Chain-Growth Polymerization of Unusual Anion-Radical Monomers Based on Naphthalene Diimide: A New Route to Well-Defined n-Type Conjugated Copolymers

Strongly electron-deficient (n-type) main-chain π-conjugated polymers are commonly prepared via well-established step-growth polycondensation protocols which enable limited control over polymerization. Here we demonstrate that activated Zn and electron-deficient brominated thiophene-naphthalene diim...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2011-12, Vol.133 (49), p.19966-19970
Main Authors: Senkovskyy, Volodymyr, Tkachov, Roman, Komber, Hartmut, Sommer, Michael, Heuken, Maria, Voit, Brigitte, Huck, Wilhelm T. S, Kataev, Vladislav, Petr, Andreas, Kiriy, Anton
Format: Article
Language:English
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Summary:Strongly electron-deficient (n-type) main-chain π-conjugated polymers are commonly prepared via well-established step-growth polycondensation protocols which enable limited control over polymerization. Here we demonstrate that activated Zn and electron-deficient brominated thiophene-naphthalene diimide oligomers form anion-radical complexes instead of conventional Zn–organic derivatives. These highly unusual zinc complexes undergo Ni-catalyzed chain-growth polymerization leading to n-type conjugated polymers with controlled molecular weight, relatively narrow polydispersities, and specific end-functions.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja208710x