Colorless Electrochromic/Electrofluorochromic Dual-Functional Triphenylamine-Based Polyimides: Effect of a Tetraphenylethylene-Based π-Bridge on optoelectronic properties

Yu, Tiechen; Théato, Patrick; Yao, Hongyan; Liu, Huiling; Di, Yizeng; Sun, Zhonghui; Guan, Shaokang

doi:10.1016/j.cej.2022.138441

Cited by 26 publications

(20 citation statements)

References 56 publications

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“…The different trends of the absorption peaks are due to the fact that the whole oxidation process is divided into two different steps like the literature. 34 At 0-1.0 V, TPA with a methoxy group is first oxidized and the absorption peaks at 488 nm, 516 nm, and NIR region change and begin to increase, and the color of the film turns reddish brown. Then, when the voltage is applied from 1.0 to 1.2 V, the two TPAs at the C9 position continue to be oxidized, and new absorption peaks are generated at 881 and 909 nm.…”

Section: Ec Propertiesmentioning

confidence: 99%

“…33 Guan reduced π-π stacking by tetraphenylethylene with four rotatable benzene rings, and the prepared PI can be applied to bifunctional materials. 34 Besides, non-planar structure, torsion group, large volume side group, etc., could be introduced into main chain for increasing the flexibility of polymer main chain or avoiding tight packing of polymer chains. [35][36][37] TPA, has a large propeller structure which can disrupt the dense packing of polymer chains.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Non‐planar polyimides with monomer containing four triphenylamines for near‐infrared electrochromism and TNP detection

Xia

Zhai

et al. 2023

J of Applied Polymer Sci

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By using triphenylamine (TPA) with a propeller structure connected to the planar fluorene unit as monomer, three novel polyimide (PI)s were prepared through chemical imidization of N,N′‐(9,9‐bis(4‐(diphenylamino) phenyl)‐9H‐fluorene‐2,7‐diyl)‐bis(N‐(4‐methoxyphenyl) benzene‐1,4‐diamine) (TPAF‐NH2) with three kinds of dianhydrides. The three dimensional configurations are designed to decrease molecular stacking rising from strong imide bond, and for faster ion transport in cavity of PIs. All the three PIs have good performance of electrochromic(EC) and sensor. With the voltage increasing from 0 to 1.2 V, the color of P2 film changes from original yellow to red to blue with the response time of only 2.3 s (colored time [tc]) and 2.8 s (bleached time [tb]). The coloring efficiency (CE) of P2 reaches 310 cm2 C−1, with optical contrast (ΔT) of 54%. Especially, the electroactivity of P3 does not decrease significantly after 6000 s cycle. Additionally, there are dual‐band in near‐infrared (NIR) area after the PI being oxidized. P1 with photoluminescence (PL) quantum efficiency (φPL) of 48% can detect trinitrophenol (TNP) effectively. The novel PIs have promising prospect in NIR EC and TNP detection devices.

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Section: Ec Propertiesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Non‐planar polyimides with monomer containing four triphenylamines for near‐infrared electrochromism and TNP detection

Xia

Zhai

et al. 2023

J of Applied Polymer Sci

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“…T. Yu et al prepared P8 polymers with varying degrees of freedom along the TPE polymer backbone [ 142 ]. The flexibility of the polymers affected the packing and the electrochemical robustness of the film.…”

Section: Electrofluorochromic Polymersmentioning

confidence: 99%

“…The fluorescence contrast ratio improved to 8 in an operating dual-display chromic device (Figure 19B). Materials that change both their color and photoemission intensity with an applied potential are termed dual-functional materials [ 142 , 149 , 154 ]. Their use as the active layer in devices results in dual-mode displays, with visually detectable color and photoemission changes with an applied potential [ 155 , 156 ].…”

Section: Electrofluorochromic Polymersmentioning

confidence: 99%

Survey of Recent Advances in Molecular Fluorophores, Unconjugated Polymers, and Emerging Functional Materials Designed for Electrofluorochromic Use

2023

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In this review, recent advances that exploit the intrinsic emission of organic materials for reversibly modulating their intensity with applied potential are surveyed. Key design strategies that have been adopted during the past five years for developing such electrofluorochromic materials are presented, focusing on molecular fluorophores that are coupled with redox-active moieties, intrinsically electroactive molecular fluorophores, and unconjugated emissive organic polymers. The structural effects, main challenges, and strides toward addressing the limitations of emerging fluorescent materials that are electrochemically responsive are surveyed, along with how these can be adapted for their use in electrofluorochromic devices.

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“…Wide-band-gap triphenylamine derivatives are a well-studied class of organic EC materials due to their high charge-carrier mobilities, low oxidation potentials, reversible redox properties, transparent-to-visible color switching with high optical contrast, thermal and electrochemical stability, and tunability of the EC properties via easy substitution. − In our earlier work, we adopted a donor−π–donor (D−π–D) design strategy for the design of cross-linkable EC molecules, with two diphenylamine donor groups bridged by a π core, such as fluorene and tetraphenylethylene, and two styrene moieties that can be cross-linked attached to the diphenylamine groups. , The π core in these derivatives influence the EC properties via differential electronic coupling of the donor units in the neutral and oxidized states. In the current design, we introduced N-substituted carbazole as the π core, and two and three styrene groups are attached to the diphenylamine and carbazole parts, which is shown to have a significant role in controlling the EC parameters in both film and device conditions (Chart ).…”

Section: Introductionmentioning

confidence: 99%

Effect of Hyper-Cross-Linking on the Electrochromic Device Properties of Cross-Linkable Carbazole–Diphenylamine Derivatives

Balakrishnan,

Venugopal,

Harikumar

et al. 2023

ACS Appl. Polym. Mater.

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Triphenylamine derivatives are promising organic electrochromic (EC) materials due to their easy synthesis, low oxidation potentials, high charge-carrier mobilities, electrochemical stability, coloration efficiency, and tunability of EC properties via substitution. Further, the cross-linking strategy provides an added advantage to the small-molecule-based EC devices in terms of better-quality EC films with enhanced EC properties. Herein, we discuss the EC properties of two carbazole−diphenylamine derivatives, C-Sty2 and C-Sty3, with two and three thermally cross-linkable styryl units, respectively, following a donor−π− donor (D−π−D) design, where both the carbazole moiety and cross-linking styrene groups modulate the photophysical and EC properties. Both styryl derivatives formed rigid, uniform, and transparent films with high solvent resistance and exhibited excellent thermal and electrochemical stability upon cross-linking. C-Sty3, with three cross-linkable styryl units, could form more extended cross-links, leading to hyper-cross-linked films with distinct, regular, and porous morphology compared to C-Sty2. Spectroelectrochemical studies of the films showed a color change from a transparent colorless state to an initial light-yellow color and then a final dark-blue color with a color contrast of 65% at 890 nm for C-Sty2 and 78% at 850 nm for C-Sty3. The hypercross-linked films of C-Sty3 demonstrated enhanced coloration efficiency (248 cm 2 /C), optical contrast, and open-circuit memory compared to C-Sty2. Electrochemical impedance spectroscopy analysis showed lower solution and charge-transfer resistances (R s and R ct , respectively) for hyper-cross-linked films of C-Sty3, indicating higher conductivity and ion diffusion compared to C-Sty2. Thus, a comparison of the EC properties of two polymers with the same electroactive groups reveals the significance of hyper-crosslinking in the EC properties of these cross-linked polymers. Furthermore, the EC properties of the hyper-cross-linked D−π−D derivative, C-Sty3, were compared to those of previously reported molecules, demonstrating the importance of highly branched conducting polymers for EC applications.

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Colorless Electrochromic/Electrofluorochromic Dual-Functional Triphenylamine-Based Polyimides: Effect of a Tetraphenylethylene-Based π-Bridge on optoelectronic properties

Cited by 26 publications

References 56 publications

Non‐planar polyimides with monomer containing four triphenylamines for near‐infrared electrochromism and TNP detection

Non‐planar polyimides with monomer containing four triphenylamines for near‐infrared electrochromism and TNP detection

Survey of Recent Advances in Molecular Fluorophores, Unconjugated Polymers, and Emerging Functional Materials Designed for Electrofluorochromic Use

Effect of Hyper-Cross-Linking on the Electrochromic Device Properties of Cross-Linkable Carbazole–Diphenylamine Derivatives

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