Synthesis and properties of colorless copolyimides derived from 4,4′-diaminodiphenyl ether-based diamines with different substituents

Lian, Ruhe; Lei, Xingfeng; Xiao, Yanjie; Xue, Shuyu; Xiong, Guo; Zhang, Zixiang; Dong, Yusen; Zhang, Qiuyu

doi:10.1039/d1py00633a

Cited by 23 publications

(24 citation statements)

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“…Good transparency in the visible light region is a key property for optical applications . As is known to all, conventional aromatic PI films always present deep colorations as a result of the intra- and intermolecular charge–transfer complexes. , Figure shows the transmittance curves of the resulting PI films with a thickness of ca. 10 μm.…”

Section: Resultsmentioning

confidence: 95%

Highly Refractive Polyimides Derived from Efficient Catalyst-Free Thiol–Yne Click Polymerization

et al. 2021

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Polyimides (PIs), owing to their inherent high refractive index and excellent physical properties, are required in advanced optical applications. They are traditionally synthesized through conventional two-step polycondensation, followed by hightemperature or chemical imidization, inevitably increasing energy consumption, environmental pollution, and production duration. Herein, for the first time, we synthesized PIs consisting of vinylene sulfide linkages via an efficient catalyst-free thiol−yne click polymerization, which would be accomplished within 2 h at 25 °C by simply mixing the dithiols and bisimide-containing diynes in THF, affording PIs with tensile strength ranging from 106.3 to 114.9 MPa, glass transition temperature up to 238 °C, thermal decomposition temperature as high as 381 °C, and desirable solubility, so that it was easily cast from solution into tough films. Moreover, the BPADA-TBT PI film demonstrates good optical performance, with its refractive index exceeding 1.70 at 633 nm and transmittance above 81% at 450 nm, making it a potential candidate in advanced optical applications.

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Section: Resultsmentioning

confidence: 95%

Highly Refractive Polyimides Derived from Efficient Catalyst-Free Thiol–Yne Click Polymerization

et al. 2021

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“…14.9°-16.2°and 23.8°-25.8°, resulting in two d-spacings of ∼5.7 Å and ∼3.6 Å according to Bragg's law. As is welldocumented that, the major halo at 14.9°-16.2°is due to the main-chain segmental packing for most of the aromatic polymers, 45,48,[50][51][52][53] while the shoulder peak locating at 23.8°-25.8°is probably ascribed to the presence of π-π stacking interactions of aromatic rings. 51,[54][55][56][57][58] For XRD patterns of the polymers containing amide linkages, the diffraction peaks correlated with π-π stacking interactions are slightly stronger than that for PI-R3 where amide hydrogen bonding is absent, indicating that the amide hydrogen bonding interaction plays a positive role in enhancing the π-π stacking interactions within the PAI polymer backbone.…”

Section: Paper Polymer Chemistrymentioning

confidence: 82%

“…These bisimide diamine monomers were prepared by reacting four 4,4′-diaminodiphenyl ether (ODA)-based diamines with 4,4′hexafluoroisopropylidene diphthalic anhydride (6FDA) to form internal imide linkages according to previous reports with slight modifications. [45][46][47] Using 2,2-bis-(4-carboxyphenyl)-hexafluoropropane (6FBA) as the complementary dicarboxylic acid…”

Section: Resultsmentioning

confidence: 99%

“…2-Methyl-4,4′-diaminodiphenyl ether ( m -MODA ), 2-trifluoromethyl-4,4′-diaminodiphenyl ether ( m -3FODA ) and 3-methyl-4,4′-diaminodiphenyl ether ( o -MODA ) were synthesized according to our previous report. 45 4,4′-Diaminodiphenyl ether ( ODA , Changzhou Sunlight Fine Chemicals Co., China) and 4,4′-(hexafluoroisopropylidene)diphthalic anhydride ( 6FDA , Changzhou Sunlight Fine Chemicals Co., China) were purified by vacuum sublimation before use. N -Methylpyrrolidone (NMP, J&K Chemicals, China), N,N -dimethylacetamide (DMAc, J&K Chemicals, China) and N,N -dimethylformamide (DMF, J&K Chemicals, China) were purified by vacuum distillation and dehydrated with 4 Å molecular sieves prior to use.…”

Section: Methodsmentioning

confidence: 99%

“…from the ortho methyl group, which restricts single bond rotation and segmental mobility. 45 The tensile stress-strain curves given in Fig. 4a and Fig.…”

Section: Polymer Chemistry Papermentioning

confidence: 99%

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High temperature shape memory poly(amide-imide)s with strong mechanical robustness

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Colorless poly(amide‐imide) copolymers for flexible display applications

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et al. 2022

J of Applied Polymer Sci

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Colorless polyimide (CPI) films showed great potential for flexible display applications due to their unique combination of excellent optical transparency, and outstanding thermal and mechanical properties. Herein, a series of colorless poly(amide‐imide)s were prepared via a conventional two‐step method, using 1,2,3,4‐cyclobutanetetracarboxylic dianhydride (CBDA), 4,4′‐(hexafluoroisopropylidene)diphthalic anhydride (6FDA), 2,2′‐bis(trifluoromethyl)benzidine (TFMB), and 4,4′‐diaminobenzanilide (DABA) as the monomers. The thermal, mechanical, and optical properties of these copolymers were optimized by adjusting the molar ratios of these monomers. The amide linkages significantly improved the mechanical properties and dimensional stability of the resultant CPI films due to strong hydrogen bonding interactions. In particular, CPI‐f films with monomer compositions of TFMB (50 mol%), DABA (50 mol%), 6FDA (50 mol%), and CBDA (50 mol%) exhibited tensile strength of 177 MPa, modulus of 5.5 GPa, coefficient of thermal expansion value of 18 ppm K−1, and glass transition temperature of 394°C. Furthermore, the optical properties of these copolymers were well balanced due to the adoption of CBDA, which can suppress the formation of charge transfer complexes. Specifically, these CPI films displayed transmittance at 550 nm of >88%, b* values of <5.5, haze values of <1%. The aforementioned results revealed that copolymerization is an effective strategy to achieve CPIs with excellent comprehensive properties.

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Synthesis and properties of colorless copolyimides derived from 4,4′-diaminodiphenyl ether-based diamines with different substituents

Abstract: Colorless polyimide (PI) films with outstanding mechanical and thermal properties are highly demanded in flexible electronics. Herein three 4,4’-diaminodiphenyl ether (ODA)-based diamines with different substitutions (-CH3, -CF3) and substitution...

Cited by 23 publications

References 50 publications

Highly Refractive Polyimides Derived from Efficient Catalyst-Free Thiol–Yne Click Polymerization

Highly Refractive Polyimides Derived from Efficient Catalyst-Free Thiol–Yne Click Polymerization

High temperature shape memory poly(amide-imide)s with strong mechanical robustness

Colorless poly(amide‐imide) copolymers for flexible display applications

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