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Synthesis and Properties of High Performance Functional Polyimides Containing Rigid Nonplanar Conjugated Fluorene Moieties

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Abstract

A diamine (WuFDA) containing vertical rigid non-planar conjugated fluorene moiety and low polarizability group (C―F) was designed and synthesized through three steps of reactions (halogenated reaction, Suzuki coupling reaction, and reduction reaction). Four kinds of high performance functional polyimides (WuFPI-6F, WuFPI-BP, WuFPI-BT, and WuFPI-PM) were thus prepared by the condensation polymerization of WuFDA with four commercial dianhydride 6FDA, BPDA, BTDA, and PMDA, respectively. The polyimides exhibited low dielectric constant, excellent thermal stability, outstanding solubility, good film-forming property, and mechanical properties. The dielectric constants of the polyimides were in the range of 2.28−2.88 (f = 104 Hz). The 5% weight-loss temperatures (Td5%) in nitrogen were in the range of 555−584 °C, and the glass transition temperatures (Tg) were in the range of 408−448 °C. The weight loss of WuFPI-BP maintaining at 450 and 500 °C for half an hour was only 0.33% and 1.26%, respectively. All the WuFPIs could be dissolved in almost all organic solvents, even chloroform. The tensile strength and tensile modulus of these films were in the ranges of 78.6−85.7 MPa and 3.1−3.2 GPa, respectively. In addition, the polyimides displayed light color with special fluorescent and resistive switching (ON-OFF) characteristics; the maximum fluorescence emission was observed at 422−424 nm in NMP solution and at 470−548 nm in film state. The memory devices with the configuration of indium tin oxide/WuFPIs/aluminum (ITO/WuFPIs/Al) exhibited distinct volatile memory characteristics of static random access memory (SRAM), with an ON/OFF current ratio of 105−106. These functional polyimides showed attractive potential applications in the field of high performance flexible polymer photoelectronic devices or polymer memory devices.

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Acknowledgments

The financial support by the National 973 Program of China (No. 2014CB643605), the National Natural Science Foundation of China (Nos. 51373204 and 51873239), the Science and Technology Project of Guangdong Province (Nos. 2015B090915003 and 2015B090913003), the China Postdoctoral Science Foundation (No. 2017M612801), the Leading Scientific, Technical and Innovation Talents of Guangdong Special Support Program (No. 2016TX03C295), and the Fundamental Research Funds for the Central Universities (No. 161gzd08) are gratefully acknowledged.

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  1. These authors contributed equally to this work.

Authors and Affiliations

  1. PCFM Lab, GD HPPC Lab, Guangdong Engineering Technology Research Centre for High-performance Organic and Polymer Photoelectric Functional Films, State Key Laboratory of Optoelectronic Materials and Technologies, School of Chemistry, Sun Yat-sen University, Guangzhou, 510275, China

    Yi-Wu Liu, Li-Shuang Tang, Lun-Jun Qu, Si-Wei Liu, Zhen-Guo Chi, Yi Zhang & Jia-Rui Xu

  2. Key Laboratory of Advanced Packaging Materials and Technology of Hunan Province, School of Packaging and Materials Engineering, Hunan University of Technology, Zhuzhou, 412007, China

    Yi-Wu Liu

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  1. Yi-Wu Liu
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Synthesis and Properties of High Performance Functional Polyimides Containing Rigid Nonplanar Conjugated Fluorene Moieties

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Liu, YW., Tang, LS., Qu, LJ. et al. Synthesis and Properties of High Performance Functional Polyimides Containing Rigid Nonplanar Conjugated Fluorene Moieties. Chin J Polym Sci 37, 416–427 (2019). https://doi.org/10.1007/s10118-019-2225-0

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