Issue 10, 2012

Polynorbornenes with pendant perylene diimides for organic electronic applications

Abstract

Perylene-3,4,9,10-tetracarboxylic diimides (PDI) have been linked to norbornene through either an imide or a “bay” position. These PDI-functionalised norbornenes are readily polymerised using a ruthenium ring-opening metathesis polymerisation (ROMP) initiator. In one case the polymerisation is shown to be well controlled with a linear dependence of molecular weight on the monomer/initiator ratio. For the polymers with PDI–norbornene linkages through the imide nitrogen, UV-vis spectroscopy suggests significant PDI aggregation both in dilute solution and the solid state, a powder X-ray diffraction peak attributable to π-stacking is seen, and weak n-channel field-effect transistor behavior (electron mobilities <5 × 10−5 cm2 V−1 s−1) was observed. In contrast, the “bay”-linked polymer shows essentially monomer-like UV-vis spectra in both solution and the solid state, no X-ray evidence for π-stacking, and no measurable transistor behaviour. The polymers were used as acceptors in bulk heterojunction solar cells in combination with poly(3-hexylthiophene): low power conversion efficiencies (≤0.38%) were obtained, largely due to low short-circuit currents, again with the “bay”-linked polymer giving the poorest performance.

Graphical abstract: Polynorbornenes with pendant perylene diimides for organic electronic applications

Supplementary files

Article information

Article type
Paper
Submitted
08 Jun 2012
Accepted
09 Aug 2012
First published
17 Aug 2012

Polym. Chem., 2012,3, 2996-3006

Polynorbornenes with pendant perylene diimides for organic electronic applications

C. Huang, W. J. Potscavage, S. P. Tiwari, S. Sutcu, S. Barlow, B. Kippelen and S. R. Marder, Polym. Chem., 2012, 3, 2996 DOI: 10.1039/C2PY20401K

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