- Synthesis and photophysical properties of triphenylamine-based dendrimers with 1,3,5-triphenylbenzene cores
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Two new conjugated dendrimers bearing a triphenylamine moiety as dendrons and 1,3,5-triphenylbenzene as a core have been synthesized through a convergent synthetic strategy. These conjugated dendrimers have high fluorescence quantum yields and exhibit similar absorption and emission behaviors in solutions and in solid films, which demonstrate that these dendrimers form good amorphous states.
- Xia, Haijian,He, Jiating,Peng, Ping,Zhou, Yinhua,Li, Yaowen,Tian, Wenjing
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- A tetraphenylmethane based starburst triarylamine cluster: Spectroscopy, electrochemistry and morphological studies
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While tetraphenylmethane and triphenylamine are crystalline molecules, a starburst hybrid of the two leads to a low band-gap molecular glass which retains the optical and electrochemical properties of the individual components.
- Sengupta, Saumitra,Sadhukhan, Subir Kumar,Muhuri, Sanjukta
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- Piezofluorochromism of triphenylamine-based triphenylacrylonitrile derivative with intramolecular charge transfer and aggregation-induced emission characteristics
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New triphenylacrylonitrile derivative (DPPA) with triphenylamine moiety as electron donor group has been synthesized. Its emission wavelengths were strongly affected by solvent polarity, indicating intramolecular charge transfer (ICT) transitions. It was found that DPPA was almost non-emissive in tetrahydrofuran (THF), and the emission could be intensified obviously when a great amount of H2O was added, illustrating aggregation induced emission property. It is interesting that the pristine crystal of DPPA emitted green light, and the ground made its emitting color to change into orange, which could be recovered under fumed with dichloromethane (DCM) vapor. The piezofluorochromic behavior might be switched reversibly under the stimulus of external force because of crystalline-amorphous phase transformation, which could be confirmed from the results of PXRD patterns and DSC curves in different solid states. This work might open a new strategy to provide a broad perspective for the development of AIE PFC materials.
- Wang, Xin,Wang, Yunhan,Zhan, Yong,Yang, Peng,Zhang, Xiaojing,Xu, Yongnan
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- A triphenylamine-capped solution-processable wholly aromatic organic molecule with electrochemical stability and its potential application in photovoltaic devices
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A triphenylamine-capped solution-processable wholly aromatic conjugated molecule, TPA-TVBP, was designed and synthesized. It exhibited a high thermodynamic stability and good film forming ability as expected, originating from the absence of alkyl and alkoxyl moieties. The triphenylamine cap provided a good solubility because of three-dimensional propeller structure and a donor moiety to construct the organic D-π-A molecule with the electron-deficient tribenzo[a,c,i]phenazine moiety as the acceptor. The special electrochemical stability was discussed through cyclic voltammetry and potential switching step measurements, and the photocurrent generation in photovoltaic device application was described further. Simple bulk heterojunction photovoltaic cells were fabricated using TPA-TVBP and PCBM, and the higher short circuit current and fill factor than the similar structures were achieved. Based on the mechanism of the photocurrent generation, the TPA-TVBP molecule would be a good model molecule to investigate the electrochemical properties of the triphenylamine-capped material in photovoltaic device application.
- Wang, Zhiming,Song, Xiaohui,Ma, Lingling,Feng, Ying,Gu, Cheng,Zhang, Xiaojuan,Lu, Ping,Ma, Yuguang
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- Photorefractive response of polymeric composites with pendant triphenylamine moiety
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The photorefractive property of newly synthesized polymeric composite, poly(4-diphenylamino)styrene (PDAS), as a triphenylamine pendant moiety is analyzed. The photorefractive performance of PADS composites including a sensitizer, a nonlinear optical dye and a plasticizer was also investigated. Photorefractive organic composites have the high potential applications such as holographic optical devices for data storage and real-time image processing. Large symmetric two-beam coupling, which is caused by out-of-phase refractive index modulation with respect to illumination pattern, is a unique feature of photorefractive materials.
- Tsutsumi, Naoto,Murao, Takehiro,Sakai, Wataru
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- Synthesis and properties of twin derivatives of triphenylamine and carbazole
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Synthesis as well as thermal, optical, photophysical, and electrochemical properties of new carbazole and triphenylamine twin derivatives with high triplet energies are reported. The synthesized compounds exhibit ability of glass formation. Their glass transition temperatures are in the range of 32–37?°C. The triphenylamine and carbazole derivatives absorb electromagnetic irradiation in the range of 200–360?nm with the band gaps of 3.71 and 3.44?eV, respectively. DFT calculations show that HOMO and LUMO orbitals of compounds are localized separately on the substituents and central 4,4′-thiodibenzenthiol unit, respectively. The synthesized twin derivatives have triplet energies of 2.72 and 2.76?eV. The electron photoemission spectra of the films of the synthesized compounds reveal ionization potentials of 5.54 and 5.61?eV.
- Simkus,Tomkeviciene,Volyniuk,Mimaite,Sini,Budreckiene,Grazulevicius
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- Synthesis, characterization, two-photon absorption, and optical limiting properties of triphenylamine-based dendrimers
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Three π-conjugated dendrimers (Ph-G0, Ph-G1 and Ph-G2) bearing triphenylamine moieties have been synthesized through a convergent synthetic strategy without any protection-deprotection chemistry. The linear photophysical properties, two-photon absorption (TPA), and optical limiting behavior of the dendrimers were investigated in solution at room temperature. Linear absorption and emission spectra revealed a bathochromic shift and decreased fluorescence quantum yields with increasing dendrimer generation. A strong cooperative effect in the TPA absorption of these dendrimers was observed. The TPA cross-sections increase gradually with the proportion of triphenylamine units and the maximum value of the TPA cross-section can reach 5690 GM for Ph-G2. These triphenylamine-based dendrimers exhibited efficient two-photon optical limiting under femtosecond excitation.
- Xu, Bin,Fang, Honghua,Chen, Feipeng,Lu, Hongguang,He, Jiating,Li, Yaowen,Chen, Qidai,Sun, Hongbo,Tian, Wenjing
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- Ultra-fast co-sensitization and tri-sensitization of dye-sensitized solar cells with N719, SQ1 and triarylamine dyes
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This paper describes the synthesis of a new, yellow triphenylamine dye, 4-[2-(4-diphenylaminophenyl)vinyl]benzoic acid] (6), with a sorption maximum at 380 nm in solution for which EQE data show shifts to 420 nm on sorption to TiO2. The performance of this dye has been measured in dye-sensitized solar cell (DSC) devices, showing η = 2.6% for 1 cm2 devices. Light soaking of (6) shows excellent long-term stability with 2 photo-electrodes in 5 minutes using one or two dyes and the first example of ultra-fast tri-sensitization. The dyes tested include the ruthenium dye N719, the squaraine dye SQ1, the red triphenylamine dye 2-cyano-3-{4-[2-(4-diphenylaminophenyl) vinyl]phenyl}acrylic acid (5) and (6). DSC efficiencies of 7.5% have been achieved for 1 cm2 devices co-sensitized using (6) and N719. These efficiencies exceed those recorded for single dye devices and EQE measurements confirm efficient photon capture from two or more dyes in a single photo-electrode. Photo-acoustic calorimetry (PAC) has also been used to measure the energy of the charge separation states formed for (6) and N719, showing a larger value (1.47 eV) for (6) compared to N719 (1.08 eV), whilst a TiO 2 film co-sensitized with both (6) and N719 gave an intermediate value (1.28 eV). These data have been used to calculate dye HOMO, LUMO and λmax levels for (6) and N719 leading to important insights for future successful co-sensitization.
- Holliman, Peter J.,Mohsen, Moneer,Connell, Arthur,Davies, Matthew L.,Al-Salihi, Kareem,Pitak, Mateusz B.,Tizzard, Graham J.,Coles, Simon J.,Harrington, Ross W.,Clegg, William,Serpa, Carlos,Fontes, Octavio H.,Charbonneau, Cecile,Carnie, Matthew J.
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- An octupolar near-IR dye with triphenylamine donors: Preparation and absorption properties
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A topologically new NIR dye based on a carbocation centered octupole and conjugated triphenylamine donors is described. The dye produced an absorption maximum at 954 nm and by virtue of its two degenerate NBMO-LUMO transitions, showed a large molar extinction coefficient (log ε 4.9).
- Sengupta, Saumitra
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- Nanostructures of n-type organic semiconductor in a p-type matrix via self-assembly of block copolymers
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The block copolymerization of 4-vinyltriphenylamine and a perylene bisimide acrylate was analyzed using a nitroxide-mediated living radical polymerization. The functionalized block copolymer consists of one block with a hole transport moiety and second block with an electron transport moiety with light absorption properties. It was observed that the polymers show phase separation with increasing amounts of dye that build up in nanostructures of perylene bisimide in a PvTPA matrix over a large area. The formation of n-type organic semiconductor in a polymer matrix opens up new concept in nanoscience and molecular electronics.
- Lindner, Stefan M.,Thelakkat, Mukundan
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- (DiMeIHeptCl)Pd: A Low-Load Catalyst for Solvent-Free (Melt) Amination
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(DiMeIHeptCl)Pd, a hyper-branched N-aryl Pd NHC catalyst, has been shown to be efficient at performing amine arylation reactions in solvent-free ("melt") conditions. The highly lipophilic environment of the alkyl chains flanking the Pd center serves as lubricant to allow the complex to navigate through the paste-like environment of these mixtures. The protocol can be used on a multi-gram scale to make a variety of aniline derivatives, including substrates containing alcohol moieties.
- Semeniuchenko, Volodymyr,Sharif, Sepideh,Day, Jonathan,Chandrasoma, Nalin,Pietro, William J.,Manthorpe, Jeffrey,Braje, Wilfried M.,Organ, Michael G.
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p. 10343 - 10359
(2021/07/31)
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- Fluorescent dye
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To provide a fluorescent dye having higher fluorescence intensity.SOLUTION: A fluorescent dye comprises a triazole condensed ring compound represented by general formula (I). In the general formula (I), R1, R2 independently represent a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group; A1 is at least one functional group selected from the group consisting of -(CH=CRa)n- (n is an integer of 1-6), -(CH2)n- (n is an integer of 1-6), -(AO)n- (AO is a C2-6 alkylene oxide, n is an integer of 1-10), -NHCOO-, -CONH-, -CONH(Rb)-, -COO-, -SO2 NH-, -HN-C(=NH)-NH-, -O-, -S-, -NRb-, -Ar- (Ar is an aryl group or a heteroaryl group), -CO-Ar-NRb-; Ra is a hydrogen atom or a C1-4 alkyl group; Rb is a C1-4 alkyl group; B1 is an alkyl ester group, an alkyl ether group, an alkyl amide group, or a (C2-6) alkylene oxide adduct thereof, or a reactive group with a biomolecule optionally having a linking group to A1.SELECTED DRAWING: None
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Paragraph 0131-0133
(2021/03/13)
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- Copper-Catalyzed Transfer Hydrodeuteration of Aryl Alkenes with Quantitative Isotopomer Purity Analysis by Molecular Rotational Resonance Spectroscopy
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A copper-catalyzed alkene transfer hydrodeuteration reaction that selectively incorporates one hydrogen and one deuterium atom across an aryl alkene is described. The transfer hydrodeuteration protocol is selective across a variety of internal and terminal alkenes and is also demonstrated on an alkene-containing complex natural product analog. Beyond using 1H, 2H, and 13C NMR analysis to measure reaction selectivity, six transfer hydrodeuteration products were analyzed by molecular rotational resonance (MRR) spectroscopy. The application of MRR spectroscopy to the analysis of isotopic impurities in deuteration chemistry is further explored through a measurement methodology that is compatible with high-throughput sample analysis. In the first step, the MRR spectroscopy signatures of all isotopic variants accessible in the reaction chemistry are analyzed using a broadband chirped-pulse Fourier transform microwave spectrometer. With the signatures in hand, measurement scripts are created to quantitatively analyze the sample composition using a commercial cavity enhanced MRR spectrometer. The sample consumption is below 10 mg with analysis times on the order of 10 min using this instrument - both representing order-of-magnitude reduction compared to broadband MRR spectroscopy. To date, these measurements represent the most precise spectroscopic determination of selectivity in a transfer hydrodeuteration reaction and confirm that product regioselectivity ratios of >140:1 are achievable under this mild protocol.
- Alansari, Isabella Y.,Clark, Joseph R.,Holdren, Martin S.,Neill, Justin L.,Pate, Brooks H.,Reyes, Albert,Sloane, Samantha E.,Sonstrom, Reilly E.,Vang, Zoua Pa
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supporting information
p. 7707 - 7718
(2021/06/21)
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- Deep imaging for visualizing nitric oxide in lipid droplets: discovering the relationship between nitric oxide and resistance to cancer chemotherapy drugs
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A near-infrared two-photon fluorescent probe (TAN) was synthesized for selective detection and deep-depth imaging of NO in lipid droplets. All results demonstrated that NO production in lipid droplets is closely correlated with the resistance to anti-tumor drugs, and NO inhibitors can effectively improve the efficacy of chemotherapeutic agents.
- He, Meng,Hu, Wei,Li, Chenchen,Li, Chunya,Liu, Zhihong,Wang, Yanying,Ye, Miantai,Zhai, Shuyang,Zhang, Huijuan
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p. 6233 - 6236
(2020/06/22)
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- Aromatic pyridazine compound as well as preparation method and application thereof (by machine translation)
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The invention discloses an aromatic pyridazine compound and a use thereof. 1 H-NMR and the like are characterized in that the compound has a longer charge-off-state life and can be used as a better photoelectric material. In addition, the invention further provides a preparation method of the aromatic pyridazine compound, and the preparation method is environment-friendly and convenient to operate. The method comprises the following steps: Step 1, reacting 2 and 4 - dibromonitrobenzene as raw materials through coupling reaction, 5, 5 - dibromo -2, 2 ’ -dinitrobiphenyl, step 2 and taking R1 The substituted ethylene derivatives and 5, 5 - dibromo -2 and 2 ’ -dinitrobiphenyl serve as raw materials to synthesize nitro-substituted compounds through coupling reaction; step 3: synthesizing an aromatic pyridazine compound by a reduction reaction with the nitro-substituted compound as a raw material. The invention further discloses application of the aromatic pyridazine compound in a solar cell and application of the aromatic pyridazine compound in pH detection. (by machine translation)
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- Polymer, and mixture or formulation, and organic electronic device containing same, and monomer thereof
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Disclosed are a polymer, and a mixture or a formulation and an organic electronic device containing same, and applications thereof, and further a monomer of which the polymer is made; the polymer comprises on its side chain a repeating structure unit E, characterizing in that its S1(E)?T1(E))≤0.35 eV or even less, which may allow the said polymer having thermally activated delayed fluorescence (TADF) property. Thus a TADF polymer suitable for printing processes is provided, thereby reducing OLED manufacturing costs.
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Page/Page column 53; 54; 61-62
(2020/11/23)
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- Visible-Light-Induced Pd-Catalyzed Radical Strategy for Constructing C-Vinyl Glycosides
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A novel visible-light-induced palladium-catalyzed Heck reaction for bromine sugars and aryl olefins with high regio- and stereochemistry selectivity for the preparation of C-glycosyl styrene is described. This reaction takes place in one step at room temperature by using a simple and readily available starting material. This protocol can be scaled up to a wide range of glycosyl bromide donors and aryl olefin substrates. Mechanistic studies indicate that a radical addition pathway is involved.
- Li, Ming,Qiu, Yi-Feng,Wang, Cui-Tian,Li, Xue-Song,Wei, Wan-Xu,Wang, Yu-Zhao,Bao, Qiao-Fei,Ding, Ya-Nan,Shi, Wei-Yu,Liang, Yong-Min
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supporting information
p. 6288 - 6293
(2020/09/02)
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- A [...] reagent catalytic synthesis method and its application (by machine translation)
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The invention provides a method for catalytic synthesis of [...] reagent method and its application, the [...] reagent of formula (1) as shown in the structure of the organic solution: Its catalytic synthesis method is: under protection of inert gas, (II) shown [...] catalyst copper complex and active zinc powder added to the organic solvent, under a certain temperature [...] methyl bromide, then temperature reaction until the zinc powder the reaction is complete, the obtained white suspension is [...] reagent. (II), the invention compared with the prior art, the major advantage of: provides a [...] reagent catalytic synthesis method, is formed from a copper compound as a catalyst in the synthesis of the reagent [...] effect, and in the carbonyl of methylene compounds have been obtained in the application. (by machine translation)
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Paragraph 0039; 0040; 0043; 0044; 0045; 0046
(2018/04/28)
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- STILBENE DERIVATIVES FOR THE TREATMENT OF CNS AND OTHER DISORDERS
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The present application discloses stilbene derivative compounds and compositions, and methods for treating ocular diseases, neurological disorders and protein aggregation-related disorders in patients using the compounds and compositions as disclosed herein.
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Paragraph 00134
(2018/12/03)
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- STILBENE AND FUSED STILBENE DERIVATIVES AS SOLAR CELL DYES
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The present application discloses stilbene derivative compounds and phenyl- benzofuran compositions, useful in the manufacture of dye-sensitized solar cells and other similar technology.
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Paragraph 0051
(2018/12/02)
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- Irradiation-Induced Palladium-Catalyzed Decarboxylative Heck Reaction of Aliphatic N-(Acyloxy)phthalimides at Room Temperature
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It is reported that Pd(PPh3)2Cl2 in combination with 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos) under irradiation of blue LEDs efficiently catalyzes a decarboxylative Heck reaction of vinyl arenes and vinyl heteroarenes with aliphatic N-(acyloxy)phthalimides at room temperature. A broad scope of secondary, tertiary, and quaternary carboxylates, including α-amino acid derived esters, can be applied as amenable substrates with high stereoselectivity. The experimental observation was explained by excitation-state reactivity of the palladium complex under irradiation to induce single-electron transfer to activate N-(acyloxy)phthalimides, and to suppress undesired β-hydride elimination of alkyl palladium intermediates.
- Wang, Guang-Zu,Shang, Rui,Fu, Yao
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supporting information
p. 888 - 891
(2018/02/10)
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- Coumarin green light dyestuff containing triphenylamine ethylene side chain
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The invention relates to a coumarin green light dyestuff containing a triphenylamine ethylene side chain. The green light dyestuff has a structure shown as a formula (I), wherein R1, R2, and R3 are independently represented as hydrogen, C1 to C8 substituted or unsubstituted alkyl, alkoxyl or halogen. A photo-physical property test on the coumarin green light dyestuff shows that a molecule shown as the formula (I) has high fluorescent quantum yield and has very good application potential in the aspect of a green-light light conversion film material. The material has high light emitting property, is not sensitive to a preparation process and has a relatively stable emission spectrum in relatively large doping concentration and temperature ranges. (The formula (I) is shown as the description.).
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Paragraph 0045; 0046; 0047; 0048
(2017/07/22)
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- Irradiation-Induced Heck Reaction of Unactivated Alkyl Halides at Room Temperature
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The palladium-catalyzed Mizoroki-Heck reaction is arguably one of the most significant carbon-carbon bond-construction reactions to be discovered in the last 50 years, with a tremendous number of applications in the production of chemicals. This Nobel-Prize-winning transformation has yet to overcome the obstacle of its general application in a range of alkyl electrophiles, especially tertiary alkyl halides that possess eliminable β-hydrogen atoms. Whereas most palladium-catalyzed cross-coupling reactions utilize the ground-state reactivity of palladium complexes under thermal conditions and generally apply a single ligand system, we report that the palladium-catalyzed Heck reaction proceeds smoothly at room temperature with a variety of tertiary, secondary, and primary alkyl bromides upon irradiation with blue light-emitting diodes in the presence of a dual phosphine ligand system. We rationalize that this unprecedented transformation is achieved by utilizing the photoexcited-state reactivity of the palladium complex to enhance oxidative addition and suppress undesired β-hydride elimination.
- Wang, Guang-Zu,Shang, Rui,Cheng, Wan-Min,Fu, Yao
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supporting information
p. 18307 - 18312
(2017/12/27)
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- Direct Olefination of Fluorinated Quinoxalines via Cross- Dehydrogenative Coupling Reactions: A New Near-Infrared Probe for Mitochondria
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A large library of 5,8-distyrylquinoxaline fluorophores was synthesized in good-to-excellent yields via a palladium-catalyzed oxidative C–H/C–H cross-coupling of electron-deficient fluorinated quinoxalines with electron-rich styrenes. The resulting quinoxaline fluorophores (Qu-Fluors) exhibited tunable color emissions with the quantum yields of up to 83% and large Stokes shifts of up to 6236 cm?1 in dichloromethane. The bioimaging performance of the Qu-Fluors was shown to have potential as near-infrared fluorescent probes for mitochondria. (Figure presented.).
- Zhang, Zeyuan,Zheng, Yiwen,Sun, Zuobang,Dai, Zhen,Tang, Ziqiang,Ma, Jiangshan,Ma, Chen
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supporting information
p. 2259 - 2268
(2017/07/07)
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- Triephnylamine-based organic dye and its synthetic method and application
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The invention relates to an organic dye, in particular to a triphenylamine-based organic dye and a synthesizing method and application of the triphenylamine-based organic dye. An electron supplying part is a triphenylamine group, and an electron absorption part is a cyano crylic acid group. Compared with the prior art, the carboxyl (-COOH) in dye molecules is an optimally chosen absorption functional group which can ensure that the dye molecules are chemically absorbed to amphoteric TiO2 surfaces, so that electron cloud overlapping happens on an LUMO (lowest unoccupied molecular orbital) of the dye molecules and a 3d (three-dimensional) orbital of TiO2; and meanwhile, the triphenylamine group and derivatives of the triphenylamine group have strong electron supplying capability; three benzene rings have a non-coplanar structure and can prevent molecules from overlapping and reduce the aggregation of the dye; and the D-pi-A structure of the dye molecule has a larger conjugated system, so that the absorption spectrum of the dye is subjected to red shift and broadening, light capture capability of the dye molecules is effectively enhanced, and utilization rate of visible light is increased.
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Paragraph 0009; 0010; 0013; 0014
(2016/10/07)
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- Position effect based on anthracene core for OLED emitters
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Green-orange emitters based on anthracene core have been successfully synthesized by substitution with triphenylamine side group in the 9,10 or 2,6 positions. There are larger blue shifts in the UV-visible absorption and PL spectra of the synthesized 2,6-substituted derivative compared to the 9,10-substituted derivative. When the synthesized compounds were used as emitting layers in non-doped OLED devices, a related trend was observed in their optical properties. In particular, the OLED device containing the 2,6-substituted derivative was found to exhibit excellent characteristics, with maximum EL emission at 518 nm, pure green emission with CIE coordinates of (0.334, 0.604), and external quantum efficiency of 2.83%.
- Kang, Hyeonmi,Shin, Hwangyu,Kim, Beomjin,Park, Jongwook
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p. 3045 - 3048
(2016/03/19)
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- ORGANIC COMPOUND AND ORGANIC OPTOELECTRIC DEVICE INCLUDING THE SAME
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The present invention relates to an organic compound represented by the following chemical formula 1 or 2, and an organic optoelectronic device containing the organic compound. In the chemical formula 1 and 2, Ar1, L1, L2, R1, and R2 are the same as described in a specification.COPYRIGHT KIPO 2016
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Paragraph 0224-0228
(2016/10/10)
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- ORGANIC COMPOUND AND ORGANIC OPTOELECTRIC DEVICE INCLUDING THE SAME
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The present invention relates to an organic compound represented by chemical formula 1 or 2, and an organic optoelectric device including the same. Ar^1, L^1, L^2, R^1, and R^2 are the same as described in the specification.COPYRIGHT KIPO 2015
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Paragraph 0226-0228
(2016/10/10)
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- Pd-indenyl-diphosphine: An effective catalyst for the preparation of triarylamines
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A new Buchwald-type diphosphine ligand has been developed for applications in Pd-catalyzed amination reactions towards the preparation of triarylamines. The catalyst can be used to perform the amination of a diverse array of aryl and heteroaryl chlorides.
- Yan, Meng-Qi,Yuan, Jia,Pi, Yun-Xiao,Liang, Jin-Hua,Liu, Yan,Wu, Qing-Guo,Luo, Xue,Liu, Sheng-Hua,Chen, Jian,Zhu, Xiao-Lei,Yu, Guang-Ao
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supporting information
p. 451 - 454
(2016/01/12)
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- Aggregation-enhanced emission in fluorophores containing pyridine and triphenylamine terminals: Restricted molecular rotation and hydrogen-bond interaction
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Restriction on molecular rotation of fluorophores reduces non-radiative decay channels and promotes strong fluorescence due to aggregation-enhanced emission (AEE) behavior. To evaluate the important role of restricted molecular rotation on AEE behavior, tetraphenylthiophene (TP) derivatives with two pyridine (Py) or two triphenylamine (TPA) terminals were synthesized and characterized to be AEE-active fluorophores. Because of the efficient hindered molecular rotation of the larger TPA terminals, TP-2TPA emitted with higher emission efficiency than TP-2Py with smaller Py terminals. In addition, Py and TPA terminals can serve as hydrogen-bond (H-bond) accepting groups to bind with H-bond donating hydroxyl groups in poly(vinyl phenol) (PVPh) and poly(vinyl alcohol) (PVA) to further reinforce rotational restriction on the TP-2Py and TP-2PTA fluorophores. TP-2Py and TP-2PTA were therefore blended with PVPh and PVA and the emissive properties of the resultant blends were characterized and compared with the unblended TP-2Py and TP-2PTA to emphasize the role of H-bond on restricted molecular rotation.
- Deng, Shiang-Lin,Chen, Tai-Lin,Chien, Wei-Lun,Hong, Jin-Long
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p. 651 - 659
(2014/01/06)
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- Enhancing the coplanarity of the donor moiety in a donor-acceptor molecule to improve the efficiency of switching phenomenon for flash memory devices
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Two conjugated small molecules were synthesized by Heck coupling reaction, wherein 1,8-naphthalimide acted as an electron acceptor, while either carbazole or triphenylamine, which contributed the different coplanarity, acted as electron donors, respectively. The devices based on both materials show non-volatile flash memory characteristics, and the effect of molecular coplanarity of the donor groups on the device performance was precisely studied. The results indicated that the reproducibility of the switching phenomenon for the memory device based on the carbazole containing naphthalimide derivative was much better than that based on the triphenylamino based naphthalimide due to the rigid carbazole moiety which improved the surface morphology as revealed by atomic force microscopy measurement. Therefore, the significance of the coplanarity of the donor moiety on improving reproducibility of switching phenomenon for memory device applications was revealed.
- Ren, Wusheng,Zhuang, Hao,Bao, Qing,Miao, Shifeng,Li, Hua,Lu, Jianmei,Wang, Lihua
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p. 127 - 134
(2013/11/06)
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- Two-photon lithography in visible and NIR ranges using multibranched-based sensitizers for efficient acid generation
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We investigated methodically the one- and two-photon absorption properties of a series of multibranched triphenylamine-based chromophores incorporating 4-(methylthio)styryl fragments as external substituents. Some relevant structure-property relationships relative to these highly fluorescent compounds have been derived based on emission anisotropy measurements, quantum chemical calculations and the use of the exciton coupling theory. Even though branching effects lead to a cooperative enhancement of the two-photon absorption (2PA), all compounds exhibit relatively low-to-moderate 2PA cross-sections (δ ≤ 100 GM) in the NIR region. However, the 'so-called' one-photon resonance enhancement effect leads to a remarkable increase of δ by more than one order of magnitude in the visible range. This strong 2PA ability has been associated with an efficient photosensitization of iodonium salt to elaborate a new bicomponent photoacid generator, which is readily two-photon activable at 532 nm. In the visible range, the strong enhancement of the efficiency of the two-photon induced polymerization is clearly demonstrated as compared with that observed in the NIR region. This journal is the Partner Organisations 2014.
- Jin, Ming,Xie, Jianchao,Malval, Jean-Pierre,Spangenberg, Arnaud,Soppera, Olivier,Versace, Davy-Louis,Leclerc, Tiffanie,Pan, Haiyan,Wan, Decheng,Pu, Hongting,Baldeck, Patrice,Poizat, Olivier,Knopf, Stephan
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p. 7201 - 7215
(2014/12/10)
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- Heterocyclic Compound and Organic Light-Emitting Diode including the same
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The present invention refers to a heterocyclic compound as represented by Formula 1. The heterocyclic compound may be used in an organic layer of an organic light-emitting diode. An organic light-emitting diode includes a first electrode, a second electrode and an organic layer, and the organic layer includes the heterocyclic compound represented by Formula 1. The organic light-emitting diode may be used in a flat panel display device, in which the first electrode of the organic light-emitting diode may be electrically connected to a source or drain electrode of a thin film transistor.
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Paragraph 0137
(2014/09/03)
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- Rationalization of dye uptake on titania slides for dye-sensitized solar cells by a combined chemometric and structural approach
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A model photosensitizer (D5) for application in dye-sensitized solar cells has been studied by a combination of XRD, theoretical calculations, and spectroscopic/chemometric methods. The conformational stability and flexibility of D5 and molecular interactions between adjacent molecules were characterized to obtain the driving forces that govern D5 uptake and grafting and to infer the most likely arrangement of the molecules on the surface of TiO2. A spectroscopic/chemometric approach was then used to yield information about the correlations between three variables that govern the uptake itself: D5 concentration, dispersant (chenodeoxycholic acid; CDCA) concentration, and contact time. The obtained regression model shows that large uptakes can be obtained at high D5 concentrations in the presence of CDCA with a long contact time, or in absence of CDCA if the contact time is short, which suggests how dye uptake and photovoltaic device preparation can be optimized.
- Gianotti, Valentina,Favaro, Giada,Bonandini, Luca,Palin, Luca,Croce, Gianluca,Boccaleri, Enrico,Artuso, Emma,Van Beek, Wouter,Barolo, Claudia,Milanesio, Marco
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p. 3039 - 3052
(2015/09/28)
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- Synthesis, characterization and properties of novel star-shaped π-conjugated oligomers with triphenylamine core
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Four new star-shaped π-conjugated oligomers (TPA-CZ3, TPA-TPA3, TPA-PTZ3 and TPA-BT3) with triphenylamine as a core and different electron-donating ability groups, carbazole, triphenylamine, phenothiazine and bithiophene, as peripheral units have been designed and synthesized via the Heck reaction. These oligomers show good solubility in common organic solvents. Their photophysical, electrochemical, electronic structure and charge transfer properties between these star-shaped π-conjugated oligomers and N,N′-bis(1-ethylpropyl)-3, 4:9,10-perylene bis(tetracarboxyl diimide) (EP-PDI) have been investigated by UV-vis absorption spectra, photoluminescence (PL) spectra, cyclic voltammetry (CV) measurement, theoretical calculations and fluorescence quenching. The results show that the absorptions and fluorescences of TPA-CZ3, TPA-TPA3 and TPA-PTZ3 are red shifted with the electron-donating ability of the peripheral unit increasing from carbazole to triphenylamine and phenothiazine. In addition, although the bithiophene group has a weaker electron-donating ability than carbazole, triphenylamine and phenothiazine, the absorption and fluorescence of TPA-BT3 have a red shift than those of TPA-CZ3, TPA-TPA3 and TPA-PTZ3 because TPA-BT3 has a longer conjugation length than TPA-CZ3, TPA-TPA3 and TPA-PTZ3. The triphenylamine core and the peripheral units can constitute a large conjugated structure. The fluorescence quenching properties indicate that efficient charge transfer can happen between the star-shaped oligomers and EP-PDI. The core of these new star-shaped oligomers is electron-donating group, triphenylamine. The peripheral units are four hole-transporting chromophores with different electron-donating ability. The photophysical properties of these oligomers can be tuned through changing the electron-donating ability and conjugation length of the peripheral units.
- Liu, Leijing,Guo, Qing,Li, Jiyang,Yao, Bin,Tian, Wenjing
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p. 456 - 464
(2013/08/25)
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- Synthesis and properties of new luminescent hole transporting materials containing triphenylamine and carbazole units
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Two new blue luminescent hole transporting materials (HTM) containing triphenylamine, carbazole units and olefinic linkers (TM1 and TM2) were synthesized via Wittig reaction and characterized by 1H NMR, FT-IR, and HRMS. The compounds show good solubility in common organic solvents such as dichloromethane, chloroform, tetrahydrofuran and dimethyl formamide. Their optical, electrochemical and crystalline properties were investigated by using UV-Vis, photoluminescence (PL) spectra, cyclic voltammetry (CV) and differential scanning calorimetry (DSC), respectively. Quantum-chemical calculation was performed to obtain their optimized structures and the electron distribution of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) energy levels. The UV-Vis absorption and PL spectra of the two compounds in solid state were found to be similar to that when they were in dilute THF, which suggests that these compounds remain as an amorphous state in solid films. CV measurements show that the two compounds embody suitable HOMO levels (in a range of -5.28 to -5.23 eV) for hole injection, which is consistent with the calculation consequence. Two compounds possess high glass-transition temperature (Tg) at 96.61 and 90.74 °C for TM1 and TM2, respectively, suggesting the two compounds could form stable amorphous glassy states. The experimental results show that the synthesized compounds have great potential for application in organic light-emitting devices (OLEDs).
- Gao, Wenzheng,Wang, Shirong,Xiao, Yin,Li, Xianggao
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p. 215 - 221,7
(2012/12/12)
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- Synthesis, photophysical and iron-sensing properties of terpyridyl-based triphenylamine derivatives
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A series of new terpyridyl phenyl/styryl triphenylamine chromophores were designed and synthesized. The branching number and the rigid/flexible bridge structures had a remarkable effect on the photophysical, selectivity and sensitivity for Fe(II) ion properties of these chromophores. The fluorescence lifetimes of the rigid terpyridyl phenyl triphenylamine chromophores are longer than that of the flexible terpyridyl styryl triphenylamine derivatives. The terpyridyl phenyl/styryl triphenylamine chromophores present an increasing fluorescence lifetime with the increase in the number of branches from 1 to 3. The terpyridyl flexible styryl triphenylamine derivatives have a higher sensitivity than that of the terpyridyl rigid phenyl triphenylamine derivatives for Fe(II) ion in neutral aqueous solution amongst other divalent metal ions such as Cu2+, Co2+, Ni2+, Hg2+, Mg2+, Pb2+, Zn2+.
- Fan, Congbin,Wang, Xiaomei,Ding, Ping,Wang, Jingjing,Liang, Zuoqin,Tao, Xutang
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p. 757 - 767
(2012/11/07)
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- Synthesis of π-conjugated two generation dendrimer composed of p-phenylenevinylene dendron and triphenylamine surface group
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π-Conjugated two generation dendrimer composed of p-phenylenevinylene dendron and triphenylamine surface group was synthesized via a convergent route. The dendrimer shows high solubility in organic solvents and fluorescence emission resulting from the p-phenylenevinylene site.
- Mizusaki, Masanobu,Yamada, Yuichiro,Obara, Satoru,Tada, Kentaro
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body text
p. 516 - 517
(2012/07/14)
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- Synthesis and photophysical properties of two-photon absorbing spirofluorene derivatives
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New spirofluorene-based quadrupolar two-photon absorbing dyes having triphenylamine and N,Ndibutylaniline as electron donors at the end of molcules were designed and synthesized. The thirdorder nonlinear optical properties of these compounds were studied using a two-photon excited fluorescence method. They were found to have high two-photon absorption cross-section owing to extended conjugation of the spirofluorene moiety. The effect of varying the donor strength could be discerned by comparing the two compounds. They were successfully used as a photosensitizers for two-photon initiated polymerization of three-dimensional micro-objects. Copyright
- Lim, Jea-Geon,Prabhakaran, Prem,Park, Jin Sun,Son, Yong,Kim, Tae-Dong,Yang, Dong-Yol,Lee, Kwang-Sup
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experimental part
p. 4403 - 4408
(2012/08/28)
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- Triphenylamine-containing D-A-D molecules with (dicyanomethylene)pyran as an acceptor unit for bulk-heterojunction organic solar cells
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Two new triphenylamine (TPA)-containing D-A-D molecules with TPA as the donor unit (D), (dicyanomethylene)pyran (PM) as the acceptor unit (A) and thienylenevinylene (TV) or 4-hexyl-thienylenevinylene (HTV) as the conjugated pi-bridge, TPA-TV-PM and TPA-HTV-PM, have been designed and synthesized for solution-processable organic solar cells (OSCs). The optical and electrochemical properties of these linear molecules were studied. The compounds exhibit broad absorption in the visible region with lower HOMO energy levels, which are desirable for application as a donor in organic solar cells. The OSC devices were fabricated by spin-coating the blend solution of the molecules as the donor and PC70BM as the acceptor (1:3, w/w). The power conversion efficiency of the OSCs based on TPA-TV-PM and TPA-HTV-PM reached 2.06% and 2.10%, respectively, under the illumination of AM.1.5, 100 mW cm-2. The Royal Society of Chemistry 2011.
- Zhang, Jing,Wu, Guanglong,He, Chang,Deng, Dan,Li, Yongfang
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p. 3768 - 3774
(2013/01/10)
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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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- Fluorenylvinylenes bridged triphenylamine-based dyes with enhanced performance in dye-sensitized solar cells
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We have synthesized a series of new dipolar organic dyes Bn (n=0, 1, 2) employing triarylamine as the electron-donor, 2-cyanoacrylic acid as the electron-acceptor, and fluorenevinylene as the conjugated bridge, which were used as sensitizers in dye-sensitized solar cells. It is found that the solar-energy-to-electricity conversion efficiencies of the prepared DSSCs are in the range of 2.79-5.56%, which reach 35-70% of a standard device based on N719 fabricated and measured under the same conditions. The DSSC sensitized with B1 with balanced length of conjugated bridge shows the highest photo-to-electrical energy conversion efficiency and the open-circuit photovoltage (Voc) of 0.86 V.
- Zhou, Huipeng,Xue, Pengchong,Zhang, Yuan,Zhao, Xin,Jia, Junhui,Zhang, Xiaofei,Liu, Xingliang,Lu, Ran
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experimental part
p. 8477 - 8483
(2011/11/29)
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- Geometrical effect of stilbene on the performance of organic dye-sensitized solar cells
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New metal-free organic donor-bridge-acceptor dyes comprising a triphenylamine moiety as the electron donor (D), a cyanoacrylic acid moiety as the electron acceptor (A), and a conjugated chromophore between D and A as a spacer (S) were synthesized for the application of dye-sensitized solar cells (DSSCs). Two types of S were designed, one contains a normal stilbene backbone (dye 1) and the other contains a 2-phenylindene moiety (dye 2) with the central double bond locked in a transoid geometry. The performance of DSSCs made with these two types of dyes was compared, and it was found that the inhibition of trans/cis isomerization of the central double bond was advantageous to the efficiency of DSSCs. The phenomenon was investigated by a comparison of their photophysical properties, and rationalized by quantum mechanical calculations by using density functional theory (DFT) at the B3LYP/6-31G(d,p) level. The electronic transitions were analyzed by time-dependent DFT, and the results were consistent with the experimental observations. The DSSCs were fabricated using both types of materials, and the performance was recorded under AM 1.5G irradiation (100 mW cm-2) condition. The overall conversion efficiencies of dye 2 (5.14-5.67%) were higher than those of dye 1 (4.52-4.98%). Both the short-circuit photocurrent density (Jsc) and the open-circuit voltage (Voc) were improved in 2 with respect to those of 1. The Royal Society of Chemistry.
- Lin, Yan-Duo,Chow, Tahsin J.
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scheme or table
p. 14907 - 14916
(2012/02/04)
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- The photophysical properties and two-photon absorption of novel triphenylamine-based dendrimers
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Novel triphenylamine-based dendrimers were synthesized and characterized by FT-IR, elemental analysis, 1H NMR spectroscopy, and MALDI-TOF mass spectrometry. The linear photophysical properties including absorption, one-photon induced fluorescence and the fluorescence lifetimes in different solvents were investigated. The two-photon induced fluorescence behavior was recorded in toluene solution, employing a Ti:sapphire femtosecond laser pulse. The dendrimers both emit strong blue-green fluorescence under irradiation. Two-photon excited state fluorescence cross-sections were also obtained. The two dendrimers displayed a large two-photon absorption. The polytriphenylamine dendrimer shows larger two-photon excited state fluorescence cross-sections in toluene relative to the tristriphenylamine analog, indicating that there is cooperative enhancement originating from inter-branch coupling and an increase of light-harvesting ability with increasing dendrimer size.
- Yan, Zi-Qi,Xu, Bin,Dong, Yu-Jie,Tian, Wen-Jing,Li, Ai-Wu
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scheme or table
p. 269 - 274
(2011/12/21)
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- High performance organic photosensitizers for dye-sensitized solar cells
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We report highly efficient organic photosensitizers containing π-conjugated alkoxy-substituted oligophenylenevinylene linkers with electron donor-acceptor units for dye-sensitized solar cells. TA-DM-CA showed an overall solar-to-energy conversion efficiency of 9.67% at AM 1.5 illumination (100 mW cm-2).
- Im, Hunbae,Kim, Sukwon,Park, Chanmoo,Jang, Seok-Hoon,Kim, Chang-Ju,Kim, Kyungkon,Park, Nam-Gyu,Kim, Chulhee
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supporting information; scheme or table
p. 1335 - 1337
(2010/07/05)
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- Switching high two-photon efficiency: From 3,8,13-substituted triindole derivatives to their 2,7,12-isomers
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Bridging the triindole core and triarylboryl acceptor by an ethenylene linker at the 3,8,13- or 2,7,12-position, the resultant 3-BET and 2-BET show two-photon absorption (TPA) cross sections of δ = 2100 and 2500 GM (at 810 nm by femtosecond pulses in THF), respectively. The TPA enhancement of the 2,7,12-isomers is also found when comparing 3-BYT and 2-BYT (δ = 870 and 1900 GM) and 3-NET and 2-NET (36 and 400 GM).
- Ji, Lei,Fang, Qi,Yuan, Mao-Sen,Liu, Zhi-Qiang,Shen, Yu-Xiang,Chen, Hong-Feng
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supporting information; experimental part
p. 5192 - 5195
(2011/02/27)
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- Synthesis and photovoltaic properties of novel solution-processable triphenylamine-based dendrimers with sulfonyldibenzene cores
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Three conjugated dendrimers containing electron-accepting sulfonyldibenzene (SDB) cores and electron-donating triphenylamine dendrons have been synthesized through a convergent synthetic strategy without any protection/deprotection chemistry. The dendrimers were highly soluble in common organic solvents, and could form good quality optical films by spin coating. Their thermal, optical and electrical properties are manipulated by attaching different peripheral dendrons. Using these dendrimers as donors and [6,6]-phenyl C61-butyric acid methyl ester (PCBM) as acceptor, the bulk heterojunction solar cells with a structure of ITO-PEDOT-dendrimers:PCBM-LiF-Al were fabricated. The cell based on dendrimer G0 shows a relatively high power-conversion efficiency (PCE) of 0.34% under AM 1.5 illumination of 100 mW cm-2.
- Li, Kunpeng,Qu, Jiali,Xu, Bin,Zhou, Yinhua,Liu, Leijing,Peng, Ping,Tian, Wenjing
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experimental part
p. 2120 - 2127
(2009/12/25)
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- Electronic and vibronic contributions to two-photon absorption in donor-acceptor-donor squaraine chromophores
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Many squaraines have been observed to exhibit two-photon absorption at transition energies close to those of the lowest energy one-photon electronic transitions. Here, the electronic and vibronic contributions to these low-energy two-photon absorptions ar
- Ohira, Shino,Rudra, Indranil,Schmidt, Karin,Barlow, Stephen,Chung, Sung-Jae,Zhang, Qing,Matichak, Jon,Marder, Seth R.,Bredas, Jean-Luc
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supporting information; experimental part
p. 11082 - 11091
(2009/11/30)
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- A facile convergent procedure for the preparation of triphenylamine-based dendrimers with truxene cores
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A simple convergent procedure has been developed for the preparation of triphenylamine dendrons containing an alkene at the center, which can be coupled in a single step to give dendrimers that contain truxene for the core without any protection-deprotection chemistry. These conjugated dendrimers exhibit similar absorption and emission behaviors in solutions and in thin films, which are indicative of the high isolation effect of well-organized three-dimensional dendrimers. They also have high fluorescence quantum yields and high glass transition temperatures, which indicate that these dendrimers are candidates for the application in OLED as light emitting materials.
- Xia, Haijian,He, Jiating,Xu, Bin,Wen, Shanpeng,Li, Yaowen,Tian, Wenjing
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p. 5736 - 5742
(2008/09/21)
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- A highly efficient organic sensitizer for dye-sensitized solar cells
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We have synthesized a highly efficient organic dye for a dye-sensitized solar cell; the overall solar-to-energy conversion efficiency was 9.1% at AM 1.5 illumination (100 mW cm-2): short-circuit current density (J sc) = 18.1 mA cm-2, open circuit photovoltage (V oc) = 743 mV and fill factor (ff) = 0.675. The Royal Society of Chemistry.
- Hwang, Suyoung,Lee, Jung Ho,Park, Chanmoo,Lee, Hoinglae,Kim, Chaekyu,Park, Chiyoung,Lee, Mi-Hyeon,Lee, Wanin,Park, Jihee,Kim, Kyungkon,Park, Nam-Gyu,Kim, Chulhee
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p. 4887 - 4889
(2008/09/18)
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- The synthesis of robust, polymeric hole-transport materials from oligoarylamine substituted styrenes
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Novel styrene-based oligoarylamine monomers are described which are suitable for the preparation of polymeric hole-transport materials, with very high glass transition temperatures. The monomers are prepared using the Wittig reaction from the appropriate aldehyde precursor, which was assembled using the classical Ullmann reaction. A number of the monomers yielded high-quality crystals which facilitated X-ray characterisation. Polymerisation was achieved either by solution free-radical initiation or by condensed phase thermal autopolymerisation. The latter suggests a method of initiator-free polymerisation which may have potential for multilayer device fabrication. The Royal Society of Chemistry.
- McKeown, Neil B.,Badriya, Samer,Helliwell, Madeleine,Shkunov, Maxim
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p. 2088 - 2094
(2008/02/07)
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- One pot sequential reactions and novel products produced thereby
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A method for producing sequenced reaction products comprising performing, in one pot, a first reaction at a lower temperature followed by a second reaction at a higher temperature in the presence of a catalyst system comprising a proazahosphatrane in combination with a palladium compound is provided. In one embodiment, the first reaction is a double amination reaction and the second reaction is an arylation. Use of one pot and a single catalyst system for each set of sequential reactions is efficient and economical. Novel N,N-diarylaminostyrenes and N,N-diarylaminostilbenes are produced according to the methods described herein.
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Page/Page column 9-10
(2010/11/24)
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- CHARGE TRANSPORT MATERIALS
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Charge transport materials are provided, and methods for making the same.
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Page/Page column 19-20
(2008/06/13)
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