- 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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- 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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- 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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- Organic dyes containing nonsubstituted aryl amino moieties and azobenzene units for dye-sensitized solar cells
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A series of novel sensitizers were successfully synthesized utilizing azobenzene as a π-linkage unit for the D–π–A structure. A slight red shift on the absorption spectra and λonset of the sensitizers could be observed when the thienyl group was introduced to the acceptor moiety (A). In addition, replacing the donor moiety (D) from carbazole to diarylamino could lead to a negative shift (approximately 0.3 V) in the first oxidation potential. DFT calculation was also carried out and the trend of calculated HOMO–LUMO gaps was consistent to the experimental data obtained from the CV results (DT1 DT2 DT3 DT4). These sensitizers were then employed in dye-sensitized solar cells to investigate their photovoltaic performances. Highest power conversion efficiency (PCE) of 0.84% was achieved for DT1-based DSSC according to its most bathochromic absorption spectrum.
- Toan, Nguyen Duc,Chiu, Kuo Yuan,Tran, Thai Thi Ha,Yang, Te-Fang,Su, Yuhlong Oliver
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- Conjugated donor-acceptor-acceptor (D-A-A) molecule for organic nonvolatile resistor memory
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A new donor-acceptor-acceptor (D-A-A) type of conjugated molecule, N-(4-(N′,N′-diphenyl)phenylamine)-4-(4′-(2,2-dicyanovinyl)phenyl) naphthalene-1,8-dicarboxylic monoimide (TPA-NI-DCN), consisting of triphenylamine (TPA) donors and naphthalimide (NI)/dicyanovinylene (DCN) acceptors was synthesized and characterized. In conjunction with previously reported D-A based materials, the additional DCN moiety attached as end group in the D-A-A configuration can result in a stable charge transfer (CT) and charge-separated state to maintain the ON state current. The vacuum-deposited TPA-NI-DCN device fabricated as an active memory layer was demonstrated to exhibit writeonce- read-many (WORM) switching characteristics of organic nonvolatile memory due to the strong polarity of the TPA-NI-DCN moiety.
- Dong, Lei,Li, Guangwu,Yu, An-Dih,Bo, Zhishan,Liu, Cheng-Liang,Chen, Wen-Chang
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- Near-Infrared Boron Difluoride Formazanate Dyes
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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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- 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
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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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- 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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- Azobenzene-based Organic Dyes, Preparation Method Thereof, and Dye-sensitized Solar Cells Comprising the Same
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An organic dye based on azobenzene (1) represented by chemical formula (azobenzene), a method for preparing the same, and a dye-sensitized solar cell using the same are D, π-A, (1), and 1 (D) in the formula (donor): (R). 1 ) (R)2 ) N - Where it is R. 1 And R2 Is independently hydrogen, a halogen element, a substituted or unsubstituted C1?C20 alkyl, a substituted or unsubstituted C1?C20 alkoxy, a substituted or unsubstituted C4?C10 aryl, or a substituted or unsubstituted C3?C10 heteroaryl. Π (π spacer) is - π1 -(Π)2 )n -Π-π. 1 is possible. A photoisomerization group represented by the formula, wherein the R is the same as defined above. 3 And R4 Is independently hydrogen, a halogen element, a substituted or unsubstituted C1?C4 alkyl, or a substituted or unsubstituted C1?C4 alkoxy. Π π2 is possible. , Where n is R. 5 Is hydrogen, a halogen element, a substituted or unsubstituted C1?C4 alkyl, or a substituted or unsubstituted C1?C4 alkoxy. Here n is a natural number of 0 or 1; FIGS. A (acceptor) Is an anchoring group (Anchoring group); FIGS. The substituent is at least one selected from the group consisting of halogen elements, hydroxy, C1?C3 alkyl, and C1?C3 alkoxy. The hetero atom is at least one selected from the group consisting N, O and S.
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Paragraph 0141-0142; 0148-0150
(2021/10/05)
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- Triphenylamine/carbazole-modified ruthenium(ii) Schiff base compounds: Synthesis, biological activity and organelle targeting
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Four triphenylamine/carbazole-modified half-sandwich ruthenium(ii) compounds [(η6-p-cymene)Ru(N/O^N)Cl]0/+ with Schiff base chelating ligands (N/O^N) are synthesized and characterized. The introduction of Schiff base units effectively increases the antitumor activity of these compounds (IC50: 1.70 ± 0.56-17.75 ± 3.10 μM), which, meanwhile, can inhibit the metastasis of tumor cells effectively. These compounds follow an energy-dependent cellular uptake mechanism, mainly accumulate in lysosomes to destroy their integrity, and then eventually promote apoptosis. In addition, these compounds can induce an increase of intracellular reactive oxygen species (ROS) levels and provide an antitumor mechanism of oxidation, which is confirmed by the decrease of mitochondrial membrane potential (MMP) and the catalytic oxidation of the coenzyme nicotinamide-adenine dinucleotide (NADH). All these indicate that these ruthenium(ii) compounds are expected to be dual-functional antitumor agents: anti-metastasis and lysosomal damage.
- Chen, Shujiao,Ge, Xingxing,Huang, Jie,Liu, Tong,Liu, Xicheng,Liu, Zhe,Shao, Yue,Tian, Laijin,Wang, Qinghui,Yao, Meimei,Yuan, Xiang-Ai
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supporting information
p. 8774 - 8784
(2020/07/10)
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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.
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- Charge-transporting paint
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A charge-transporting varnish including charge-transporting material comprising N,N'-diaryl benzidine derivatives represented by formula (1), a charge-accepting dopant comprising heteropoly acid, and an organic solvent. [In the formula, R 1 to R 8 independently represent hydrogen, a halogen, an alkyl having 1 to 20 carbon atoms, an alkenyl having 2 to 20 carbon atoms or an alkynyl having 2 to 20 carbon atoms; and Ar 1 and Ar 2 independently represent groups represented by formulas (2) or (3). (In the formula, R 9 to R 18 independently represent hydrogen, a halogen, an alkyl having 1 to 20 carbon atoms, an alkenyl having 2 to 20 carbon atoms or an alkynyl having 2 to 20 carbon atoms; and X 1 and X 2 independently represent hydrogen, a halogen, an alkyl having 1 to 20 carbon atoms, an alkenyl having 2 to 20 carbon atoms, an alkynyl having 2 to 20 carbon atoms, diphenylamino, 1-naphthylphenylamino, 2-naphthylphenylamino, di(1-naphthyl)-amino, and di(2-naphthyl)-amino or 1-naphthyl-2-naphtylamino.)]
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Paragraph 0079; 0080
(2018/06/21)
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- Catalyst-Directed Chemoselective Double Amination of Bromo-chloro(hetero)arenes: A Synthetic Route toward Advanced Amino-aniline Intermediates
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A chemoselective sequential one-pot coupling protocol was developed for preparing several amino-anilines in high yield as building blocks for active pharmaceutical ingredients (APIs). Site (Cl vs Br on electrophile) and nucleophile (amine vs imine) selectivity is dictated by the catalyst employed. A Pd-crotyl(t-BuXPhos) precatalyst selectively coupled the Ar-Br of the polyhaloarene with benzophenone imine, even in the presence of a secondary amine, while Pd-based RuPhos or (BINAP)Pd(allyl)Cl coupled the Ar-Cl site with secondary amines.
- Mikhailine, Alexandre A.,Grasa Mannino, Gabriela A.,Colacot, Thomas J.
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p. 2301 - 2305
(2018/04/30)
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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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- Grafting triphenylamine groups onto polysiloxanes to improve interaction between the electrochromic films and ITO
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A novel series of triphenylamine (TPA)-contained polysiloxanes (PTPASi) have been synthesized by a normal reaction of hydrosilylation through poly(methylhydrosiloxane)(PMHS) with four TPA-based alkenes (TPAA) for electrochromic applications. Grafting TPA onto polysiloxanes was employed as a strategy to ameliorate the thermal stability and cycle stability of the electrochromic properties due to the enhanced force of adhesion between the polymer films and the ITO substrate. The morphology and impedance of the polymers after electro-oxidizing reaction was studied and didn't reveal significant change suggesting good stability of the hybrid system. Meanwhile, with the introducing of the polysiloxane backbones, the four polymer films appeared nearly colorless in their natural state, in contrast to three primary colors of red, green and blue in their oxidized state. Hence, these PMHS films can be mixed to obtain all the other colors on the basis of the color mixing theory. In addition, the potential switching properties of the four polymers at the temperature of 150?°C have been investigated for the first time, which indicate high thermal stability and potential for relatively high temperature and/or long term cycling applications.
- Hao, Liping,Wang, Wen,Niu, Haijun,Zhou, Yu
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p. 259 - 268
(2017/06/19)
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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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- ANILINE DERIVATIVE, CHARGE-TRANSPORTING VARNISH AND ORGANIC ELECTROLUMINESCENT DEVICE
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Provided is an aniline derivative represented by formula (1). (In formula (1), R 1 represents an alkyl group, an alkenyl group, an alkynyl group, an aryl group having 6-20 carbon atoms, a heteroaryl group, or a group represented by formula (2), and R 2 -R 55 independently represent a hydrogen atom, a halogen atom, a nitro group, a cyano group, an aldehyde group, a hydroxy group, a thiol group, a carboxylic acid group, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, etc.)
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Paragraph 0214; 0215; 0216; 0217; 0218
(2016/10/17)
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- Diazene sulphonate as a cross-linking agent for polymers with pendant triarylamine hole-conducting units
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Diazene sulphonates are readily available compounds which are soluble in water and polar solvents. They strongly absorb the UV-VIS light and they decompose under UV irradiation via radical or ionic intermediates. These properties render them valuable, e.g. for analytical purposes and for photo-printing. In this presentation, it will be demonstrated that polymers with a pendant diazene sulphonate function as cross-linking agents and with pendant aromatic amines as hole-transporters can be considered as useful materials for organic light-emitting device (OLED) technology.
- Baranovicova, Eva,Stasko, Andrej,Nuyken, Oskar
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p. 1238 - 1252
(2016/07/06)
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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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- Schiff bases containing triphenylamine and pyrrole units: Synthesis and electrochromic, acidochromic properties
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Five Schiff bases (SBs) containing pyrrole and different triphenylamine (TPA) moieties were synthesized and the structures were confirmed by infrared spectroscopy (IR) and the nuclear magnetic resonance (NMR) technique. SB1 exhibited intense fluorescence emission in contrast to SB2-SB5. The electrochemical behaviors of the SBs were investigated by the cyclic voltammetry (CV) technique. SB2-SB5 exhibited redox stability with one well-defined and reversible redox couple upon electrochemical oxidation. On the contrary, SB1 revealed two oxidation peaks and one reduction peak in the first CV curve, followed by four well-defined redox couples in the steady-state CV curves. Electrochromic behaviors of the SBs have been observed, accompanied with a new absorption peak appearing with obvious color change from pale yellow neutral form to red oxidation form. SB1-SB5 also displayed sensitive acidochromic behaviors, and a linear dependence of maximum absorption wavelength as a function of pH values has been observed which proved the SBs could be used as alternative pH sensors in the given range.
- Li, Yu,Zhang, Yanhong,Niu, Haijun,Wang, Cheng,Qin, Chuanli,Bai, Xuduo,Wang, Wen
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p. 5245 - 5254
(2016/07/06)
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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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- 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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- 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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- 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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- 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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- NOVEL ORGANIC ELECTROLUMINESCENT COMPOUNDS AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME
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Provided are novel organic electroluminescent compounds and an organic electroluminescent device using the same. Because the organic electroluminescent device using the organic electroluminescent compound as a hole transport material or a hole injection material exhibits good luminous efficiency and excellent lifetime properties, it is used to manufacture OLED devices having superior operating lifetime and consuming less power due to improved power efficiency.
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Page/Page column 21-22
(2012/02/13)
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- NOVEL CATALYSTS
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The present invention provides novel compounds and ligands that are useful in transition metal catalyzed cross-coupling reactions. For example, the compounds and ligands of the present invention are useful in palladium or gold catalyzed cross-coupling reactions.
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Page/Page column 61-62
(2012/06/01)
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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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- 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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p. 4487 - 4497
(2012/05/20)
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- Bipolar copoly(aryl ether) containing distyrylbenzene, triphenylamine, and 1,2,4-triazole moieties: Synthesis and optoelectronic properties
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A novel copoly(aryl ether) (P1) consisting of alternate emitting segments (distyrylbenzene) and a bipolar moiety composed of directly linked electron-transporting aromatic 1,2,4-triazole and hole-transporting triphenylamine was synthesized. The copoly(aryl ether) is readily soluble in common organic solvents and exhibit good thermal stability with thermal decomposition temperature above 450 °C. The emission and the photoluminescence quantum yield of the copolymer are dominated by the emitting segments (distyrylbenzene) with longer emissive wavelength. Electron affinity of P1 is evidently enhanced after introducing the isolated bipolar unit, as confirmed by the lowered lowest unoccupied molecular orbital level (-2.77 eV) relative to P0 without bipolar unit (-2.34 eV). This results in improved emission efficiency of its polymer light-emitting diode (indium tin oxide/poly(3,4-ethylene dioxythiophene):poly(styrene sulfonate)/P1/LiF/Ca/Al) due to more balanced charges injection and transport. Blending P1 with poly(9,9-dihexylfluorene) (PF) further improves the efficiency of the device; the best performance was obtained for PF/P1 = 20/0.8 (w/w) with maximum luminance and maximum luminance efficiency being significantly enhanced to 3260 cd/m2 and 1.08 cd/A, respectively, from 380 cd/m2 and 0.009 cd/A of P1-based device. These results demonstrate that the bipolar moiety can be used to enhance charges injection and transport of electroluminescent polymers.
- Wu, Chia-Shing,Lee, Shawn-Lin,Chen, Yun
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scheme or table
p. 3099 - 3108
(2012/05/05)
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- A P,N-Ligand for palladium-catalyzed ammonia arylation: Coupling of deactivated aryl chlorides, chemoselective arylations, and room temperature reactions
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(Figure Presented) Amazing ammonia: A new air-stable P,N-ligand (Mor-DalPhos) is reported that enables the palladium-catalyzed crosscoupling of ammonia to a variety of aryl chloride and aryl tosylate substrates with high chemoselectivity and, for the first time, at room temperature (see scheme; Ad = adamantyl, Ts=para-toluenesulfonyl).
- Lundgren, Rylan J.,Peters, Brendan D.,Alsabeh, Pamela G.,Stradiotto, Mark
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supporting information; experimental part
p. 4071 - 4074
(2010/07/05)
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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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p. 7700 - 7709
(2012/01/12)
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- FLUORESCENT AROMATIC SENSORS AND THEIR METHODS OF USE
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Aromatic molecules that can be used as sensors are described. The aromatic sensors include a polycyclic aromatic hydrocarbon core with a five-membered imide rings fused to the core and at least two pendant aryl groups. The aromatic sensor molecules can detect target analytes or molecular strain as a result of changes in their fluorescence, in many cases with on-off behavior. Aromatic molecules that fluoresce at various frequencies can be prepared by altering the structure of the aromatic core or the substituents attached to it. The aromatic molecules can be used as sensors for various applications such as, for example, the detection of dangerous chemicals, biomedical diagnosis, and the detection of damage or strain in composite materials. Methods of preparing aromatic sensor molecules are also described.
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Page/Page column 14
(2008/12/07)
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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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- 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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- 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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- 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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- 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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