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Issue 17, 2014
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Stabilizing cations in the backbones of conjugated polymers

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Abstract

We synthesized a cross-conjugated polymer containing ketones in the backbone and converted it to a linearly conjugated, cationic polyarylmethine via a process we call “spinless doping” to create a new class of materials, conjugated polyions. This process involves activating the ketones with a Lewis acid and converting them to trivalent cations via the nucleophilic addition of electron-rich aryl moieties. Spinless doping lowers the optical band gap from 3.26 to 1.55 eV while leaving the intrinsic semiconductor properties of the polymer intact. Electrochemical reduction (traditional doping) further decreases the predicted gap to 1.18 eV and introduces radicals to form positive polarons; here, n-doping produces a p-doped polymer in its metallic state. Treatment with a nucleophile (NaOMe) converts the cationic polymer to a neutral, non-conjugated state, allowing the band gap to be tuned chemically, post-polymerization. The synthesis of these materials is carried out entirely without the use of Sn or Pd and relies on scalable Friedel–Crafts chemistry.

Graphical abstract: Stabilizing cations in the backbones of conjugated polymers

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Publication details

The article was received on 08 Nov 2013, accepted on 14 Jan 2014 and first published on 16 Jan 2014


Article type: Paper
DOI: 10.1039/C3TC32204A
Citation: J. Mater. Chem. C, 2014,2, 3407-3415
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    Stabilizing cations in the backbones of conjugated polymers

    T. P. Voortman, H. D. de Gier, R. W. A. Havenith and R. C. Chiechi, J. Mater. Chem. C, 2014, 2, 3407
    DOI: 10.1039/C3TC32204A

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