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Effective Synthesis of Ladder-type Oligo(p-aniline)s and Poly(p-aniline)s via Intramolecular SNAr Reaction.

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Symmetric ladder-type oligo(p-aniline)s and poly(p-aniline)s were successfully synthesized by an intramolecular ring closure in a highly efficient SNAr reaction from oligo(p-phenylene)s and poly(p-phenylene)s with fluorine (F) and secondary amine (NH)… Click to show full abstract

Symmetric ladder-type oligo(p-aniline)s and poly(p-aniline)s were successfully synthesized by an intramolecular ring closure in a highly efficient SNAr reaction from oligo(p-phenylene)s and poly(p-phenylene)s with fluorine (F) and secondary amine (NH) groups. Unlike Cadogan ring closure, the newly designed cyclization reaction will not produce a mixture of symmetric and nonsymmetric structures. Moreover, the introduction of the F atom does not hinder Suzuki polymerization. The result indicates that preparing regular oligomers and polymers with a nitrogen bridge is possible.

Keywords: aniline; type oligo; aniline poly; reaction; ladder type; oligo aniline

Journal Title: Organic letters
Year Published: 2021

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