Journal Article Facile one-pot access to π-conjugated polymers via sequential bromination/direct arylation polycondensation

Saito, Hitoshi  ,  Chen, Jieran  ,  Kuwabara, Junpei  ,  Yasuda, Takeshi  ,  Kanbara, Takaki

8 ( 19 )  , pp.3006 - 3012 , 2017-05 , Royal Society of Chemistry
The synthesis of π-conjugated polymers starting from unfunctionalized aromatic monomers via sequential bromination/direct arylation polycondensation was investigated. The developed protocol provides a step-economical access to the polymers in a one-pot fashion, without the need for prior preparation and purification of dibrominated aromatic monomers or organometallic monomers. Benzyltrimethylammonium tribromide was effective for the bromination of 10-(2-octyldodecyl)phenothiazine and 4,4′-didodecyl-2,2′-bithiophene, and the obtained dibrominated aromatic monomers were used for the subsequent direct arylation polycondensation without isolation and purification. The direct arylation polycondensation reaction yielded the corresponding donor–acceptor-type π-conjugated polymers in moderate to good yields. The sequential protocol was also applicable to the synthesis of poly(3-hexylthiophene-2,5-diyl) from 3-hexylthiophene. The obtained polymers served as semiconducting materials in organic light-emitting diodes and organic photovoltaics.

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