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Issue 4, 2017
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Side-chain modulation of dithienofluorene-based copolymers to achieve high field-effect mobilities

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Abstract

A ladder-type dithieno[3,2-b:6,7-b′]fluorene (DTF), where the central fluorene is fused with two outer thiophene rings at its 2,3- and 6,7-junctions, is developed. The pentacyclic DTF monomers were polymerized with dithienodiketopyrrolopyrrole (DPP) acceptors to afford three alternating donor–acceptor copolymers PDTFDPP16, PDTFDPP20, and PDTFDPP32 incorporating different aliphatic side chains (R1 group at DTF; R2 group at the DPP moieties). The side-chain variations in the polymers play a significant role in determining not only the intrinsic molecular properties but also the intermolecular packing. As evidenced by the 2-dimensional GIXS measurements, PDTFDPP16 with octyl (R1) and 2-ethylhexyl (R2) side chains tends to align in an edge-on π-stacking orientation, whereas PDTFDPP20 using 2-butyloctyl (R1) and 2-ethylhexyl (R2) adopts a predominately face-on orientation. PDTFDPP32 with the bulkiest 2-butyloctyl (R1) and 2-octyldodecyl (R2) side chains shows a less ordered amorphous character. The OFET device using PDTFDPP20 with a face-on orientation determined by GIXS measurements achieved a high hole-mobility of up to 5 cm2 V−1 s−1. The high rigidity and coplanarity of the DTF motifs play an important role in facilitating intramolecular 1-dimensional charge transport within the polymer backbones. The implementation of main-chain coplanarity and side-chain engineering strategies in this research provides in-depth insights into structure–property relationships for guiding development of high-mobility OFET polymers.

Graphical abstract: Side-chain modulation of dithienofluorene-based copolymers to achieve high field-effect mobilities

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Publication details

The article was received on 14 Sep 2016, accepted on 20 Jan 2017 and first published on 10 Feb 2017


Article type: Edge Article
DOI: 10.1039/C6SC04129A
Citation: Chem. Sci., 2017,8, 2942-2951
  • Open access: Creative Commons BY license
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    Side-chain modulation of dithienofluorene-based copolymers to achieve high field-effect mobilities

    C. Lee, Y. Lai, J. Hsu, P. Huang and Y. Cheng, Chem. Sci., 2017, 8, 2942
    DOI: 10.1039/C6SC04129A

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