An Aza-Diels–Alder Route to Polyquinolines

Polyquinolines have been studied since the early 1970s due to their favorable chemical, optical, electrical, and mechanical properties. However, surprisingly few synthetic strategies have been developed for the preparation of these polymers. Herein, we demonstrate the application of the aza-Diels–Al...

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Bibliographic Details
Published inMacromolecules Vol. 48; no. 3; pp. 557 - 561
Main Authors Dibble, David J, Umerani, Mehran J, Mazaheripour, Amir, Park, Young S, Ziller, Joseph W, Gorodetsky, Alon A
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 10.02.2015
Amer Chemical Soc
Subjects
Physical Sciences
Polymer Science
Science & Technology
AROMATIC POLYQUINOLINES
QUINOLINE
CONJUGATED POLYMERS
ELECTRON-TRANSPORT MATERIALS
BIOLOGICAL-ACTIVITIES
COPOLYMERS
SPECTRA
FACILE
DERIVATIVES
ELECTROLUMINESCENCE
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Summary:Polyquinolines have been studied since the early 1970s due to their favorable chemical, optical, electrical, and mechanical properties. However, surprisingly few synthetic strategies have been developed for the preparation of these polymers. Herein, we demonstrate the application of the aza-Diels–Alder (Povarov) reaction for the synthesis of soluble polyquinolines from a bifunctional monomer. Our approach furnishes polyquinolines with a unique architecture and connectivity in only two synthetic steps from inexpensive, commercially available reagents. The reported strategy may therefore represent a welcome addition to the polymer chemist’s toolkit by providing ready access to a diverse library of polyquinoline-type materials.
ISSN:0024-9297
1520-5835
DOI:10.1021/ma5020726