- A Pd/Cu-Free magnetic cobalt catalyst for C-N cross coupling reactions: synthesis of abemaciclib and fedratinib
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Herein, the synthesis of a nano-catalytic system comprising magnetic nanoparticles as the core and edible natural ligands bearing functional groups as supports for cobalt species is described. Subsequent to its characterization, the efficiency of the catalyst was investigated for C-N cross-coupling reactions using assorted derivatives of amines and aryl halides. This novel and easily accessible Pd- and Cu-free catalyst exhibited good catalytic activity in these reactions using γ-valerolactone (GVL) at room temperature; good recyclability bodes well for the future application of this strategy. The introduced catalytic system is attractive in view of the excellent efficiency in an array of coupling reactions and its versatility is illustrated in the synthesis of abemaciclib and fedratinib, which are FDA-approved new and significant anti-cancer medicinal compounds that are prepared under green reaction conditions.
- Hajipour, Abdol R.,Khorsandi, Zahra,Sarfjoo, Mohamad Reza,Varma, Rajender S.
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supporting information
p. 5222 - 5229
(2021/07/29)
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- Near-Infrared Boron Difluoride Formazanate Dyes
-
Near-infrared (NIR) dyes are sought after for their utility in light harvesting, bioimaging, and light-mediated therapies. Since long-wavelength photoluminescence typically involves extensive π-conjugated systems of double bonds and aromatic rings, it is often assumed that NIR dyes have to be large molecules that require complex syntheses. We challenge this assumption by demonstrating that facile incorporation of tertiary amine groups into readily available 3-cyanoformazans affords efficient production of relatively simple NIR-active BF2 formazanate dyes (λabs=691–760 nm, λPL=834–904 nm in toluene). Cyclic voltammetry experiments on these compounds reveal multiple reversible redox waves linked to the interplay between the tertiary amine and BF2 formazanate moieties. Density-functional calculations indicate that the NIR electronic transitions in BF2 formazanates are of π→π*-type, but do not always involve strong charge transfer.
- Buguis, Francis L.,Maar, Ryan R.,Staroverov, Viktor N.,Gilroy, Joe B.
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supporting information
p. 2854 - 2860
(2021/01/20)
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- Metal-organic frameworks derived CuONPs@C nanocatalysts for synthesizing optoelectronic triarylamine molecules
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Carbon encapsulated copper oxide nanoparticles (CuONPs@C) fabricated using copper metal organic frameworks (Cu-MOFs) used as reusable nanocatalysts in Ullmann C[sbnd]N coupling reactions for synthesizing optoelectronic triphenylamine (TPA) and carbazole (CBZ) derivatives. The formation of CuONPs in carbon matrix was confirmed by powder X-ray diffraction (PXRD), X-ray photoelectron spectroscopy (XPS) and high-resolution transmission electron microscopy (HR-TEM). The catalytic activity of CuONPs@C was performed with diphenylamine/carbazole with substituted aryl halides in presence of mild K2CO3 base that produced triarylamines with 63–83% yields. Carbazole triarylamines exhibited strong solid state fluorescence (Φf = 14.54–36.32%) with λmax between 370 and 420 nm.
- Kundu, Anu,Kumar, Vadivel Vinod,Anthony, Savarimuthu Philip
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- Emergence of Aggregation Induced Emission (AIE), Room-Temperature Phosphorescence (RTP), and Multistimuli Response from a Single Organic Luminogen by Directed Structural Modification
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Multifunctional organic luminogens exhibiting simultaneous aggregation induced emission (AIE), room-temperature phosphorescence (RTP), and mechanochromism have recently attracted considerable attention owing to their potential applications in optoelectronics and bioimaging. However, a comprehensive correlation among these three distinguished properties is yet to be unveiled, which will help to decipher defined methodologies to design future generation multifunctional organic materials. Herein, we have demonstrated a route to obtain a multifunctional organic luminogen, starting from an ACQphore (TPANDI) by simple structural engineering. We have shown that a slight reduction in length of the planar acceptor moieties can effectively inhibit the undesirable π-πstacking interaction between molecules in the condensed state and thereby cause an ACQ to AIE type transformation from TPANDI to TPANMI and TPAPMI. Both TPANMI and TPAPMI exhibit RTP properties (even in ambient condition) because of the presence of a reasonably low singlet-triplet energy gap (δEST). In our study, these two luminogens were found to be mechano-inactive. Interestingly, an insertion of cyano-ethylene group and benzene linker in between the triphenylamine and phthalimide moieties introduced another luminogen TPACNPMI, which can simultaneously exhibit AIE, RTP, and mechanochromic properties.
- Chatterjee, Abhijit,Chatterjee, Joy,Sappati, Subrahmanyam,Sheikh, Tariq,Umesh, Rintu M.,Ambhore, Madan D.,Lahiri, Mayurika,Hazra, Partha
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p. 12832 - 12846
(2021/11/24)
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- Ferrocene modified triphenylamine derivative electrochromic composite material and preparation method thereof (by machine translation)
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The invention discloses a ferrocene modified triphenylamine derivative compound electrochromism material and a preparation method thereof,and the preparation method 4 - comprises the following steps: firstly, the preparation method of the ferrocene-containing diphenylamine dimer comprises the, following steps: firstly, carrying out an oxidation-reduction 4,4' - reaction with perchloric acid; copper 4,4' - 4,4' - Vilsmerier . (by machine translation)
- -
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Page/Page column 6; 10; 12; 14
(2020/02/17)
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- Triphenylamine derivative electrochromic composite material and preparation method thereof
-
The invention discloses a triphenylamine derivative electrochromic composite material and a preparation method thereof. The preparation method comprises the following steps: preparing 4-nitrotrianiline from diphenylamine, K2CO3 and fluoronitrobenzene, pro
- -
-
Paragraph 0044-0048; 0069-0073; 0094-0098
(2020/02/14)
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- A Schiff base based on triphenylamine and thiophene moieties as a fluorescent sensor for Cr (III) ions: Synthesis, characterization and fluorescent applications
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A Schiff base fluorescent sensor was designed for selective detection of Cr3+ ions in aqueous solution. The procedure for the study was fulfilled in three steps which comprised the synthesis of 4-nitro-triphenylamine (TPA-NO2), 4-amino-triphenylamine (TPA-NH2) and Schiff base (TPA-Th) using 2,2′-bithiophene-5-carboxaldehyde, respectively. Structural characterization of the purely synthesized compounds was acquired by using UV–Vis, FT-IR, 1H NMR and 13C NMR analyses. Their electrochemical, thermal, and the optical sensor properties for metal ions were enlightened by cyclic voltammetry (CV), thermal-TG-DTA and photoluminescence (PL) techniques, respectively. Non-fluorescent TPA-Th displayed a fluorescence enhancement after chelation with Cr3+ ions with high selectivity and overall emission change of 59-fold at an excitation wavelength of 320 nm. The limit of detection (LOD) value was as low as 1.5 × 10?6 M for Cr3+ ions, accompanied by an association constant (Ka) of 2.8 × 104 M?1. TPA-Th was beneficial for the design and development of metal-complexed fluorescent sensor and light emitting devices.
- Erdener, Di?dem,Kaya, ?smet,Kolcu, Feyza
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- Non-doped organic light-emitting diodes based on phenanthroimidazole-triphenylamine derivatives with a low efficiency roll-off of 9% at a high luminance of 10?000 cd m-2
-
Simultaneously achieving high exciton utilization efficiency (ηS) and a low efficiency roll-off at high brightness is challenging for fluorescent organic light-emitting diodes (OLEDs). In this work, we tried to realize this goal by constructing "hot exciton"materials by fine-tuning the lowest triplet excited state (T1) features. Two phenanthroimidazole-triphenylamine based donor-acceptor (D-A) derivatives TPPI-AQ and TPPI-BZPCN have been designed and synthesized. The photophysical studies and theoretical calculations reveal that TPPI-BZPCN has an obvious "hot exciton"feature and an aggregation-induced emission (AIE) characteristic. A big gap between T1 and T2 exists in TPPI-BZPCN which provides the possibility for a reverse intersystem system crossing (RISC) process from the upper energy level of T2 to S1. As a result, the non-doped electroluminescent device based on TPPI-BZPCN achieves a maximum external quantum efficiency (EQE) of 3.33%. The electroluminescence (EL) spectrum exhibits an emission peak at 592 nm, and the brightness can be up to 55?657 cd m-2. Also, the device is able to retain an EQE of 3.03% at the high luminance of 10?000 cd m-2, with a very low efficiency roll-off of 9%, which is the lowest efficiency roll-off currently reported in the orange-red emitters based on the "hot exciton"mechanism. Moreover, the ηS of the non-doped device reaches 48%, which exceeds the limitation of 25% in conventional fluorescence OLEDs.
- Du, Chunya,Feng, Zijun,Gao, Lei,He, Xin,Jiang, Dongyan,Liu, Futong,Liu, Hui,Lu, Ping
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supporting information
p. 14446 - 14452
(2020/11/09)
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- One-way valveN-Preparation method of aryl substituted heterocyclic compound (by machine translation)
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The invention relates to the technical field of organic chemical synthesis, in particular to an organic chemical synthesis technology. NThe preparation method comprises ?timetime?: 3 molar ratio, reaction 30 - 60 minutes at normal temperature and normal pressure, water adding quenching after reaction, organic solvent extraction 1:1-1 and column chromatography separation (V). Petroleum ether : VEthyl acetate =40:1 - 20:1). NAryl substituted heterocyclic derivatives. Nitrobenzene is used as Ar-H source. N-methylaniline. N-ethylaniline. N-methyl-heterocycles, tetrahydroquinoline, and the like can be used as the amine source. t- BuBuBuBuBuBuBuONa/DMSO/O2 In the system, a direct arylamine reaction of the aromatic ring is achieved. This process has the advantage that the process is simple and high in atomic economy, avoiding the use of expensive transition metals, mild reaction conditions, and environmental-friendly by-products. (by machine translation)
- -
-
Paragraph 0019
(2020/11/01)
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- 3-(Ethoxycarbonyl)-1-(5-methyl-5-(nitrosooxy)hexyl)pyridin-1-ium cation: A green alternative to tert-butyl nitrite for synthesis of nitro-group-containing arenes and drugs at room temperature
-
Due to their remarkable properties, task-specific ionic liquids have turned out to be progressively popular over the last few years in the field of green organic synthesis. Herein, for the first time, we report that a new task-specific nitrite-based ionic liquid such as 3-(ethoxycarbonyl)-1-(5-methyl-5-(nitrosooxy)hexyl)pyridin-1-ium bis(trifluoromethanesulfonyl)imides (TS-N-IL) derived from biodegradable ethyl nicotinate indeed acted as an efficient and eco-friendly reagent for the synthesis of highly valuable nitroaromatic compounds and drugs including nitroxynil, tolcapone, niclofolan, flutamide, niclosamide and nitrazepam. The bridging of an ionic liquid with nitrite group not only increases the yield and rate of direct C[sbnd]N bond formation reaction but also allows easy product separation and recyclability of a byproduct. Nonvolatile nature, easy synthesis, merely stoichiometric need and mildness are a portion of the extra focal points of TS-N-IL while contrasted with tert-butyl nitrite an outstanding and highly-flammable reagent utilized largely in organic synthesis.
- Chaudhary, Renu,Natarajan, Palani,Rani, Neetu,Sakshi,Venugopalan, Paloth
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supporting information
(2019/12/30)
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- Acid pH probe compound and production method thereof
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The invention relates to the technical field of fluorescence probes, in particular to an acid pH probe compound and a production method thereof. Triphenylamine compounds can be used as induced luminescence materials due to good fluorescence performance, and a schiff base structure has good coordination capability and protonation capability so that triphenylamine schiff base fluorescence compoundscan be used as pH sensing materials excellent in performance. However, the stability, especially in an acid water environment, of the schiff base structure under an acid condition is not ideal, and hydrolysis is prone to happen so that most of the schiff base structure pH probe compounds can hardly adapt to detection under strong acid water body conditions. The invention provides the acid pH fluorescence probe compound novel in structure; and the acid pH probe compound novel in structure has a good response effect in a pH range of 2-7, can adapt to strong acid water body environments, and hasimportant significance when applied for water body detection.
- -
-
Paragraph 0048-0050; 0057-0059
(2019/07/04)
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- Ultrafine hybrid Cu2O-Fe2O3 nanoparticles stabilized by hexaphenylbenzene-based supramolecular assemblies: A photocatalytic system for the Ullmann-Goldberg coupling reaction
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Ultrafine hybrid Cu2O-Fe2O3 NPs have been prepared using the supramolecular assemblies of hexaphenylbenzene (HPB) derivative 3 as nanoreactors and stabilizers. The as-prepared hybrid Cu2O-Fe2O3 NPs serve as an efficient and recyclable photocatalytic system for carrying out C-N coupling between aryl halides and various amines (aliphatic, aromatic and N-heterocyclic) at room temperature in mixed aqueous media under visible light irradiation. Amazingly, Cu2O-Fe2O3 NPs also exhibited high efficiency in the reactions involving the synthesis of biologically important N-substituted carbazole derivatives. The work being presented in this article demonstrates the preparation of a 'dip strip' coated with the as-prepared catalytic system and utilization of this paper strip as a recyclable and portable heterocatalytic system for carrying out the Ullmann-Goldberg coupling.
- Singh, Gurpreet,Kumar, Manoj,Bhalla, Vandana
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p. 5346 - 5357
(2018/12/05)
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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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- Copper(I)-USY as a Ligand-Free and Recyclable Catalyst for Ullmann-Type O-, N-, S-, and C-Arylation Reactions: Scope and Application to Total Synthesis
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The copper(I)-doped zeolite CuI-USY proved to be a versatile, efficient, and recyclable catalyst for various Ullmann-type coupling reactions. Easy to prepare and cheap, this catalytic material enables the arylation and heteroarylation of diverse O-, N-, S-, and C-nucleophiles under ligand-free conditions while exhibiting large functional group compatibility. The facility of this catalyst to promote C-O bond formation was further demonstrated with the total synthesis of 3-methylobovatol, a naturally occurring diaryl ether of biological relevance. From a mechanistic viewpoint, two competitive pathways depending on the nature of the nucleophile and consistent with the obtained results have been proposed.
- Garnier, Tony,Danel, Mathieu,Magné, Valentin,Pujol, Anthony,Bénéteau, Valérie,Pale, Patrick,Chassaing, Stefan
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p. 6408 - 6422
(2018/05/31)
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- Chitosan-Supported Ni particles: An Efficient Nanocatalyst for Direct Amination of Phenols
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A practical method for the direct amination of phenols using 2,4,6-trichloro-1,3,5-triazine (TCT) as an efficient promotor for the activation of phenols in the presence of an efficient and recyclable heterogeneous catalyst prepared by immobilization of nickel particles on triazole modified chitosan is described. This heterogeneous catalyst has demonstrated a promising activity for the conversion of phenolic compounds to their corresponding amine under mild conditions. Moreover, the obtained catalyst can be reused in five consecutive runs with consistent catalytic activity.
- Hajipour, Abdol R.,Abolfathi, Parisa
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- Solvent-free mechanochemical Buchwald-Hartwig amination of aryl chlorides without inert gas protection
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A solvent-free Buchwald-Hartwig amination had been developed under high-speed ball-milling conditions, which afforded the desired products with moderate to high yields. The addition of sodium sulfate was found to be crucial for improving both the performance and the reproducibility. Comparative solvent-free stirring experiments implicated the importance of mechanical interaction for the transformation, and the inert gas was proved to be unnecessary for this amination.
- Shao, Qiao-Ling,Jiang, Zhi-Jiang,Su, Wei-Ke
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supporting information
p. 2277 - 2280
(2018/05/16)
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- Efficient and straightforward click synthesis of structurally related dendritic triazoles
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A simple, rapid and efficient copper-catalyzed 1,3-dipolar cycloaddition reaction is described for the synthesis of a novel family of twelve triazolic dendrimers structurally related. The products were the result of the click reaction of three cores and four different azides in tetrahydrofuran applying a homogeneous copper catalysis. The reaction intermediates and products were obtained in very good to excellent yields using straightforward and simple work-up procedures. This new family of compounds contain electroactive moieties such as carbazole and triphenylamine which may turn them into excellent candidates for the development of optoelectronic organic materials.
- Mangione,Spanevello,Anzardi
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p. 47681 - 47688
(2017/10/23)
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- Solvent-Free Buchwald-Hartwig (Hetero)arylation of Anilines, Diarylamines, and Dialkylamines Mediated by Expanded-Ring N-Heterocyclic Carbene Palladium Complexes
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A highly efficient solvent-free protocol for the Buchwald-Hartwig (hetero)arylation of anilines, diarylamines, and dialkylamines mediated by the expanded-ring N-heterocyclic carbene palladium complex (THP-Dipp)Pd(cinn)Cl [THP-Dipp = 1,3-bis(2,6-diisopropylphenyl)-3,4,5,6-tetrahydropyrimidin-2-ylidene; cinn = cinnamyl, 3-phenylallyl] was developed. The catalytic protocol was efficient for the coupling of amines and (hetero)aryl chlorides and bromides bearing donor, acceptor, and bulky substituents.
- Topchiy, Maxim A.,Dzhevakov, Pavel B.,Rubina, Margarita S.,Morozov, Oleg S.,Asachenko, Andrey F.,Nechaev, Mikhail S.
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supporting information
p. 1908 - 1914
(2016/04/20)
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- An efficient heterogeneous ligand free C-N coupling reaction catalyzed by palladium supported on magnetic nanoparticles
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The catalytic activity of palladium supported on magnetic nanoparticles in the amination coupling reaction of different nitrogen containing substrates with aryl halides was investigated. C-N bond formation was achieved in moderate to excellent yields and the catalyst could be separated by magnetic decantation.
- Rafiee, Ezzat,Ataei, Ali,Joshaghani, Mohammad
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p. 219 - 222
(2015/12/31)
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- Preparation and electrochromic properties of two series of polyurethanes containing separated triphenylamine moiety with different blocks
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Two series of novel aromatic polyurethanes containing triphenylamine derivatives were synthesized via polycondensation of 4-(3,6-diisocyanato-9H-carbazol-9-yl) aniline, N,N-bis(4-isocyanatophenyl) benzene-1,4-diamine with various dihydroxy monomers such as phenolphthalein, 2,2-bis (4-hydroxyphenyl) -propane, 4,4'-dihydroxybiphenyl, 4, 4'-bishydroxy benzophenone and bisphenolfluorene, respectively. The variation of the backbone structure affected the electronic properties, solubility, molecular weight and thermal stability of polyurethanes. The thermal stability of polyurethanes was studied by the gravimetric analyzer. The electrochromic performance was investigated by cyclic voltammograms and spectroelectrochemical methods, which showed stable and reversible electrochromic properties. Besides, the color of polyurethanes can be varied from initial colorless to green then to blue via electro-oxidation, which indicates the polyurethanes will have potential applications for eletrochromic materials. In addition, the PUs exhibited memory characteristic. The result indicated the PUs could be applied in smart window and memory devices.
- Ji, Yan,Zhang, Chunyu,Niu, Haijun,Zhao, Xiaofeng,Wang, Cheng,Qin, Chuanli,Wang, Wen,Bai, Xuduo
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p. 106 - 115
(2015/11/16)
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- Chemical linkage functions of poly(ether imide)s on the resistive switching memory effects
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A series of aromatic poly(ether imide)s, AZTA-PEIs containing triphenylamine and 1,2,4-triazole moieties are prepared and characterized. All the polymers with inherent viscosity from 0.58 to 1.1 dL/g show glass transition temperatures in the range of 250-278 °C. Resistive switching memory devices are constructed based on the processable poly(ether imide) (AZTA-PEIa). The device can be switched from the initial OFF state to the ON state under either positive or negative electrical sweep at about ±3.2 V. The ON state is nonvolatile and can maintain the high conducting state even turning off the electrical power and applying a reverse bias. The device fulfills the requirements of a write-once read-many times memory (WORM) with a high ON/OFF current ratio up to 105 and a long retention time in both ON and OFF states. The bistable switching effects of the polymer result from the conformation-coupled charge transfer from electron donors (triazole-substituted triphenylamine moieties) to electron acceptors (phthalimide moieties). By comparing with the memory behaviors of analogue polymers, the functions of ether and imide in the chemical polymer structure on the memory behaviors are discussed.
- Wang, Kun-Li,Shih, I.-Hao,Huang, Sheng-Tung,Tsai, Hsin-Luen
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p. 148 - 163
(2015/02/19)
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- New conjugated poly(pyridinium salt) derivative: AIE characteristics, the interaction with DNA and selective fluorescence enhancement induced by dsDNA
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Herein, a new conjugated poly(pyridinium salt) derivative L was synthesized by ring-transmutation polymerization reaction for the purpose of sensitive and selective fluorescence sensing of DNA. Cationic L exhibits aggregation-induced emission (AIE) characteristics that is weakly emissive in solution but highly luminescent in the aggregate state. Based on its AIE activity, a fluorescence turn-on biosensor for calf thymus DNA (ctDNA) detection is developed, which shows excellent selectivity with a detection limit down to the 10-8 M-1 in CH3CN-phosphate buffer solution (PBS) (2 mM, pH 7.4) (v/v 1: 1). Further, the interactions between L and ctDNA are carefully investigated by UV-vis absorption spectra, dynamic light scattering (DLS) measurements, thermal denaturation studies, circular dichroism (CD) measurements, as well as competing experiments with ethidium bromide (EB). More interestingly, L exhibits selective fluorescence enhancement induced by double-stranded DNA (dsDNA), therefore, L was also successfully utilized as fluorescent probe to follow the ctDNA cleavage process by bovine pancreatic deoxyribonuclease I (DNase I).
- Chang, Ying,Jin, Lu,Duan, Jingjing,Zhang, Qiang,Wang, Jing,Lu, Yan
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p. 103358 - 103364
(2015/12/23)
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- Electrosynthesis and electrochromic properties of poly(amide-triarylamine)s containing triptycene units
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Four bis(amide-triarylamine) derivatives featuring a triptycene as an interior core and terminal electroactive triphenylamine (TPA) or N-phenylcarbazole (NPC) groups were prepared by the condensation reactions from 1,4-bis(4-aminophenoxy)triptycene with 4-carboxytriphenylamine and N-(4-carboxyphenyl)carbazole, respectively, and from 1,4-bis(4-carboxyphenoxy)triptycene with 4-aminotriphenylamine and N-(4-aminophenyl)carbazole, respectively. The electrochemistry and electropolymerization of these bis(amide-triarylamine) derivatives were investigated. The stability of the oxidized forms of the bis(amide-triarylamine)s is affected by the orientation of amide linkage and the structure of terminal triarylamine unit. Two of the bis(amide-triarylamine)s could be electropolymerized into robust films on the electrode surface in an electrolyte solution. The electrogenerated polymer films exhibited reversible electrochemical oxidation processes and strong color changes upon electro-oxidation, which can be switched by potential modulation. The electrochromic properties of the films were evaluated by the spectroelectrochemical and electrochromic switching studies. The TPA-based film showed better electrochromic performance than the NPC-based one.
- Hsiao, Sheng-Huei,Chiu, Yu-Ting
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p. 90941 - 90951
(2015/11/11)
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- Catalytic carbon-nitrogen bond-forming cross-coupling using N-trimethylsilylamines
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Carbon-nitrogen bond-forming cross-coupling reaction of haloarenes with N-trimethylsilyl (TMS)-substituted secondary and primary arylamines proceeded with the aid of a palladium catalyst and a fluoride activator. Various TMS-N(aryl)2, TMS-NH(aryl), and TMS-N(alkyl)2 reacted to give the corresponding coupled products in high yields. Multi-TMS-amine nucleophiles such as N,N-(TMS)2-aniline and N,N′-Ph2-N,N′-(TMS)2-p-phenylenediamine also participated in this C-N coupling to give multiply C-N coupled products in high yields. The novel C-N cross-coupling reaction was successfully applied to C-N bond-forming polymerization. Relative rates of the cross-coupling of p-bromotoluene with N-TMS-substituted primary and secondary amines showed that N-TMS-diphenylamine reacted faster than N-TMS-N-methylaniline or N-TMS-aniline, and N-TMS-morpholine was the least reactive, indicating that the low basicity of the nitrogen nucleophile is the key for the smooth coupling.
- Minami, Yasunori,Komiyama, Takeshi,Shimizu, Kenta,Hiyama, Tamejiro,Goto, Osamu,Ikehira, Hideyuki
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p. 1437 - 1446
(2015/11/16)
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- C-N cross-coupling reaction catalysed by efficient and reusable CuO/SiO2 nanoparticles under ligand-free conditions
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Nanometric copper oxide supported on silica has been found to be a highly efficient and reusable catalyst for the C-N cross-coupling reaction of amines with aryl halides under ligand-free conditions. Various arylamines with different substituted groups can be synthesized in moderate to good yields. The catalyst can be recycled at least five times without obvious loss in catalytic activity.
- Hajipour, Abdol R.,Dordahan, Fatemeh,Rafiee, Fatemeh,Mahdavi, Mohammad
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p. 809 - 813
(2015/02/19)
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- Magnetically recyclable magnetite-palladium (Nanocat-Fe-Pd) nanocatalyst for the Buchwald-Hartwig reaction
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The immobilization of Pd on the magnetite surface afforded Nanocat-Fe-Pd using inexpensive precursors and its catalytic role in the Buchwald-Hartwig reaction for arylation of amines and amides was investigated; C-N bond formation was achieved in moderate to excellent yields and the catalyst could be separated and recycled up to five cycles by magnetic decantation without a significant loss in yield. This journal is the Partner Organisations 2014.
- Sa, Sofia,Gawande, Manoj B.,Velhinho, Alexandre,Veiga, Joao Pedro,Bundaleski, Nenad,Trigueiro, Joao,Tolstogouzov, Alexander,Teodoro, Orlando M. N. D.,Zboril, Radek,Varma, Rajender S.,Branco, Paula S.
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p. 3494 - 3500
(2014/07/08)
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- Small-molecule azomethines: Organic photovoltaics via Schiff base condensation chemistry
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Conjugated small-molecule azomethines for photovoltaic applications were prepared via Schiff base condensation chemistry. Bulk heterojunction (BHJ) devices exhibit efficiencies of 1.2% with MoOx as the hole-transporting layer. The versatility and simplicity of the chemistry is illustrated by preparing a photovoltaic device directly from the reaction mixture without any form of workup. This journal is the Partner Organisations 2014.
- Petrus,Bouwer,Lafont,Athanasopoulos,Greenham,Dingemans
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supporting information
p. 9474 - 9477
(2014/07/07)
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- Electron transfer and binding affinities in an electrochemically controlled ligand transfer system containing zinc porphyrin and a meso-phenylenediamine substituent
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Investigations on the transfer of the ligand, imidazole (HIm), between two covalently linked redox centres-zinc porphyrin and phenylenediamine (PD)-and the influence of the length of the linker are reported. Since the binding affinity of the ligand with zinc porphyrin is different from that of the ligand with the phenylenediamine moiety, the transfer of the ligand could be electrochemically controlled by adjusting the oxidation potentials. Changes in cyclic voltammograms and absorption spectra of the complexes revealed the site of ligand binding in the various oxidation states of the modified zinc porphyrins. Binding constants of the modified zinc porphyrins in various oxidation states were also determined by photometric titration with the ligand and digital simulations. Evidence for the delocalization of the electron from the zinc porphyrin to the phenylenediamine moiety and the influence of the delocalization on them were obtained from EPR studies. The Royal Society of Chemistry 2014.
- Cheng, Hsu Chun,Chen, Peter Ping Yu,Su, Yuhlong Oliver
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p. 1424 - 1433
(2014/01/06)
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- Synthesis and electrochromic properties of aromatic polyimides bearing pendent triphenylamine units
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A series of aromatic polyimides with pendent triphenylamine group were synthesized from equimolar mixtures of 4,4′-oxydianiline (ODA) and 4-(3,5-diaminobenzamido)triphenylamine (4), 4-(3,5-diaminobenzamido)-4′, 4″-di-tert-butyltriphenylamine (t-Bu-4) or 4-(3,5-diaminobenzamido)- 4′,4″-dimethoxytriphenylamine (MeO-4) with two aromatic tetracarboxylic dianhydrides (DSDA or 6FDA) via a conventional two-step procedure that included a ring-opening polyaddition to give poly(amic acid)s, followed by chemical imidization. These polyimides exhibited good solubility in polar organic solvents and could be solution-cast into flexible and strong films. They showed excellent thermal stability, with Tg values in the range of 284-309°C. The polyimides derived from diamines t-Bu-4 and MeO-4 exhibited reversible electrochemical oxidation, accompanied by strong color changes with high contrast ratio and electrochromic stability. For the polyimides derived from diamine 4, the coupling reaction between the triphenylamine radical cations occurred during the oxidative process forming a tetraphenylbenzidine structure, which resulted in an additional oxidation state and color change together with enhanced near-IR absorption at fully oxidized state.
- Hsiao, Sheng-Huei,Chou, Yu-Tan
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p. 2411 - 2421
(2014/05/20)
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- A simple and convenient method for the synthesis of N, N-diaryl tertiary amines
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Direct preparation of tertiary amines in which two substituents are aromatic is described. In the presence of either the inorganic base sodium tert-butoxide or the sterically hindered organic base diisopropylethylamine, the alkylation of secondary diarylamines is achieved smoothly. In contrast to methods previously reported in the literature, this procedure is high-yielding and does not require the use of transition-metal catalysts or functional-group-intolerant hydride reductants. Georg Thieme Verlag Stuttgart ? New York.
- Wekesa, Francis S.,Phadke, Neha,Jahier, Claire,Cordes, David B.,Findlater, Michael
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p. 1046 - 1051
(2014/05/06)
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- Silicon-based CN cross-coupling reaction
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Palladium-catalyzed CN bond-forming cross-coupling reaction of N-trimethylsilylamines with aryl bromides and chlorides is found to proceed in the presence of a fluoride activator in 1,3-dimethyl-2-imidazolidinone (DMI), giving triarylamines in excellent yields. When aryl bromide and bis(silyl)amine were used in this reaction, double CN bondforming products were obtained in high yields. The present reaction was successfully applied to CN bond-forming polymerization.
- Shimizu, Kenta,Minami, Yasunori,Goto, Osamu,Ikehira, Hideyuki,Hiyama, Tamejiro
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supporting information
p. 438 - 440
(2014/04/17)
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- Synthesis of tertiary aryl amines of various aryl halides and secondary amines using ortho-palladated complex of tribenzylamine
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The activity of dimeric [Pd{C6H4(CH 2N(CH2Ph)2)} (μ-Br)]2 complex as an efficient, air- and moisture-tolerant catalyst was investigated in amination reactions of various aryl halides with secondary amines. Substituted tertiary aryl amines were produced in excellent yields and short reaction times using catalytic amounts of this dimeric complex in DMSO at 120°C. Copyright
- Hajipour, Abdol R.,Dordahan, Fatemeh,Rafiee, Fatemeh
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p. 704 - 706
(2013/12/04)
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- Enhanced lifetime of organic light-emitting diodes using an anthracene derivative with high glass transition temperature
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Highly stable and efficient phosphorescent organic light-emitting diodes (OLEDs) were demonstrated by using anthracene-based hole injection buffer layer possessing high glass transition temperature. We synthesized a new anthracene derivative, 9,10-bis(3,3′-(N′,N′-diphenyl-(Nnaphthalene- 2-yl)benzene-1,4-diamine) phenyl)anthracene (TANPA) and characterized its optical and thermal properties. It showed high glass transition temperature of 154 °C which could be attributed to the insertion of anthracene into the aromatic amino group with triphenylamine. We also utilized TANPA for the hole injection and transport layers in phosphorescent OLEDs. Since TANPA has high glass transition temperature, the OLEDs using this material exhibited higher operational stability compared to the device without TANPA. When we use TANPA as the hole injection layer in combination with a widely-used hole transporting material, N,N′-di(1-naphthyl)-N,N-diphenylbenzidine (NPB), the devices showed high enhancement in terms of the operational lifetime, driving voltage change, and device efficiency, originating from the electron-hole charge balance as well as good thermal stability of TANPA. Copyright
- Lee, Seung-Hun,Kim, Sung Hyun,Kwak, Jeonghun
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p. 4216 - 4222
(2013/07/27)
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- Simple and convenient methods for N-arylation of heterocycles and diphenylamine
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N-Arylation of NH-heterocycles and diphenylamine with various aryl halides, using a readily accessible ligand-free potassium tert-butoxide/iron(III) oxide/dimethyl sulfoxide reagent system, gives the corresponding N-aryl derivatives in 47-97% yields. Georg Thieme Verlag Stuttgart . New York.
- Alakonda, Laxhmaiah,Periasamy, Mariappan
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experimental part
p. 1063 - 1068
(2012/05/04)
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- Synthesis and charge-discharge properties of a ferrocene-containing polytriphenylamine derivative as the cathode of a lithium ion battery
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In this work, a novel linear polytriphenylamine derivative was successfully synthesized by the introduction of ferrocene as a terminating group to the triphenylamine moieties. The morphology, structure and charge-discharge performance of the prepared polymer as the cathode were characterized by fourier transform infrared spectroscopy (FTIR), ultraviolet visible spectroscopy (UV-vis), scanning electron microscopy (SEM), cyclic voltammograms (CV) and galvanostatic charge-discharge testing. The results showed that the introduction of ferrocene to polytriphenylamine obviously improved the specific capacity and rate capability of the resulting PTPAFc cathodes in lithium ion batteries. Under our experimental conditions, the PTPAFc-based electrodes exhibited an initial discharge capacity of up to 100.2 mA h g-1 at 20 mA g -1 between 2.5 and 4.2 V, while PTPAn-based electrodes only presented 70.3 mA h g-1, comparatively. Also, the PTPAFc cathode specially retained over 89.7% of the initial capacity with a ten times increase of the current from 50 to 500 mA g-1. These improved electrochemical performances were ascribed to the introduction of ferrocene as the termination couple, which makes the PTPAFc main chain as a chainlike molecule structure and benefits from charge carrier transportation in the molecular polymer.
- Su, Chang,Ye, Yinpeng,Xu, Lihuan,Zhang, Cheng
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p. 22658 - 22662,5
(2020/09/15)
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- Monovalent nickel complex bearing a bulky N-heterocyclic carbene catalyzes buchwaldhartwig amination of aryl halides under mild conditions
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Monovalent nickel complex bearing a bulky N-heterocyclic carbene (NHC) and triphenylphosphine was synthesized and demonstrated to catalyze the BuchwaldHartwig amination of aryl halides with diarylamines to form triarylamines under mild conditions.
- Nagao, Shinya,Matsumoto, Taisuke,Koga, Yuji,Matsubara, Kouki
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supporting information; experimental part
p. 1036 - 1038
(2011/12/05)
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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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- Copolyfluorenes containing pendant bipolar groups: Synthesis, optoelectronic properties and applications
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This article reports the synthesis of copolyfluorenes (P1-P3) containing pendant bipolar groups (2.1-8.2 mol%), directly linked to hole-transporting triphenylamine and electron-transporting aromatic 1,2,4-triazole, by the Suzuki coupling reaction and their application in improving PLED performance of conventional MEH-PPV. The bipolar groups not only suppress undesirable green emission of polyfluorene under thermal annealing, but also promote electron- and hole-affinity of the resulting copolyfluorenes. Blending bipolar model compound M0 with MEH-PPV results in enhancement of device performance [ITO/PEDOT:PSS/M0 + MEH-PPV/Ca(50 nm)/Al(100 nm)]. Maximum luminance and luminance efficiency were increased from 3160 cd/m2 and 0.24 cd/A of MEH-PPV-only device to 6830 cd/m2 and 0.50 cd/A. Moreover, blending the bipolar copolyfluorenes with MEH-PPV further improves the device efficiency, with the maximum luminance and luminance efficiency being significantly enhanced up to 11090 cd/m2 and 0.56 cd/A (ca. 0.4 wt% of bipolar residue), respectively. Our results demonstrate the efficacy of the bipolar copolyfluorenes and model compound M0 in enhancing emission efficiency of MEH-PPV.
- Wu, Chia-Shing,Chen, Yun
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supporting information; scheme or table
p. 7700 - 7709
(2012/01/12)
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- Substituent effects on the redox properties and structure of substituted triphenylamines. An experimental and computational study
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The peak oxidation potentials of a series of polysubstituted triphenylamines were found to be highly linearly correlated (R=0.995) with their ionization potentials as computed by density functional theory. The computations, as well as confirming previous
- Wu, Xin,Davis, Anthony P.,Lambert, Peter C.,Kraig Steffen,Toy, Ozan,Fry, Albert J.
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experimental part
p. 2408 - 2414
(2009/07/18)
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- Novel anodic electrochromic aromatic polyamides with multi-stage oxidative coloring based on N,N,N′,N′-tetraphenyl-p-phenylenediamine derivatives
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A series of novel aromatic polyamides with pendent 4,4′-dimethoxy- substituted triphenylamine (TPA) units were prepared via the direct phosphorylation polycondensation from a new dicarboxylic acid monomer, N,N-bis(4-carboxyphenyl)-N′,N′-di(4-methoxyphenyl)-1, 4-phenylenediamine (4), and various aromatic diamines. These polyamides were amorphous with good solubility in many organic solvents, such as N-methyl-2-pyrrolidinone (NMP) and N,N-dimethylacetamide (DMAc), and could be solution-cast into flexible polymer films. They had excellent levels of thermal stability associated with their relatively high glass-transition temperatures (233-308 °C). These polymers exhibited strong UV-vis absorption bands at 351-363 nm in NMP solution. Their photoluminescence spectra showed maximum bands around 450-504 nm. The hole-transporting and electrochromic properties are examined by electrochemical and spectroelectrochemical methods. Cyclic voltammograms of the polyamide 6g prepared from the dicarboxylic acid monomer (4) with a structurally similar diamine monomer N,N-bis(4-aminophenyl)-N′, N′-di(4-methoxyphenyl)-1,4-phenylenediamine (5g) exhibited four reversible oxidation redox couples in acetonitrile solution at Eonset = 0.35, E1/2 = 0.64, 0.84, and 0.99 V, respectively. After over 3000 cyclic switches for green color, the films of polyamide 6g still showed excellent continuous cyclic stability of electrochromism.
- Chang, Cha-Wen,Liou, Guey-Sheng
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experimental part
p. 5638 - 5646
(2010/03/24)
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- Triaminophosphine ligands for carbon-nitrogen and carbon-carbon bond formation
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Methods and compounds are provided for the formation of carbon-nitrogen or carbon-carbon bonds comprising reacting an amine or an aryl boronic acid with an aryl halide in the presence of a palladium catalyst, a base, and a compound of formula II:
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Page/Page column 31-34; 35-36
(2008/12/05)
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- (t-Bu)2PN=P(i-BuNCH2CH2)3N: New efficient ligand for palladium-catalyzed C-N couplings of aryl and heteroaryl bromides and chlorides and for vinyl bromides at room temperature
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(Chemical Equation Presented) By employing Pd(OAc)2, Cs 2CO3, or NaOH, and the new ligand (t-Bu) 2PN=P(i-BuNCH2CH2)3N (3a), an electronically diverse array of aryl bromides and chlorides possessing base-sensitive substituents (nitro, ester, and keto) provide coupling products with bulky aryl amines in good to excellent yields. Aryl halides possessing other functional groups including cyano, amino, trifluoromethyl, and phenol, coupled with equal ease, producing highly functionalized amines in good to excellent yields. Moreover, an aryl chloro group can be preserved in the presence of a bromo substituent under our reaction conditions. BOC-protected amines also participated efficiently. Heterocyclic bromides and chlorides underwent clean couplings with amines in excellent yields. An important strength of our protocol is the use of lower palladium loadings than those reported earlier, without compromising yields. The air-stable palladium complex (η3-cinnamyl)PdCl·(3a) (5) was also employed successfully in C-N coupling reactions while the crotyl analogue was less efficacious. The 3a/Pd(OAc)2 catalyst system promotes, for the first time, efficient coupling of vinyl bromides with a variety of amines to produce imines and enamines at room temperature.
- Reddy, Ch. Venkat,Kingston, Jesudoss V.,Verkade, John G.
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p. 3047 - 3062
(2008/09/19)
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- N-Arylation of aliphatic, aromatic and heteroaromatic amines catalyzed by copper bis(2,2,6,6-tetramethyl-3,5-heptanedionate)
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Copper bis(2,2,6,6-tetramethyl-3,5-heptanedionate) was found to be an efficient catalyst for N-arylation of aliphatic, aromatic and heteroaromatic amines with aryl iodides/bromides under mild conditions. The system tolerated a variety of hindered and functionalized amines/aryl halides and the desired N-aryl amines were obtained in good to excellent yields.
- Nandurkar, Nitin S.,Bhanushali, Mayur J.,Bhor, Malhari D.,Bhanage, Bhalchandra M.
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p. 6573 - 6576
(2008/02/12)
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- AROMATIC AMINE COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE USING SAME
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Disclosed is an aromatic amine compound of a specific structure having at least one fluorene structure represented by the formula (1) below. Also disclosed is an organic electroluminescent device wherein an organic thin film composed of one or more layers including at least a light-emitting layer is interposed between a cathode and an anode and at least one layer in the organic thin film contains the aromatic amine compound by itself or as a component of a mixture. Such an organic electroluminescent device has various luminescent hues, high heat resistance, long life, high luminance and high luminous efficiency. The above-mentioned novel aromatic amine compound enables to realize such an organic electroluminescent device. (In the formula below, Ar1-Ar6 independently represent a substituted or unsubstituted aryl group having 5-60 nuclear carbon atoms or the like, and L1-L3 independently represent a substituted or unsubstituted arylene group having 5-60 nuclear carbon atoms or the like.)
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Page/Page column 71
(2008/06/13)
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- Facile N-arylation of amines and sulfonamides and O-arylation of phenols and arenecarboxylic acids
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An efficient, transition-metal-free procedure for the N-arylation of amines, sulfonamides, and carbamates and O-arylation of phenols and carboxylic acids has been achieved by allowing these substrates to react with a variety of o-silylaryl inflates in the presence of CsF. Good to excellent yields of arylated products are obtained under very mild reaction conditions. This chemistry readily tolerates a variety of functional groups.
- Liu, Zhijian,Larock, Richard C.
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p. 3198 - 3209
(2007/10/03)
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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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- 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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p. 411 - 414
(2007/10/03)
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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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p. 307 - 316
(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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