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The effect of ring expansion in thienobenzo[b]indacenodithiophene polymers for organic field-effect transistors
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Chen, Hu, Wadsworth, Andrew, Ma, Chun, Nanni, Alice, Zhang, Weimin, Nikolka, Mark, Luci, Alexander M. T., Perdigao, Luis M. A., Thorley, Karl J., Cendra, Camila, Larson, Bryon, Rumbles, Garry, Anthopoulos, Thomas D., Salleo, Alberto, Costantini, Giovanni, Sirringhaus, Henning and McCulloch, Iain (2019) The effect of ring expansion in thienobenzo[b]indacenodithiophene polymers for organic field-effect transistors. Journal of the American Chemical Society, 141 (47). pp. 18806-18813. doi:10.1021/jacs.9b09367 ISSN 0002-7863.
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WRAP-effect-ring-expansion-thienobenzo[b]indacenodithiophene-polymers-organic-field-effect-transistors-Costantini-2019.pdf - Accepted Version - Requires a PDF viewer. Download (3244Kb) | Preview |
Official URL: http://dx.doi.org/10.1021/jacs.9b09367
Abstract
A fused donor, thienobenzo[b]indacenodithiophene (TBIDT), was designed and synthesized using a novel acid-promoted cas-cade ring closure strategy, and copolymerized with a benzothiadiazole (BT) monomer. The backbone of TBIDT is an expan-sion of the well-known indacenodithiophene (IDT) unit and was expected to enhance the charge carrier mobility, by improving backbone planarity and facilitating short-contacts between polymer chains. However, the optimized field-effect transistors demonstrated an average saturation hole mobility of 0.9 cm2 V−1s−1, lower than the performance of IDT-BT (~1.5 cm2 V−1s−1). Mobilities extracted from time-resolved microwave conductivity (TRMC) measurements were consistent with the trend in hole mobilities in OFET devices. Scanning Tunneling Microscopy (STM) measurements and computational modelling illustrated that TBIDT-BT exhibits a less ordered microstructure in comparison to IDT-BT. This reveals that a regular side chain pack-ing density, independent of conformational isomers, is critical to avoid local free volume due to irregular packing, which can host trapping impurities. DFT calculations indicated that TBIDT-BT, despite containing a larger, planar unit, showed less stabilization of planar backbone geometries, in comparison to IDT-BT. This is due to the reduced electrostatic stabilizing inter-actions between the peripheral thiophene of the fused core with the BT unit, resulting in a reduction of the barrier to rotation around the single bond. These insights provide a greater understanding of the general structure-property relationships required for semiconducting polymer repeat units to ensure optimal backbone planarization, as illustrated with IDT-type units, guiding the design of novel semiconducting polymers with extended fused backbones for high-performance field-effect transistors.
| Item Type: | Journal Article | ||||||||||||||||||||||||||||||
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| Subjects: | Q Science > QD Chemistry Q Science > QH Natural history |
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| Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||||||||||||||||||||||||||||
| Library of Congress Subject Headings (LCSH): | Copolymers , Scanning tunneling microscopy , Transistors, Conjugated polymers | ||||||||||||||||||||||||||||||
| Journal or Publication Title: | Journal of the American Chemical Society | ||||||||||||||||||||||||||||||
| Publisher: | American Chemical Society | ||||||||||||||||||||||||||||||
| ISSN: | 0002-7863 | ||||||||||||||||||||||||||||||
| Official Date: | 27 November 2019 | ||||||||||||||||||||||||||||||
| Dates: |
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| Volume: | 141 | ||||||||||||||||||||||||||||||
| Number: | 47 | ||||||||||||||||||||||||||||||
| Page Range: | pp. 18806-18813 | ||||||||||||||||||||||||||||||
| DOI: | 10.1021/jacs.9b09367 | ||||||||||||||||||||||||||||||
| Status: | Peer Reviewed | ||||||||||||||||||||||||||||||
| Publication Status: | Published | ||||||||||||||||||||||||||||||
| Reuse Statement (publisher, data, author rights): | This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of the American Chemical Society, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/jacs.9b09367 | ||||||||||||||||||||||||||||||
| Access rights to Published version: | Restricted or Subscription Access | ||||||||||||||||||||||||||||||
| Date of first compliant deposit: | 30 October 2019 | ||||||||||||||||||||||||||||||
| Date of first compliant Open Access: | 15 October 2020 | ||||||||||||||||||||||||||||||
| RIOXX Funder/Project Grant: |
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