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Fluorinated Dithienylethene–Naphthalenediimide Copolymers for High-Mobility n-Channel Field-Effect Transistors

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Organic Solids Laboratory, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
University of Chinese Academy of Sciences, Beijing 100049, China
§ School of Material Science and Engineering, University of Science and Technology Beijing, Beijing 100083, China
*E-mail: [email protected] (W.Z.).
*E-mail: [email protected] (G.Y.).
Cite this: Macromolecules 2017, 50, 16, 6098–6107
Publication Date (Web):August 10, 2017
https://doi.org/10.1021/acs.macromol.7b01169
Copyright © 2017 American Chemical Society
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Abstract

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We develop two donor–acceptor copolymers based on a fluorinated dithienylethene building block, namely PNFDTE1 and PNFDTE2, in which naphthalenediimide (NDI) acts as an acceptor unit. Thermogravimetric analysis displayed both copolymers having good thermal stability with high decomposition temperatures over 400 °C. Broad absorption spectra were observed in the UV–vis–NIR region, with the absorption maxima being 720 and 724 nm for PNFDTE1 and PNFDTE2, respectively. Cyclic voltammetry tests exhibited deep-lying lowest unoccupied molecular orbital energy levels of ca. −4.0 eV. Two-dimensional grazing incidence X-ray diffraction patterns showed that different packing modes for two polymers result in the variation in charge transport properties. Backbone fluorination effectively decreases electron injection barrier, thereby facilitating electron mobility. An impressive electron mobility of 3.20 cm2 V–1 s–1 was achieved in air for PNFDTE1-based polymer field-effect transistors fabricated on the poly(ethylene terephthalate) substrate. The mobility value is almost the highest for NDI-containing polymers on the flexible substrate. This work provides a guideline for design and synthesis of fluorinated semiconductors that enables control of charge-transport polarity.

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The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.macromol.7b01169.

  • TGA curves of the polymers, temperature-dependent absorption spectra, CV, GIXRD data, NMR spectra, AFM images, and other device characteristics and data (PDF)

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