Heat-resistant and photoluminescent indole-based poly(ether sulfone)s

Wei, Wenxuan; Yang, Li; Chang, Guanjun

doi:10.1177/0954008317701823

Cited by 10 publications

(8 citation statements)

References 19 publications

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“…The purity of the intermediate compounds 3, 4, and 6 and the diamine monomer 7 was checked by TLC, which showed one spot in an ethylacetate/cyclohexane mixture (50:50). The chemical structures of the intermediate compounds 3, 4, and 6 and the diamine monomer 7 were proven by FTIR, 1 H NMR and 13 C NMR spectroscopic techniques. The transformation of nitro to amino functionality could be monitored by the change of FTIR spectra.…”

Section: Monomer Synthesismentioning

confidence: 99%

“…9 The polymers based on indole have been used for the applications in electronics, electrocatalysis, anode materials, anticorrosion coatings, and biological areas. [10][11][12][13] Additionally, the indole group was considered as a valid substitute of the carbazole moiety. Polymers containing carbazole groups have been extensively studied and employed in photoconductivity and photorefractive materials owing to its excellent photoconductivity properties.…”

Section: Introductionmentioning

confidence: 99%

“…13 C NMR spectrum of diamine 7 in DMSO-d 6 solution 13. C NMR: Carbon-13 nuclear magnetic resonance; DMSO-d6: dimethyl sulfoxide-d 6 .…”

mentioning

confidence: 99%

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Synthesis and properties of highly organosoluble aromatic polyimides containing N-(4-(di(1H-indole-3-yl)methyl)phenyl) moieties

Khalili

Rafiee

2019

High Performance Polymers

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A new diamine monomer containing indole unit, 3,5-diamino- N-(4-(di(1H-indol-3-yl)methyl)phenyl)benzamide, was successfully synthesized and applied in the preparation of a series of polyimides (PIs) via a conventional two-step polymerization procedure with three aromatic tetracarboxylic dianhydrides. The prepared polymers showed excellent solubility in organic solvents such as N-methyl-2-pyrrolidinone (NMP), N, N-dimethylacetamide, and N, N-dimethylformamide. Flexible and strong films of PIs were obtained via casting from their solutions. The glass transition temperature of these polymers was in the range of 223–264°C. They were fairly stable up to a temperature around 300°C and lost 10% weight at 372°C in nitrogen atmosphere. All of the polymers revealed absorption maxima around 323 nm with a fluorescence emission maxima around 378–406 nm in NMP. The cyclic voltammetry of the PIs exhibited an oxidation wave with a peak at 1.07 V. The resulting polymer films had tensile strengths from 83 MPa to 107 MPa, elongates at break of 7–10%, and tensile moduli of 2.2–2.3 GPa.

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Section: Monomer Synthesismentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis and properties of highly organosoluble aromatic polyimides containing N-(4-(di(1H-indole-3-yl)methyl)phenyl) moieties

Khalili

Rafiee

2019

High Performance Polymers

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“…into the molecular chain of poly (ether nitrile) (PEN) can improve the solubility, and at the same time can endow it new properties, such as fluorescence properties, 22 antifouling property, 21 and so forth. By introducing hydroquinone, 23 bisphenol A, 24 phenolphthalin, 25 and so forth. into the chain of poly (ether sulfone), the obtained polymer not only has good solubility but also reduces the cost.…”

Section: Introductionmentioning

confidence: 99%

Copolymers of poly(aryl ether ketone)/poly(ether ether amide) containing different numbers of methylene in the main chain: Synthesis and properties

Jiang,

Li,

Dai

et al. 2023

J of Applied Polymer Sci

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Abstract“One‐step polymerization method” was used to improve the thermal property of semi‐aromatic poly(ether ether amide) (PEEA). Firstly, a series of difluorobenzamide monomers containing different numbers of methylene were synthesized by the reaction of diamine and 4‐fluorobenzoic chloride using a facile interfacial reaction method. Then, these syntheses were conducted to react with bisphenol AP and 4,4′‐difluorobenzophenon to synthesize the novel poly(aryl ether ketone)/semi‐aromatic poly(ether ether amide) copolymers (PAEK/PEEA) with different chain lengths in the chain through nucleophilic substitution by a one‐step method. The obtained copolymers were amorphous with inherent viscosities of 0.373–0.433 dLg−1. They were found to have high glass transition temperatures (Tg) of 160–191°C, good thermal stability with 5% weight‐loss temperature (T5%) of 409–437°C. The tensile strengths of the copolymers were 65.0–75.8 MPa. The storage modulus were over 0.9 GPa at 120°C. At room temperature, the copolymers were soluble in NMP, slightly soluble in DMF, CH2Cl2, CH3Cl, indicating that the synthesized copolymers could be processed by solution method. The results of optical performance showed that the copolymers had good optical transmittance with the optical transmittance of 75.7%–86.1% at 450 nm. They have the potential to be applied as the novel heat‐resistance optical films as the novel copolymers.

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“…Surprisingly, little attention has been paid to the development of indole-based polyesters. In the literature, the use of indole structures has been limited to conducting polymers and microporous materials, − polymers with indole pendant groups, polyethersulfones, and poly( N -arylene diindolylmethane)s. − There was only one report in the 1980s describing bis-indole-containing polyesters without the characterization of properties . Recently, a new series of fully bio-based polyesters were synthesized and reported by our group using a new indole-based dicarboxylate monomer and five different aliphatic diols .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Thermal Properties, and Rheological Characteristics of Indole-Based Aromatic Polyesters

Arza

Zhang

2019

ACS Omega

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Currently, there is an intensive development of bio-based aromatic building blocks to replace fossil-based terephthalates used for poly(ethylene terephthalate) production. Indole is a ubiquitous aromatic unit in nature, which has great potential as a bio-based feedstock for polymers or plastics. In this study, we describe the synthesis and characterization of new indole-based dicarboxylate monomers with only aromatic ester bonds, which can improve the thermal stability and glass-transition temperature (Tg) of the resulting polyesters. The new dicarboxylate monomers were polymerized with five aliphatic diols to yield 10 new polyesters with tunable chemical structures and physical properties. Particularly, the Tg values of the obtained polyesters can be as high as 113 °C, as indicated by differential scanning calorimetry and dynamic mechanical analysis. The polyesters showed decent thermal stability and distinct flow transitions as revealed by thermogravimetric analysis and rheology measurements.

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Heat-resistant and photoluminescent indole-based poly(ether sulfone)s

Cited by 10 publications

References 19 publications

Synthesis and properties of highly organosoluble aromatic polyimides containing N-(4-(di(1H-indole-3-yl)methyl)phenyl) moieties

Synthesis and properties of highly organosoluble aromatic polyimides containing N-(4-(di(1H-indole-3-yl)methyl)phenyl) moieties

Copolymers of poly(aryl ether ketone)/poly(ether ether amide) containing different numbers of methylene in the main chain: Synthesis and properties

Synthesis, Thermal Properties, and Rheological Characteristics of Indole-Based Aromatic Polyesters

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