- Highly stable anodic green electrochromic aromatic polyamides: Synthesis and electrochromic properties
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A 4-methoxy-substituted triphenylamine containing the aromatic diamine, 4,4′-diamino-4″-methoxytriphenylamine (2), was synthesized by the caesium fluoride-mediated condensation of p-anisidine with 4-fluoronitrobenzene, followed by palladium-catalyzed hydr
- Chang, Cha-Wen,Liou, Guey-Sheng,Hsiao, Sheng-Huei
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- Copper(I)–creatine complex on magnetic nanoparticles as a green catalyst for N- and O-arylation in deep eutectic solvent
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Immobilization of copper(I) ions on magnetic nanoparticles was performed using surface modification of Fe3O4 with creatine. Fe3O4?creatine-Cu(I) magnetic catalyst was synthesized and applied in C&bond;X cross-coupling reactions with aryl halides in a deep eutectic as a green solvent. The results indicate the Fe3O4?creatine-Cu(I) magnetic nanoparticles showed excellent activity and high stability. In addition, it was revealed that this catalyst can be recycled five times without significant loss in catalytic activity.
- Bagheri, Sepideh,Heydari, Akbar,Pazoki, Farzane,Radfar, Iman
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- Structural effect on the resistive switching behavior of triphenylamine-based poly(azomethine)s
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Linear and hyperbranched poly(azomethine)s (PAMs)-based on triphenylamine moieties are synthesized and used as the functioning layers in the Ta/PAM/Pt resistive switching memory devices. Comparably, the hyperbranched PAM with isotropic architecture and semi-crystalline nature shows enhanced memory behaviors with more uniform distribution of the HRS and LRS resistances.
- Zhang, Wenbin,Wang, Cheng,Liu, Gang,Wang, Jun,Chen, Yu,Li, Run-Wei
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- Highly selective copper-catalyzed monoarylation of aniline
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A series of mono-, bi- and tridendate ligands was investigated in the copper-catalyzed monoarylation of aniline with p-chloronitrobenzene. Excellent selectivities at high conversions were observed when bridged bisimidazolidenes as well as biphenyl-bisalkylphosphines were employed. The X-ray crystal structure of bis(tert-butyl)biphenylphosphine-copper complex indicates a significant binding of the metal center to the aryl moiety and, thus, an almost bidendate coordination mode. Chelating bisphosphines, glycol, phenanthroline or other monoto tridendate ligands led to less selective or productive catalysts.
- Haider, Joachim,Kunz, Klaus,Scholz, Ulrich
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- Construction of electrocatalytic electrodes bearing the triphenylamine nucleus covalently bound to carbon. A halogen dance in protonated aminotriphenylamines
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The triarylamine nucleus has been attached to a carbon fiber electrode by diazotization of an aminotriphenylamine followed by electrochemical reduction. The resulting electrodes can electrocatalyze the oxidation of organic substrates. In acid, 4-amino-4′,4″-dibromotriphenylamine undergoes dismutation into a mixture of amines containing from 0 to 3 bromine atoms.
- Mayers, Brian T.,Fry, Albert J.
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- Structural characterization of triphenylamine (TPA)-based polymers during the oxidative reaction by two-dimensional (2D) infrared correlation study
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This paper reports the oxidative reaction of triphenylamine (TPA)-based polyamide films. A two-dimensional (2D) gradient mapping method and 2D correlation analysis were applied to the ultraviolet-visible (UV-Vis) and infrared (IR) spectra of TPA-based pol
- Bae, Jun,Chae, Boknam,Seo, Hyemi,Jung, Young Mee,Lee, Seung Woo
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- Synthesis and dynamic random access memory behavior of a functional polyimide
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The device under testing was a plastic dynamic random access memory based on a donor-functionalized polyimide (TP6F-PI), which exhibited the ability to write, read, erase, and refresh the electrical states. The device had an ON/OFF current ratio up to 105, promising minimal misreading error. Both the on and off states were stable under a constant voltage stress of 1 V and survived up to 108 read cycles at 1 V. Copyright
- Ling, Qi-Dan,Chang, Feng-Chyuan,Song, Yan,Zhu, Chun-Xiang,Liaw, Der-Jang,Chan, Daniel Siu-Hhung,Kang, En-Tang,Neoh, Koon-Gee
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- Novel aromatic poly(amine-imide)s bearing a pendent triphenylamine group: Synthesis, thermal, photophysical, electrochemical, and electrochromic characteristics
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A new triphenylamine-containing aromatic diamine, N,N-bis(4-aminophenyl)-N′,N′-diphenyl-1,4-phenylenediamine, was synthesized from the animation reaction between 4-aminotriphenylamine and 4-fluoronitrobenzene and subsequent reduction of the dinitro intermediate. A series of novel aromatic poly(amine-imide)s with pendent triphenylamine units were prepared from the newly synthesized diamine and various tetracarboxylic dianhydrides by either a one-step or a conventional two-step polymerization process. All the poly(amine-imide)s were amorphous and readily soluble in many organic solvents such as N-methyl-2-pyrrolidone (NMP), N,N-dimethylacetamide, and chloroform. These polymers could be solution cast into transparent, tough, and flexible films with good mechanical properties. They had useful levels of thermal stability associated with relatively high glass transition temperatures (264-3520°C), 10% weight-loss temperatures in excess of 568°C, and char yields at 800°C in nitrogen higher than 63%. These polymers exhibited strong UV-vis absorption bands at 311-330 nm in NMP solution. The photoluminescence spectra showed maximum bands around 545-562 nm in the green region. The holetransporting and electrochromic properties are examined by electrochemical and spectroelectrochemical methods. Cyclic voltammograms of the poly(amine-imide) films cast onto an indium-tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 0.78 and 1.14 V versus Ag/ AgCl in acetonitrile solution. The poly(amine-imide) films revealed excellent stability of electrochromic characteristics, with a color change from the pale yellowish neutral form to the green and blue oxidized forms at applied potentials ranging from 0.78 to 1.14 V.
- Cheng, Shu-Hua,Hsiao, Sheng-Huei,Su, Tzy-Hsiang,Liou, Guey-Sheng
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- Electrochromic properties of pyrene conductive polymers modified by chemical polymerization
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Pyrene is composed of four benzene rings and has a unique planar melting ring structure. Pyrene is the smallest condensed polycyclic aromatic hydrocarbon, and its unique structural properties have been extensively studied. Pyrene has excellent properties such as thermal stability, high fluorescence quantum efficiency and high carrier mobility. This paper mainly used thiophene, EDOT and triphenylamine groups to enhance the pyrene based π-conjugated system and control the molecular accumulation of organic semiconductors, and improve their charge transport performances. Five kinds of polymer were synthesized and correspondingly characterized. The five kinds of pyrene conductive polymer had outstanding properties in terms of solubility, fluorescence intensity and thermal stability, good film-forming properties, stable electrochromic properties and high coloring efficiency. The coloration efficiency (CE) of PPYTP was as high as 277 cm2C?1, and the switching response time was short. The coloring time of PPYEDOT was 1.3 s and the bleaching time was 3.2 s. The lower impedance will also provide the possibility of such polymers being incorporated into electrochromic devices in the future. In short, the synthesized new pyrene conductive polymers will have wide application prospects in the field of electrochromic materials.
- Chang, Lijing,Hou, Yanjun,Li, Rui,Ma, Yang,Miao, Shoulei,Wang, Cheng,Xu, Haoran,Zhang, Yuhang
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p. 39291 - 39305
(2021/12/27)
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- Isolable Adducts of Tertiary Amines and Dinitrogen Trioxide
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Anhydrous dinitrogen trioxide, N2O3, dissolved in toluene or dichloromethane rapidly forms stable adducts with tertiary amines such triethyl-, tribenzyl-, or trihexyl-amine. With DABCO, 1,4-diazabicyclo[2.2.2]octane it forms a free flowing orange solid. The analytical and spectroscopic data for the DABCO adduct indicate a formula of DABCO(N2O3)2 which has been characterized by IR, Raman, and UV/Vis spectroscopy. The R3N-N2O3 adducts are hydrolytically sensitive oils or solids which rapidly react quantitatively with thiols to give RSNO. The reactivity of the amine adducts is variable, and the products include amine N-oxides, ammonium nitrites, and ammonium nitrates depending upon the adduct, conditions, and substrate. Density functional theory, B3LYP/aug-cc-pvtz, has been used to compare the predicted structures and spectroscopic data for mono and bis adducts. Geometry optimization of the R3N N2O3 adduct gives a weakly bound Lewis acid/base adduct with the amine nitrogen closest to the nitrosyl N with a strongly tilted planar ONNO2 unit.
- Rosadiuk, Kristopher A.,Scott Bohle
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p. 4543 - 4549
(2018/10/31)
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- New donor-acceptor oligoimides for high-performance nonvolatile memory devices
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We report the synthesis, optoelectronic properties, and electrical switching memory characteristics of three new donor-acceptor oligoimides consisting of the electron-donating moieties (triphenylamine or carbazole) and electron-withdrawing phthalimide moieties. The influence of different donor (D)-acceptor (A) arrangements, including D-A-D and A-D-A structures, on the electrical properties was explored. Devices based on D-A-D oligoimides revealed a reversible nonvolatile negative-differential-resistance (NDR) characteristic and excellent stability during operation. Without applying voltage stress, the on and off states of the devices showed no obvious degradation for an operation time of 10 s and 108 read pulses. However, the devices prepared from the A-D-A oligoimide showed only the insulating properties. The different memory characteristic was probably because the terminal donor moieties in the D-A-D structure might facilitate the injection and transporting of the holes. Besides, the D-A-D oligoimide with triphenylamine groups exhibited an on/off ratio of 104, 2 orders of magnitude higher than that with carbazole groups. The mechanism related to electrical switching properties was elucidated through molecular simulation. Thus the significance of D-A-D structure on tuning memory characteristics for memory device applications was revealed.
- Lee, Wen-Ya,Kurosawa, Tadanori,Lin, Shiang-Tai,Higashihara, Tomoya,Ueda, Mitsuru,Chen, Wen-Chang
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experimental part
p. 4487 - 4497
(2012/05/20)
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- TYRE BELT INCORPORATING AN ANTIOXIDANT AGENT
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Tyre belt comprising a rubber composition based on at least one isoprene elastomer, a reinforcing filler, a crosslinking system and an antioxidant agent, characterized in that said antioxidant agent comprises a 4,4′-bis(alkylamino)triphenylamine correspon
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- Electrophilic nitration of triphenylamines as a route to high oxidation potential electrocatalysts. Polynitration, nitrodebromination, and bromine dance
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The nitration of triphenylamine derivatives is facile, readily leading to an introduction of up to three nitro groups at room temperature. The nitration of 4,4′,4″-tribromotriphenylamine results in nitrodebromination on one or more rings and bromination a
- Wu, Xin,Dube, Mufaro A.,Fry, Albert J.
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p. 7667 - 7669
(2007/10/03)
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- Synthesis, luminescence and electrochromism of aromatic poly(amine-amide)s with pendent triphenylamine moietiest
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A new triphenylamine-containing aromatic dicarboxylic acid monomer, N,N-bis(4-carboxyphenyl)-N′,N′-diphenyl-1,4-phenylenediamine (2), was synthesized from the amination reaction between 4-aminotriphenylamine and 4-fluorobenzonitrile and subsequent alkaline hydrolysis of the dinitrile intermediate. A series of novel aromatic poly(amine-amide)s with triphenylamine units in the main chain and as the pendent group were prepared from the newly synthesized dicarboxylic acid and various aromatic diamines. These poly(amine-amide)s were amorphous and readily soluble in many organic solvents. All the polymers could be solution-cast into flexible films with good mechanical properties. They had excellent levels of thermal stability associated with high glass-transition temperatures (226-261°C). These polymers exhibited strong UV-vis absorption bands at 350-365 nm in NMP solution. Their photoluminescence spectra showed maximum bands around 512-543 nm in the green region. The hole-transporting and electrochromic properties are examined by electrochemical and spectroelectrochemical methods. Cyclic voltammograms of the poly(amine-amide) 5a prepared from the dicarboxylic acid monomer 2 with a structurally similar diamine monomer N,N-bis(4-aminophenyl)-N′,N′- diphenyl-1,4-phenylenediamine (4a) exhibited four reversible oxidation redox couples in acetonitrile solution at E1/2 = 0.60, 0.80, 0.97 and 1.13V, respectively. All the poly(amine-amide)s exhibited excellent reversibility of electrochromic characteristics by continuous five cyclic scans between 0.0 to 1.30 V, with a color change from the original pale yellowish neutral form to the green and then to blue oxidized forms. The Royal Society of Chemistry 2005.
- Liou, Guey-Sheng,Hsiao, Sheng-Huei,Su, Tzy-Hsiang
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p. 1812 - 1820
(2008/09/21)
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- Process for the preparation of aminodiphenylamines
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Die Erfindung betrifft ein Verfahren zur Herstellung von Aminodiphenylaminen, insbesondere von 4-Aminodiphenylamin (4-ADPA), durch Umsetzung von Nitrohalogenbenzolen mit Anilinen in Gegenwart einer Base sowie eines Kupfer-Phosphor-Komplexes und anschlie?ender Hydrierung der intermedi?r gebildeten Nitrodiphenylaminen.
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- Process for the preparation of nitrodiphenylamines
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Die Erfindung betrifft ein Verfahren zur Herstellung von Nitrodiphenylaminen durch Umsetzung von Nitrohalogenen mit Anilinen, einer Base und einem Katalysator sowie ein Verfahren zur Herstellung von Aminodiphenylamin durch Hydrierung des intermedi?r hergestellten Nitrodiphenylamins.
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- Multi-maleimides bearing electron-donating chromophores: Reversible fluorescence and aggregation behavior
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A(=)-D, [A(=)]2-D and [A (=)]3-D multi-maleimides and multi-itaconimides bearing electron-donating chromophores display a strong fluorescence quenching due to an intramolecular charge-transfer interaction. The electron-accepting C=C bond plays a key role in the intramolecular quenching. For the isomerization of these multi-itaconimides and Michael additions of these multi-maleimides, their emission behavior is irreversible. For the Diels-Alder additions of these multi-maleimides, their emission behavior is reversible due to the reversible opening and closing of intramolecular charge-transfer pathway. Tris-maleimide TMPA peripherally modified with furfural alcohol displays not only reversible fluorescence behavior but also reversible aggregation behavior. Copyright
- Zhang, Xin,Li, Zi-Chen,Li, Kai-Bo,Du, Fu-Sheng,Li, Fu-Mian
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p. 12200 - 12201
(2007/10/03)
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- Novel CuI/tributyl phosphine catalyst system for amination of aryl chlorides
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A simple and efficient methodology for the synthesis of triarylamines from aryl chlorides in a single step has been demonstrated using a novel Cul/ tributyl phosphine catalyst system with high activity and selectivity (80-87% yield).
- Patil, Nandkumar M.,Kelkar, Ashutosh A.,Nabi, Zahid,Chaudhari, Raghunath V.
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p. 2460 - 2461
(2007/10/03)
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- Synthesis of bismaleimides bearing electron-donating chromophores and their fluorescence behavior during copolymerization
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Bismaleimides and bisitaconimides bearing diphenylmethylamine, triphenylamine, or 2,5-diphenyl-1,3,4-oxadiazole chromophore (symbolized as A(=)-D(*)-A(=)), as well as their saturated model compounds were synthesized, and their steady
- Zhang, Xin,Jin, Ying-Hua,Diao, Hui-Xiang,Du, Fu-Sheng,Li, Zi-Chen,Li, Fu-Mian
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p. 3115 - 3127
(2007/10/03)
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- Study of ultrasound promoted aromatic nucleophilic substitution of halobenzenes with amines
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The sonochemical nucleophilic aromatic substitution of substituted haloarenes with different amines were studied. The reaction course was found to be strongly depended on basicity, bulkiness, and boiling point of amines as well as on the electron-withdrawing property of the substituents.
- Meciarova, Maria,Toma, Stefan,Podlesna, Jana,Kiripolsky, Michal,Cisarova, Ivana
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- KINETICS OF THE REACTION OF THE N-ANIONS OF ARYL- AND DIARYLAMINES WITH p-NITROFLUOROBENZENE IN DIMETHYL SULFOXIDE
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The rate constants for the reactions of the sodium salts of the N-anions of aryl- and diarylamines of identical basicity with p-nitrofluorobenzene in DMSO at 25 deg C have similar values.The Broensted coefficient βNu for the investigated series
- Vlasov, V. M.,Os'kina, I. A.
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p. 1587 - 1592
(2007/10/03)
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- Process for the preparation of 4-nitrodiphenylamines
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With a far shorter reaction time, azeotropic distillation of the water in the condensation of 4-nitrohalogenobenzenes and primary aromatic amines or formyl derivatives thereof in the presence of potassium carbonate and, if appropriate, copper compounds can be dispensed with if the reaction is carried out in the presence of Al metal, Mg metal or Zn metal or mixtures or alloys of these metals.
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- Condensations of 1,4-Cyclohexanediones and Secondary Aromatic Amines. II. N-Phenylation of Diarylamines
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The condensations of 1,4-cyclohexanedione with several diphenylamines were investigated in order to determine the limit of the utility of this reaction for the N-phenylation of aromatic secondary amines. 4-Methoxy-, 4,4'-dimethyl-, and 4,4'-dibromodiphenylamines produced their N-phenylated compounds in fairly good yields, but 4-hydroxy-, 3-methoxy-, and 4,4'-bis(dimethylamino)diphenylamines produced poor yields.Nitro-substituted diphenylamines gave N-phenyl derivatives in low yields along with N-4-hydroxyphenyl derivatives.N,N'-Diphenyl-p-phenylenediamine and N,N'-diphenylbenzidine gave correspondig tetra-N-phenyl diamines in good yields.The condensation of N-phenyl-1-naphthylamine, N-phenyl-2-naphthylamine, di-2-pyridylamine, phenothiazine, and carbazole with 1,4-cyclohexanedione were also examined.
- Haga, Kazuo,Iwaya, Katsumasa,Kaneko, Ryohei
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p. 803 - 808
(2007/10/02)
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