Aryne Polymerization Enabling Straightforward Synthesis of Elusive Poly(ortho-arylene)s

Herein we present the first straightforward aryne polymerization that successively connects aromatic rings at their ortho-positions, directly giving poly­(ortho-phenylene)­s of up to ca. 100-mer size. The polymerization proceeds smoothly in a chain-growth fashion in the presence of a monovalent copp...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2015-01, Vol.137 (1), p.74-77
Main Authors: Mizukoshi, Yoshihide, Mikami, Koichiro, Uchiyama, Masanobu
Format: Article
Language:English
Subjects:
Hydrocarbons, Aromatic - chemical synthesis
Hydrocarbons, Aromatic - chemistry
Molecular Structure
Polymerization
Polymers - chemical synthesis
Polymers - chemistry
Quantum Theory
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Summary:Herein we present the first straightforward aryne polymerization that successively connects aromatic rings at their ortho-positions, directly giving poly­(ortho-phenylene)­s of up to ca. 100-mer size. The polymerization proceeds smoothly in a chain-growth fashion in the presence of a monovalent copper reagent. Direct synthesis of poly­(ortho-arylene)­s has been a “missing piece” of aromatic chemistry for a long time (although the discovery of arynes dates back to 1902), in contrast to the well-investigated para- and meta-linked polyarylenes. Our achievement reported here is expected to open up new areas of nanocarbon and materials science.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja5112207