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Issue 39, 2015
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Regioisomeric control of charge transport polarity for indigo-based polymers

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Abstract

In this work we report the opposite charge transport polarity observed for two regioisomeric polymer semiconductors. Previously, we observed n-type electron transport behaviour for a polymer semiconductor, 6,6′-PIDBDT, which contains 6,6′-indigo units. Electron distributions in the lowest unoccupied molecular orbital (LUMO) and the highest occupied molecular orbital (HOMO) of indigo calculated by density functional theory (DFT) could explain the electron transport behaviour since electrons can be delocalized along the polymer backbone through the LUMO rather than the HOMO via the 6- and 6′-positions. Serendipitously, we found that the 5- and 5′-positions of indigo are occupied by electrons in the HOMO but empty in the LUMO, opposite to the 6- and 6′-positions. This suggests that 5,5′-PIDBDT containing the 5,5′-indigo units, a regioisomer of 6,6′-PIDBDT, may exhibit the opposite p-type charge transport behaviour. To prove our assumption, we synthesized 5,5′-PIDBDT and found that this polymer indeed showed p-type semiconductor behaviour. Hence we demonstrated a novel approach to control the electron or hole charge transport polarity by simply varying the main chain regiochemical connections.

Graphical abstract: Regioisomeric control of charge transport polarity for indigo-based polymers

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Publication details

The article was received on 29 May 2015, accepted on 15 Aug 2015 and first published on 18 Aug 2015


Article type: Paper
DOI: 10.1039/C5PY00821B
Author version available: Download Author version (PDF)
Citation: Polym. Chem., 2015,6, 6998-7004
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    Regioisomeric control of charge transport polarity for indigo-based polymers

    C. Guo, J. Quinn, B. Sun and Y. Li, Polym. Chem., 2015, 6, 6998
    DOI: 10.1039/C5PY00821B

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