Synthesis and properties of fluorinated polyimides with multi-bulky pendant groups

Wang, Chenyi; Cao, Shijie; Chen, Wentao; Xu, Chang; Zhao, Xiaoyan; Li, Jian; Ren, Qiang

doi:10.1039/c7ra01568b

Cited by 41 publications

(18 citation statements)

References 25 publications

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“…Among these, the polyimides synthesized from 6FDA ( P1C1 , P1C2 , and P1C3 ) have shown better solubility even in THF and acetone. This is due to the presence of hexafluoroisopropylidene moiety in the backbone of polyimide, which greatly suppresses the intermolecular interaction and thereby enhances the solubility even with the solvents like THF and acetone . Owing to their excellent solubility, these polyimides offer good processability, and hence, one can prepare the optical quality thin films from their corresponding solutions for device applications.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of chromophores and polyimides with a green chemistry approach for second‐order nonlinear optical applications

Doddamani

Tasaganva²,

Inamdar

2018

Polymers for Advanced Techs

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This article presents the synthesis of nonlinear optical responsive chromophores by adopting a green chemistry approach by coupling N‐methyl‐N‐(2‐hydroxyethyl)‐4‐amino benzaldehyde with barbituric acid, 1,3‐indanedione, and 1,3‐diethyl‐2‐thiobarbituric acid as the acceptors through stilbene linkage. We performed the synthesis in less than 10 minutes at room temperature with water as a solvent without catalyst. Two different side‐chain polyimides were synthesized from poly(hydroxy‐imide)s with chromophores by Mitsunobu reaction. The chromophores were characterized by Fourier transform infrared, 1H NMR, 13C NMR, and elemental analysis. However, the polyimides were characterized by Fourier transform infrared and 1H NMR. The inherent viscosities (ηinh) of polyimides were determined by Ubbelohde viscometer, which ranged between 0.1793 and 0.1890 dL/g. The molecular weights of the polyimides were determined using gel permeation chromatography and were in range of 23 000 to 26 000. Polyimides demonstrated an excellent solubility in polar aprotic solvents, indicating good processability. Thermal behavior of these polyimides was studied by differential scanning calorimetry and thermogravimetric analysis. The Tg's were in the range of 185°C to 255°C. The change in the molecular orientation in the polymer films after electrical poling was ascertained using ultraviolet‐visible spectrophotometer and atomic force microscopy. The thicknesses and refractive indices of the thin films were determined by an ellipsometer. The second harmonic generation coefficients of the corona‐poled polymer films at Topt's, determined by the Maker fringe technique, ranged between 59.33 and 77.82 pm/V. High thermal endurance observed for the polyimides is attributed to the extensive hydrogen bonds in the matrix. The developed polyimides showed no decay in second harmonic generation signals below 110°C, indicating the acceptance for nonlinear optical devices.

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Section: Resultsmentioning

confidence: 99%

Synthesis of chromophores and polyimides with a green chemistry approach for second‐order nonlinear optical applications

Doddamani

Tasaganva²,

Inamdar

2018

Polymers for Advanced Techs

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“…A diamine monomer, 2,2 ′ ‐bis[3,5‐di(4‐trifluoromethylphenyl)‐4‐(4‐aminophenoxy)phenyl]‐ sulfone (3) was synthesized by a three‐step reaction using 4,4 ′ ‐difluorodiphenyl sulfone and N ‐bromosuccinimide (NBS) as the starting materials ( Scheme ) . The key step involved the synthesis of bifluoro intermediate compound 2 by Suzuki coupling reaction of 1 with 4‐(trifluoromethyl)benzeneboronic acid.…”

Section: Recent Design Approaches To Prepare Cpismentioning

confidence: 99%

Section: Recent Design Approaches To Prepare Cpismentioning

confidence: 99%

Recent Trends on Transparent Colorless Polyimides with Balanced Thermal and Optical Properties: Design and Synthesis

Tapaswi

2019

Macro Chemistry & Physics

166

155

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Recently, colorless and transparent plastic substrates with high glass transition temperature and suitable thermo‐mechanical properties are in high demand in optoelectronic device industries, due to their various optical applications. Colorless polyimides (CPIs) exhibit both high thermo‐mechanical stability as well as high transparency that are suitable for optoelectronic applications. The most recent (2010–2018) developments on CPIs, in terms of design and synthesis of new monomers and their effects on the thermo‐optical properties of the obtained CPIs, are reviewed in this article.

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“…With the increase of the ratio of 6FDA to BPDA, the transmittance of the films increased from 14.44% to 69.28%, and had a significant increase, which was five times higher than that of the original one. The reason for this phenomenon was that the steric hindrance effect of the bis-trifluoromethyl group in the dianhydride causes the conformation of the molecular chain to be distorted and the stacking of the molecular chains to be loose, which could effectively weaken the intermolecular forces caused by the accumulation of molecular chains [27,28] . Therefore, the transmittance of the polyimide film has been significantly improved.…”

Section: Optical Properties Of Fluorinated Polyimide Filmsmentioning

confidence: 99%

Synthesis and properties of fluorinated copolymerized polyimide films

Cao

Liu

et al. 2020

Polímeros

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Two series of fluorinated copolymerized polyimide films with different dianhydride ratios were prepared via the conventional two-step method by using 4,4-oxydianiline(ODA) as the diamine monomer, 4,4'-(hexafluoroisopropylidene) diphthalic anhydride(6FDA), 4,4'-oxydiphthalic anhydride(ODPA) and 3,3',4,4'-biphenyl tetracarboxylic dianhydride(BPDA) as the dianhydride monomer in N, N-dimethylacetamide. With the increase of 6FDA in the proportion of dianhydride, the tensile strength of the polyimide film showed a decreasing trend. This work provided a high performance film. The mass retention rate at 800°C was above 50%. The glass transition temperatures of the two films were 260 °C and 275 °C. The storage modulus of the two were 1500 MPa and 1250 MPa. The loss modulus were 218.70 MPa and 120.74 MPa. The transmittance of the film was 71.43%. The transmittance of fluorinated copolymerized polyimide films were significantly improved in the visible region of ultraviolet light, indicating that the polyimide film with high transmittance, high tensile strength, high heat resistance and high storage modulus was successfully prepared. It had an excellent application prospect in the field of flexible display.

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Synthesis and properties of fluorinated polyimides with multi-bulky pendant groups

Abstract: A new family of fluorinated polyimides with four pendant trifluoromethylphenyl groups was prepared. The incorporation of multi-bulky pendant fluorinated groups and large noncoplanar structures brought about great improvement for their properties.

Cited by 41 publications

References 25 publications

Synthesis of chromophores and polyimides with a green chemistry approach for second‐order nonlinear optical applications

Synthesis of chromophores and polyimides with a green chemistry approach for second‐order nonlinear optical applications

Recent Trends on Transparent Colorless Polyimides with Balanced Thermal and Optical Properties: Design and Synthesis

Synthesis and properties of fluorinated copolymerized polyimide films

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