Thienylmethylene Oxindole Based Conjugated Polymers via Direct Arylation Polymerization and Their Electrochromic Propert
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ARTICLE
POLYMER SCIENCE
https://doi.org/10.1007/s10118-021-2503-5 Chinese J. Polym. Sci.
Thienylmethylene Oxindole Based Conjugated Polymers via Direct Arylation Polymerization and Their Electrochromic Properties Wei Yanga, Hao-Guo Yuec, Dong Zhaoa, Hui Yanc, Kang-Li Caob*, Jin-Sheng Zhaoc*, and Qing Zhanga* a Shanghai Key Laboratory of Electrical Insulation and Thermal Aging, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai
200240, China b Shanghai Space Environment Simulation and Verification Engineering Technology Research Center, Shanghai Institute of Spacecraft Equipment, Shanghai 200240, China c College of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng 252059, China
Electronic Supplementary Information Abstract Direct arylation methods have been used to polymerize thienylmethylene oxindoles (TEIs) and 3,3-bis[[(2-ethylhexyl)oxy]methyl]-3,4dihydro-2H-thieno-[3,4-b][1,4]dioxepin (ProDOT) for new donor-acceptor conjugated polymers. The polymers exhibited blue hues in neutralstate with distinct color-to-transmissive reversible electrochromic switching under applied potentials from 0 V to +1.5 V, and showed high coloration efficiencies (436−438 cm2·C−1) in near-infrared regions with high switching speeds around 1−2 s under ambient conditions. Keywords Electrochromic; Direct arylation; Donor-acceptor polymers; Isoindigo; Near-infrared Citation: Yang, W.; Yue, H. G.; Zhao, D.; Yan, H.; Cao, K. L.; Zhao, J. S.; Zhang, Q. Thienylmethylene oxindole based conjugated polymers via direct arylation polymerization and their electrochromic properties. Chinese J. Polym. Sci. https://doi.org/10.1007/s10118-021-2503-5
INTRODUCTION Conjugated polymers are considered promising materials for electronic and optoelectronic applications including thin-film transistors,[1−3] solar cells[4−6] and electrochromics.[7−15] They are conventionally synthesized by transition metal-catalyzed crosscoupling reactions, such as Stille and Suzuki reactions.[16,17] The research on direct arylation polymerization for conjugated polymers started about ten years ago.[18,19] Recently, palladiumcatalyzed direct arylation reactions have become increasingly important routes for the syntheses of conjugated polymers, because the air, moisture and functional group sensitive metalation steps in the monomer preparation can be bypassed.[19−21] The approach also expends the scope of building blocks and avoids stoichiometric organometallic waste. Electrochromism refers to the phenomena that materials change their color upon the applying of a voltage across them.[22] Electrochromic devices have many important applications, such as smart windows and electronic paper for fulfilling both visual comfort and energy-efficiency.[23,24] The donoracceptor approach has been applied in electrochromic polymers for fine-tuning the highest occupied molecular orbital/
* Corresponding authors, E-mail: [email protected] (K.L.C.) E-mail: [email protected] (J.S.Z.) E-mail: [email protected] (Q.Z.) Received
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