fused products. For instance, Itami and co-workers [68] reported that the oxidation of compound 92 resulted in the expected fully
-dibromoazulene (203) was annealed on an Au(111) surface, leading to the formation of 2,6-polyazulene chains 204. Upon heating these chains to 730 K, laterally fused chains were observed. The distinctive phagraphene nanoribbon 205 and the THP-graphene nanoribbon 206 were formed. This transformation provides solid
PDF
Graphical Abstract
Figure 1:
a) Stone–Wales (red) and azulene (blue) defects in graphene; b) azulene and its selected resonance ...
Beilstein J. Org. Chem.2021,17, 2164–2185, doi:10.3762/bjoc.17.139
-containing homo- and copolymers, including brief descriptions of their key properties.
Keywords: azulene; chemical synthesis; copolymer; non-alternant hydrocarbon; organic electronics; polyazulene; Introduction
Azulene (C10H8) is a non-alternant, non-benzenoid, 10 π electron aromatic hydrocarbon containing
synthesis of azulene-containing homo- and copolymers that have been achieved during the last three decades.
Review
Azulene-containing homopolymers
The polyazulenes
The earliest chemical synthesis of polyazulene was reported by Neoh, Kang, and Tan in 1988 [18]. Their strategy was based on the oxidative
polymerization of azulene (1) by iodine or bromine to obtain polyazulene–iodine/bromine complexes (PAz-I2/PAz-Br2) (Scheme 1).
The PAZ-I2 complex was found to be insoluble whereas PAZ-Br2 was sparingly soluble in most of the organic solvents. Although no structure was proposed for these polymer complexes, based
PDF
Graphical Abstract
Figure 1:
Chemical structure, numbering scheme, and resonance form of azulene.