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Synthesis of Pyrrole‐Based Poly(arylenevinylene)s via Co‐Catalyzed Hydroarylation of Alkynes
Author(s) -
Iwamori Ryota,
Sato Ryota,
Kuwabara Junpei,
Yasuda Takeshi,
Kanbara Takaki
Publication year - 2021
Publication title -
macromolecular rapid communications
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.348
H-Index - 154
eISSN - 1521-3927
pISSN - 1022-1336
DOI - 10.1002/marc.202100283
Subject(s) - regioselectivity , monomer , steric effects , catalysis , pyrrole , polymer chemistry , polymer , stoichiometry , chemistry , materials science , organic chemistry
Abstract Polyaddition via the Co‐catalyzed hydroarylation of 1‐(2‐pyrimidinyl)pyrrole with aromatic diynes affords poly(arylenevinylene)s under mild conditions. This reaction avoids production of stoichiometric amounts of by‐products. Although structural analysis of the obtained polymers reveals the presence of 1,1‐vinylidene unit, switching the counter anion of the Co catalyst and steric hindrance of the diyne monomers improves the regioselectivity of the polymers. When a catalyst with bulky counter anions is used for the reaction of less hindered diyne monomers, 1,2‐vinylene linkages are formed dominantly over 1,1‐vinylidene linkages (93:7). The effect of the regioselectivity of the polymer on the optical and semiconducting properties is also evaluated.