Synthesis, optical and electrochemical properties of new hyperbranched poly(triphenylamine amide)s

Wang, Kun‐Li; Huang, Sheng‐Tung; Hsieh, Li-Ga; Huang, Guo-Syun

doi:10.1016/j.polymer.2008.07.053

Cited by 26 publications

(14 citation statements)

References 26 publications

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“…The precipitated orange solid was collected by filtration and washed with methanol. The product yield was 5.71 g (70%); 1 …”

Section: Synthesis Of 44 -Dinitro-methoxytriphenylamine 32mentioning

confidence: 99%

“…Organic charge transporting materials play import roles in many electrical and optical applications, such as organic photoconductors, electroluminescence (EL) and electrochromic devices [1][2][3][4][5]. In particular, electrochromic devices exhibit a reversible optical change in absorption or transmittance after being oxidized or reduced electrochemically by applying an external voltage using electrochromic materials, such as transition-metal oxides, inorganic coordination complexes, organic molecules, and conjugated polymers [6][7][8][9][10][11].…”

Section: Introductionmentioning

confidence: 99%

“…Triphenylamine (TPA) derivatives have attracted considerable interest over the past few decades owing to their excellent charge transporting properties as hole transporting materials in thin layer electro-optical devices, such as organic light-emitting diodes, solar cells, organic field effect transistors and photorefractive holography [1][2][3][4][12][13][14][15][16]. The basic electrical properties of the TPA derivatives are the easy oxidizability of the amino center and its ability to transport the positive charge centers via cationic radical species [17].…”

Section: Introductionmentioning

confidence: 99%

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Electrochromism Properties of Polyimides Possessing Triphenylamine Moieties with Different Substituents

Lee

Bae

Seo

et al. 2014

Molecular Crystals and Liquid Crystals

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Two diamine monomers with methyl (CH3TPA) and methoxy (OCH3TPA) group substituents in the para position of the triphenylamine (TPA) moiety were synthesized by nucleophilic aromatic substitution using 4-fluoronitrobenzene with p-toluidine and p-anisidine, respectively. From these diamine monomers, electroactive polyimides (PI)s were prepared by the chemical imidization of poly(amic acid) solutions, which were prepared with 4,4 -oxydiphthalic anhydride (ODPA). 1 H nuclear magnetic resonance and Fourier transform infrared spectroscopy confirmed that both PIs had been synthesized successfully. The measured inherent viscosity for ODPA-CH3TPA PI and ODPA-OCH3TPA PI was 0.42 and 0.49 dL/g, respectively. The glass transition temperatures for ODPA-CH3TPA PI and ODPA-OCH3PDA PI were 236 • C and 238 • C, respectively, and the thermal degradation temperature of both PIs was above 390 • C. The band gaps of ODPA-CH3PDA and ODPA-OCH3PDA were 3.00 and 2.72 eV, respectively. The oxidation onset potential E ox of ODPA-CH3PDA PI and ODPA-OCH3PDA PI from cyclic voltammetry was 0.73 V and 0.65 V, respectively. The highest occupied molecular orbital and lowest unoccupied molecular orbital values differed according to the groups substituted into the triphenylamine moiety. After applying a voltage, the absorption peak intensity at 723 nm and 752 nm for ODPA-CH3TPA and ODPA-OCH3TPA, respectively, increased. The electrical properties varied according to the chemical structure of synthesized diamines.

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“…The precipitated orange solid was collected by filtration and washed with methanol. The product yield was 5.71 g (70%); 1 …”

Section: Synthesis Of 44 -Dinitro-methoxytriphenylamine 32mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Electrochromism Properties of Polyimides Possessing Triphenylamine Moieties with Different Substituents

Lee

Bae

Seo

et al. 2014

Molecular Crystals and Liquid Crystals

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“…[1][2][3][4][5][6][7][8][9][10][11][12] Combining of chemically stable amide bonds with hyperbranched structures not only retained excellent thermal and flame-resistant properties of aromatic polyamides, but also decreased melt viscosity and excellent solubility which improved the processability. [13][14][15][16][17][18][19][20] Moreover, introduction of flexible aliphatic units into the main chain is another method to improve the processability of aromatic polyamides. This type of aromaticaliphatic polyamides was known as glass-clear nylons with exceptional properties.…”

Section: Introductionmentioning

confidence: 99%

Phosphorus-containing polymers from THPS. II: synthesis and property of phosphorus-containing hyperbranched aromatic-aliphatic polyamides

Tan

Sun

Zhang

et al. 2015

Designed Monomers and Polymers

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Phosphorus-containing hyperbranched aromatic-aliphatic polyamides are prepared via direct polymerization of triacid (B 3 ) with different diamines (A 2 ), which for improving the processability of aromatic polyamides while keeping exellent thermal and mechanical property. The triacid (B 3 ), tris(2-carboxyethyl)phosphine oxide (TCEPO), is synthesized from tetrakis(hydroxymethyl)phosphonium sulfate and its structure is verified by Fourier transform infrared, 1 H, 13 C and 31 P NMR spectroscopy. Then, the polycondensation reaction of TCEPO with p-phenylene diamine, 4,4′-oxyphenylene diamine and 4,4′-methylenedianiline result in three phosphorus-containing hyperbranched aromatic-aliphatic polyamides, and the degree of branching is found between 0.66 and 0.71. Gel permeation chromatography measurement reveal that all hyperbranched aromatic-aliphatic polyamides have moderate number-averaged molecular weights and narrow molecular weight distribution. The Dynamic mechanical thermal analysis results show all polymers have two glass transition temperatures (T g ) in the temperature range 85.3-128.0°C and have high storage modulus about 1.52-3.19 GPa at 50°C. The TGA results reveal the initial degradation temperatures (T 5 ) and the temperatures for 10% gravimetric loss (T 10 ) for the hyperbranched aromatic-aliphatic polyamides are in the range of 214-250 and 256-333°C, and the maximum decomposition temperatures (T m ) are about 500°C, and also the char yields of polymers at 850°C are about 39.4-48.4%, which indicate good thermal stability.

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“…Triphenylamine (TPA) derivatives have showed excellent thermal, electrochemical stability, electron‐donating ability, and optoelectronic properties 7. They have been used as advanced materials for polymer memories,8–14 electroluminescence,15 chemosensor application,16, 17 and electro‐optical devices 18. Because of a noticeable change of coloration, TPA derivatives are regarded as good EC materials 19–22.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and optoelectronic properties of novel organosoluble polynorbornenes containing asymmetric pyrenyl and electroactive substituents via ring‐opening metathesis polymerization

Lian

Huang

et al. 2011

J. Polym. Sci. A Polym. Chem.

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Novel polynorbornenes, poly(NBPYTPA), and poly (HNBPYTPA), containing chromophoric and electroactive groups were synthesized by ring-opening metathesis polymerization using Grubbs' catalysts and followed hydrogenation, respectively. The glass transition temperatures (T g ) of poly(NBPYTPA) and hydrogenated poly(HNBPYTPA) were 195 and 165 C, respectively. The 10% weight-loss temperatures of hydrogenated poly (HNBPYTPA) and poly(NBPYTPA) were up to 465 and 420 C, respectively. The photoluminescence emission spectra of poly (HNBPYTPA) showed strong solvatochromic property, revealing that poly(HNBPYTPA) underwent remarkable bathochromic shifts with an increase in solvent polarity. The cyclic voltammogram of poly(HNBPYTPA) film cast onto an indium tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 0.8 and 1.2 V versus Ag/Ag þ in acetonitrile solution. The electrochromic characteristics of poly(HNBPYTPA) showed reversibility, with color changes from yellow to blue and then to red upon the application of potentials from 0 to 1.3 V. V C 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 49: 5350-5357, 2011

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Synthesis, optical and electrochemical properties of new hyperbranched poly(triphenylamine amide)s

Cited by 26 publications

References 26 publications

Electrochromism Properties of Polyimides Possessing Triphenylamine Moieties with Different Substituents

Electrochromism Properties of Polyimides Possessing Triphenylamine Moieties with Different Substituents

Phosphorus-containing polymers from THPS. II: synthesis and property of phosphorus-containing hyperbranched aromatic-aliphatic polyamides

Synthesis and optoelectronic properties of novel organosoluble polynorbornenes containing asymmetric pyrenyl and electroactive substituents via ring‐opening metathesis polymerization

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