Synthesis and properties of new soluble triphenylamine‐based aromatic poly(amine amide)s derived from <i>N,N</i>′‐bis(4‐carboxyphenyl)‐<i>N,N</i>′‐diphenyl‐1,4‐phenylenediamine

Liou, Guey‐Sheng; Hsiao, Sheng‐Huei

doi:10.1002/pola.10552

Cited by 52 publications

(9 citation statements)

References 25 publications

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“…Because of the incorporation of the bulky, propeller-shaped TPA structure along the polymer backbone, all of the polymers were amorphous with good solubilities, good film-forming capabilities and high thermal stabilities. [23][24][25] Polyimide. Aromatic polyimides can be categorized as an important class of materials because of their many desirable characteristics and often replace glass and metals in industrial applications, especially in the semiconductor and electric packaging industries.…”

Section: Introductionmentioning

confidence: 99%

Solution-processable triarylamine-based high-performance polymers for resistive switching memory devices

Yen

Liou

2015

Polym J

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This review summarizes the most widely used mechanisms in high-performance polymeric resistive memory devices, such as charge transfer, space charge trapping and filament conduction. In addition, recent studies of functional high-performance polymers for memory device applications are reviewed, compared and differentiated based on the mechanisms and structural design methods used. By carefully designing the polymeric structure based on these systematically investigated switching mechanisms, almost all types of current memory characteristics can be reproduced, and these memory properties show extremely high endurance during long-term operation, which makes polyimides very suitable materials for memory applications. INTRODUCTION High-performance polymersToday, life without polymers is unimaginable. Polymers have become the major synthetic materials of the 21st century. High-performance polymers (HPPs) are particularly desirable. The synthesis and development of HPPs over the past 30 years have drawn the attention of many polymer scientists and investigators. These polymers generally possess excellent physical deformation resistance and chemical deterioration resistance at high temperatures over long periods of time. The quest for HPPs began in the late 1950s to meet the demands of the military, aerospace, machine-building and electronics industries, among many other industrial applications.Hill and Walker 1 first noted that the incorporation of aromatic segments into a polymer generally results in a notable increase in its thermal stability. For this reason, much of the research work has been directed toward aromatic compositions. Hence, HPPs usually tend to contain large numbers of aromatic units in their structures. Several of these aromatic HPPs have been used for commercial applications, such as aromatic polyamides, polyimides, polyesters, polysulfones, polytriphenylamine and heterocyclic polymers (Scheme 1). Aromatic polyamides (aramids) and polyimides, such as DuPont's Kevlar fiber and Kapton film, respectively, have been well known for a long time and constantly attract more interest than other HPPs for their useful properties, such as excellent thermal and oxidative stabilities, high mechanical strengths, low flammabilities and good chemical and radiation resistances. [2][3][4][5][6][7][8][9][10][11][12][13] However, the rigidity of the backbone and strong hydrogen bonding of these HPPs result in high melting or glass-transition

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Section: Introductionmentioning

confidence: 99%

Solution-processable triarylamine-based high-performance polymers for resistive switching memory devices

Yen

Liou

2015

Polym J

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“…During the past decade, some aromatic polyamides carrying the redox-active triarylamine units have been prepared and evaluated for electrochromic applications. 20 –22 Additionally, in those triarylamine-containing polyamides, it was generally found that the electron-donating substituents such as dimethylamino, 23 methyl, 12 methoxy, 24,25 and tert -butyl groups 26 on the electrochemically active sites of the triarylamine units tended to stabilize the cation radicals and decreased oxidation potential, leading to a significantly enhanced redox and electrochromic stability of the prepared polyamides. However, to our knowledge, little attention has been paid to aromatic polyamides containing triarylamine groups with electron-withdrawing substituents.…”

Section: Introductionmentioning

confidence: 99%

New fluorinated aromatic polyamides based on N,N-bis(4-carboxyphenyl)-4-trifluoromethylaniline

Zhou

Huang

Cheng

et al. 2018

High Performance Polymers

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A new aromatic diacid monomer, N, N-bis(4-carboxyphenyl)-4-trifluoromethylaniline, was synthesized by the substitution reaction of 4-trifluoromethylaniline with 4-fluorobenzonitrile, followed by alkaline hydrolysis of the dinitrile intermediate. Several polyamides with 4-trifluoromethyltriphenylamine moieties were prepared from the diacid and various aromatic diamines via the direct phosphorylation polycondensation. All the polyamides were amorphous and readily soluble in many polar organic solvents such as N, N-dimethylacetamide and N-methyl-2-pyrrolidone, and could be solution-cast into transparent, tough, and flexible films with good mechanical properties. They exhibited good thermal stability with glass transition temperatures of 260–330°C, 10% weight-loss temperatures above 500°C, and char yields higher than 60% at 800°C in nitrogen. These polymers had low dielectric constants of 3.35–3.72 (100 Hz), low water uptake of 1.80–2.60%, and high transparency with an ultraviolet–visible absorption cutoff wavelength in the range of 378–390 nm. Cyclic voltammograms of the polyamide films cast onto an indium-tin oxide–coated glass substrate exhibited a reversible oxidation redox coupled with oxidation half-wave potentials ( E 1/2) of 0.95–1.04 V versus silver/silver chloride in an acetonitrile solution.

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“…Hole-transporting molecules such as TPA derivatives are reported to act as antioxidants for conjugated materials and to inhibit the oxidation of fluorene derivatives, hence considerably reducing the concentration of keto defects [18,28]. The bulky and propeller-shaped TPA structure incorporated into the polymer backbone tends to be packing-disruptive, most of the TPA substituted materials are amorphous, with high thermal stability, good film-forming ability, and good solubility [29][30][31]. Moreover, the propeller like structure of TPA is responsible for a reduced interchain ET to residual fluorenone defects process normally more efficient than the intrachain one [32].…”

Section: Introductionmentioning

confidence: 99%

Deep Blue Light Amplification from a Novel Triphenylamine Functionalized Fluorene Thin Film

et al. 2019

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The development of high performance optically pumped organic lasers operating in the deep blue still remains a big challenge. In this paper, we have investigated the photophysics and the optical gain characteristics of a novel fluorene oligomer functionalized by four triphenylamine (TPA) groups. By ultrafast spectroscopy we found a large gain spectral region from 420 to 500 nm with a maximum gain cross-section of 1.5 × 10−16 cm2 which makes this molecule a good candidate for photonic applications. Amplified Spontaneous Emission measurements (ASE) under 150 fs and 3 ns pump pulses have revealed a narrow emission at 450 nm with a threshold of 5.5 μJcm−2 and 21 μJcm−2 respectively. Our results evidence that this new fluorene molecule is an interesting material for photonic applications, indeed the inclusion of TPA as a lateral substituent leads to a high gain and consequently to a low threshold blue organic ASE.

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Synthesis and properties of new soluble triphenylamine‐based aromatic poly(amine amide)s derived from N,N′‐bis(4‐carboxyphenyl)‐N,N′‐diphenyl‐1,4‐phenylenediamine

Cited by 52 publications

References 25 publications

Solution-processable triarylamine-based high-performance polymers for resistive switching memory devices

Solution-processable triarylamine-based high-performance polymers for resistive switching memory devices

New fluorinated aromatic polyamides based on N,N-bis(4-carboxyphenyl)-4-trifluoromethylaniline

Deep Blue Light Amplification from a Novel Triphenylamine Functionalized Fluorene Thin Film

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