Highly refractive polyimides containing pyridine and sulfur units: synthesis and thermal, mechanical, solubility and optical properties

Guan, Yue; Dong, Weibing; Che, Wang; Shang, Dejing

doi:10.1002/pi.5359

Cited by 10 publications

(5 citation statements)

References 31 publications

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“…That may be because that carbonyl group adjacent to the aromatic ring could be further decomposed to carbon dioxide and benzene, while sulfur, sulfoxide, or the sulfone group under same conditions remained stable. The initial degradation temperature was slightly higher than 400 °C, which was in accordance with the literature report of sulfur-containing PIs …”

Section: Resultssupporting

confidence: 92%

“…Therefore, with the combined effort of flexible thio-ether and aliphatic moieties, melt processability was significantly improved, especially when operated at a relatively low processing temperature. The complex viscosity rose smoothly as temperature went down, indicating good melt stability within the test scope . A more rigid structure brought by ketone or a sulfone moiety to the sulfur unit was believed to manifest itself as temperature rose.…”

Section: Resultsmentioning

confidence: 95%

See 1 more Smart Citation

Thermal Plastic and Optical Transparent Polyimide Derived from Isophorone Diamine and Sulfhydryl Compounds

Yan

et al. 2019

Ind. Eng. Chem. Res.

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A series of thermoplastic and optical transparent polyimide-bearing aliphatic rings were manufactured through a two-step approach. The solubility and melt processability were significantly enhanced after embedded with flexible thio-ether moieties. The complex viscosity was within 225.6–3980 Pa·s from 330 to 300 °C. The modified polyimide exhibited moderate mechanical strength to 76 MPa. The 5% thermal weight loss temperature was around 443 °C, with a glass transition temperature of 204.6–234.8 °C. Although the cyclic aliphatic segments endowed the obtained PIs with improved optical performance, the transmittance could be up to 82% at 450 nm, while the transmittance of industrialized thermoplastic polyimide derived from PMDA and ODA was less than 20% under the same condition.

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Section: Resultssupporting

confidence: 92%

Section: Resultsmentioning

confidence: 95%

Thermal Plastic and Optical Transparent Polyimide Derived from Isophorone Diamine and Sulfhydryl Compounds

Yan

et al. 2019

Ind. Eng. Chem. Res.

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“…The PIs reported in this study showed higher refractive indices than previously reported by Guan et al, who worked with PIs having a higher sulfur content than those of the current study. 49 For the linear polyimides, we calculated the theoretical refractive index values (n calcd ) according to the molar refraction formula proposed by Lorentz and Lorenz 23 (R LL ), and they are as reported in Tables 5 and S2.…”

Section: Polymerization and Polymer Film Preparationsmentioning

confidence: 99%

Sulfur-Rich Polyimides Containing Bis(3-(trifluoromethyl)phenyl)thiophene for High-Refractive-Index Applications

et al. 2022

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Three series of sulfur-containing polyimides with the bis(3-(trifluoromethyl)phenyl)thiophene moiety were reported. The synthesis of high-refractive-index polyimides was carried out using a nucleophilic substitution reaction. For that, two new sulfur-containing aromatic amino monomers were developed, one bifunctional and one trifunctional. The monomer and polymer structures were successfully characterized by NMR and Fourier transform infrared (FTIR) spectroscopic methods. Free-standing polyimide films of ∼10 μm were prepared, and they were found to have high thermodynamic stability with T g as high as 257 °C and T d5% above 500 °C. The films were flexible as well as tough with up to 16 ± 7% elongation at break, with a Young’s modulus of 2.6 ± 5 GPa. Indication for melt processability of one of the polyimides was also demonstrated at a temperature of 30 °C above its T g. Thin films with thickness in the nanometer range were coated over modified Si-wafers. Increase in the sulfur and aromatic contents in the polymer backbone resulted in the increase of their refractive index; thus, the polymers synthesized in this work exhibited refractive index as high as 1.76 at 589 nm. The transmittance and birefringence of the polyimides were found to improve by modification in the chemical structure. The tuneable optical properties and good dynamic stability of the polyimides make them potential candidates in optoelectronic applications.

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“…In general, the introduction of rigid heteroaromatic pyridine ring into the polymer chain could endow aromatic polyimides with excellent thermal stability. 35 –37 Guan et al 37 reported a series of polyimides containing pyridine and sulfur units with outstanding thermal stability, excellent mechanical, and good optical properties.…”

Section: Introductionmentioning

confidence: 99%

Design and synthesis of high heat-resistant, soluble, and hydrophobic fluorinated polyimides containing pyridine and trifluoromethylthiophenyl units

Huang

Liu

et al. 2017

High Performance Polymers

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In this study, a novel diamine monomer, 4-(4-trifluoromethylthiophenyl)-2,6-bis(4-aminophenyl)pyridine (FTPAP) was synthesized through two-step reaction from 4-trifluoromethylthiobenzaldehyde and 4-nitroacetophenone as raw materials, and then the structure of FTPAP was characterized by Fourier transform infrared (FTIR) spectroscopy, nuclear magnetic resonance, and mass spectrometry. A series of fluorinated polyimides were prepared from FTPAP with five commercial dianhydrides, namely, pyromellitic dianhydride, biphenyl tetracarboxylic dianhydride, oxydiphtahalic anhydride, benzophenone tetracarboxylic dianhydride, and 4,4′-(hexafluoroisopropylidene) diphthalic anhydride. The structure and performance of the fluorinated polymers were fully characterized by FTIR, differential scanning calorimetry, thermogravimetric analysis, and wide-angle X-ray diffraction (WAXD). The inherent viscosity of polymers ranged from 0.41 to 1.45 dL g−1. These polymers displayed good solubility in polar aprotic solvents, such as N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, and N-methyl-2-pyrrolidone, at room temperature or on heating. Furthermore, they exhibited outstanding thermal stability with glass transition temperatures beyond 305°C, and the temperature of 10% weight loss was in the range of 514–573°C with more than 56% residue at 800°C under nitrogen. Moreover, they showed high optical transparency with the cutoff wavelengths in the range of 385–457 nm and excellent hydrophobic property with contact angle in the range of 82.8–97.6°. In addition, the results of WAXD indicated that all of the polymers presented amorphous structure.

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Highly refractive polyimides containing pyridine and sulfur units: synthesis and thermal, mechanical, solubility and optical properties

Cited by 10 publications

References 31 publications

Thermal Plastic and Optical Transparent Polyimide Derived from Isophorone Diamine and Sulfhydryl Compounds

Thermal Plastic and Optical Transparent Polyimide Derived from Isophorone Diamine and Sulfhydryl Compounds

Sulfur-Rich Polyimides Containing Bis(3-(trifluoromethyl)phenyl)thiophene for High-Refractive-Index Applications

Design and synthesis of high heat-resistant, soluble, and hydrophobic fluorinated polyimides containing pyridine and trifluoromethylthiophenyl units

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