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

ABSTRACT: Polycyclic aromatic hydrocarbons (PAHs) are interesting building blocks for the preparation of conjugated polymers due to their extended ? 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 sp3 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 sp3 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.

SUBMITTER: Lirette F

PROVIDER: S-EPMC6756517 | biostudies-literature | 2019 Sep

REPOSITORIES: biostudies-literature

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

Lirette Frédéric F Aumaitre Cyril C Fecteau Charles-Émile CÉ Johnson Paul A PA Morin Jean-François JF

ACS omega 20190905 12

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<sup>3</sup> carbon bridge. Three conjugated copolymers with fluorene, isoindigo, and bithiophe ...[more]

PMID: 31552312

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