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Synthesis and Properties of Conjugated Polymers Based on a Ladderized Anthanthrene Unit

[Image: see text] Polycyclic aromatic hydrocarbons (PAHs) are interesting building blocks for the preparation of conjugated polymers due to their extended π surface and planar conformation. However, their use as comonomer in conjugated polymers often leads to nonplanar main chains as a consequence o...

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Detalles Bibliográficos
Autores principales: Lirette, Frédéric, Aumaitre, Cyril, Fecteau, Charles-Émile, Johnson, Paul A., Morin, Jean-François
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6756517/
https://www.ncbi.nlm.nih.gov/pubmed/31552312
http://dx.doi.org/10.1021/acsomega.9b01185
Descripción
Sumario:[Image: see text] Polycyclic aromatic hydrocarbons (PAHs) are interesting building blocks for the preparation of conjugated polymers due to their extended π surface and planar conformation. However, their use as comonomer in conjugated polymers often leads to nonplanar main chains as a consequence of high steric hindrance at the linking point. Herein, we report the synthesis of a ladderized anthanthrene unit using an sp(3) carbon bridge. Three conjugated copolymers with fluorene, isoindigo, and bithiophene derivatives have been synthesized and characterized to study the effect of such ladderization on the electronic properties. The dihedral angle between the ladderized anthanthrene and adjacent units has been significantly reduced by the formation of the sp(3) carbon bridge, thus eliminating the steric hindrance with the proton at the peri position of the anthanthrene unit and red-shifting the absorption spectrum by 25 nm.