- Fluorophore-functionalized graphene oxide with application in cell imaging
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In this work, we fabricated a novel triphenylamine-derivative (DNDT)-modified nanographene oxide by following a simple gram-scale method. The product showed interesting optical properties and good potential for use in bioimaging applications. This fluorescent carbon material could be readily internalized by HepG2 cells and was clearly visualized to accumulate mainly in the nucleus.
- Lei, Lei,Ma, Hengchang,Yang, Manyi,Qin, Yanfang,Ma, Yucheng,Wang, Tao,Yang, Yuan,Lei, Ziqiang,Lu, Dedai,Guan, Xiaolin
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- Facile synthesis of triphenylamine and phenothiazine-based Schiff bases for aggregation-induced enhanced emission, white light generation, and highly selective and sensitive copper(ii) sensing
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Two new Schiff bases, one triphenylamine-based (TPA-SB) and another phenothiazine-based (PTz-SB), were synthesized via facile reactions. Both molecules showed aggregation-induced enhanced emission (AIEE) properties. In fact, an 8-fold increase in the fluo
- Anand, Vivek,Sadhasivam, Balaji,Dhamodharan, Raghavachari
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- Novel D-π-A type triphenylamine based chromogens for DSSC: Design, synthesis and performance studies
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In this work, four novel D-π-A organic dyes (MH, MT, DT, DH) consisting of triphenylamine as an electron donor and 2,4-thiazolidinedione/hydantoin as anchoring groups were designed and synthesized for use in dye-sensitized solar cells (DSSCs). The synthesized dyes were characterized using FT-IR, NMR, mass spectrometry, absorbance and electrochemical measurements. The photophysical, electrochemical and photovoltaic properties of the solar cells based on these dyes were investigated to study the effect of two different anchoring groups on the performance of the dye-sensitized solar cells. The dye consisting of two hydantoin anchoring groups shows the highest conversion efficiency of 2.70% (short-circuit current = 7.60 mA cm-2, open circuit voltage = 570 mV, and fill factor = 0.62 under standard AM1.5G irradiation) compared to the other designed dyes. The observed results will provide basic information for the future design of sensitizers with different anchoring groups for photovoltaic applications.
- Hosseinzadeh, Behzad,Beni, Alireza Salimi,Azari, Masoumeh,Zarandi, Maryam,Karami, Marzeih
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- A novel triphenylamine-based dye sensitizer supported on titania nanoparticles and the effect of titania fabrication on its optical properties
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A new synthesised triphenylamine-based dye having a branched structure with one OH-ending branch able to interact with the surface hydroxyl moieties of mesoporous TiO2 is reported. Optical properties of the dye-titania hybrid material are presented and the higher efficiency of the dye on pure anatase TiO2 compared to the commercial Degussa P25, which contains a rutile phase component, is confirmed. The optical and chemical properties of the dye make it a promising candidate as a metal-free dye for DSSCs or as a host for a variety of transition or main group metal ions for different applications.
- Moretti, Elisa,Aversa, Manuela,Scrivanti, Alberto,Storaro, Loretta,Talon, Aldo,Marin, Riccardo,Cecilia, Juan Antonio,Rodríguez-Castellón, Enrique,Polizzi, Stefano
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- Triarylamine-Pyridine-Carbonitriles for Organic Light-Emitting Devices with EQE Nearly 40%
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Highly efficient thermally activated delayed fluorescence (TADF) molecules are in urgent demand for solid-state lighting and full-color displays. Here, the design and synthesis of three triarylamine-pyridine-carbonitrile-based TADF compounds, TPAPPC, TPAmPPC, and tTPAmPPC, are shown. They exhibit excellent photoluminescence quantum yields of 79?100% with small ΔEST values, fast reverse intersystem crossing (RISC), and high horizontal dipole ratios (Θ//?= 86?88%) in the thin films leading to the enhancement of device light outcoupling. Consequently, a green organic light-emitting diode (OLED) based on TPAmPPC shows a high average external quantum efficiency of 38.8?± 0.6%, a current efficiency of 130.1?± 2.1?cd A–1, and a power efficiency of 136.3?± 2.2?lm W–1. The highest device efficiency of 39.8% appears to be record-breaking among TADF-based OLEDs to date. In addition, the TPAmPPC-based device shows superior operation lifetime and high-temperature resistance. It is worth noting that the TPA-PPC-based materials have excellent optical properties and the potential for making them strong candidates for TADF practical application.
- Chen, Yi-Kuan,Jayakumar, Jayachandran,Hsieh, Chia-Min,Wu, Tien-Lin,Liao, Chun-Cheng,Pandidurai, Jayabalan,Ko, Chang-Lun,Hung, Wen-Yi,Cheng, Chien-Hong
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- Detection of nitroaromatics based on aggregation induced emission of barbituric acid derivatives
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Barbituric acid derivatives with typical aggregation induced emission (AIE) are reported. Their emission wavelengths varied with water fraction of their solution. UV–visible absorption spectroscopy and theoretical calculations revealed the intramolecular
- Zhang, Han-Jun,Tian, Yan,Tao, Fu-rong,Yu, William,You, Kai-Yue,Zhou, Lin-Rui,Su, Xi,Li, Tian-duo,Cui, Yue-Zhi
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- Real-Time Fluorescence in Situ Visualization of Latent Fingerprints Exceeding Level 3 Details Based on Aggregation-Induced Emission
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A water-soluble probe, TPA-1OH, with aggregation-induced emission activity is synthesized and used for expedient real-time fluorescence in situ visualization of latent fingerprints (LFPs). A TPA-1OH aqueous solution exhibits nonfluorescence in pure water
- Wang, Ya-Long,Li, Chong,Qu, Hong-Qing,Fan, Cheng,Zhao, Peng-Ju,Tian, Rui,Zhu, Ming-Qiang
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- Synthesis and characterization of a new pillar[5]arene-based [1]rotaxane
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In this study, we reported the synthesis of three kinds of mono-functional pillar[5]arene derivatives PRI, PRII and R and their structures were studied by 1D and 2D NMR spectra and mass spectra. The 2D NMR spectra including 1H-13C HSQC, 1H-1H COSY and NOESY spectra indicated that PRI and PRII are both stable self-included pseudo[1]rotaxanes in CDCl3. These original structures are promising compounds for the design of pillar[5]-based [1]rotaxane. And the results showed that R could exist stable in CDCl3 and DMSO because of the coordination of N-H?O hydrogen bonding interaction and C-H?π interaction.
- Tian, Huasheng,Wang, Chunyu,Lin, Po-Han,Meguellati, Kamel
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- Axial anchoring designed silicon-porphyrin sensitizers for efficient dye-sensitized solar cells
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Using silicon as a central atom of porphyrin allows the introduction of axial ligands, which are not only employed to prevent the aggregation of the macrocycles but also anchor the dyes onto the TiO2 surface. A dye-sensitized solar cell with th
- Liu, Jing,Yang, Xichuan,Sun, Licheng
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- Axial-symmetric conjugated group promoting intramolecular charge transfer performances of triphenylamine sensitizers for dye-sensitized solar cells
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The intramolecular charge transport (ICT) process directly determines the charge generation, transport, and even injection of the dye-sensitized solar cell (DSSC) sensitizer. Herein, we constructed a new series of D-π-A system by linking 4-methoxyphenyl and triphenylamine donors with an ethynyl group having an axial-symmetric conjugated system. Since the axisymmetric conjugate group overcomes the reduction of the conjugate characteristic caused by the plane distortion, the molecular ICT performance and the electronic recombination inhibition are effectively improved. As a result, the photoelectric conversion efficiency was increased from 3.43% to 6.37% by means of the extension of the π-bridge at same time. It provides a new idea for the design and development of DSSC sensitizers in the future.
- Chen, Shaorui,Pei, Juan,Pang, Zhihan,Wu, Wenjun,Yu, Xudong,Zhang, Cong
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- A triphenylamine-based benzoxazole derivative as a high-contrast piezofluorochromic material induced by protonation
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A triphenylamine-based benzoxazole derivative exhibits a low contrast piezofluorochromic behavior under external pressure, and a high-contrast fluorescence change induced by protonation can be observed. The Royal Society of Chemistry 2014.
- Xue, Pengchong,Chen, Peng,Jia, Junhui,Xu, Qiuxia,Sun, Jiabao,Yao, Boqi,Zhang, Zhenqi,Lu, Ran
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- Crystallization-induced reversible fluorescence switching of alkyl chain length dependent thermally stable supercooled organic fluorescent liquids
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Highly stable supercooled fluorescent liquids and crystallization-induced reversible fluorescence switching have been achieved via varying the alkyl chain length of the alkoxy group in the triphenylamine aldehyde, 4-(diphenylamino)-2-methoxybenzaldehyde (
- Hariharan,Moon, Dohyun,Anthony, Savarimuthu Philip
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- Novel triphenylamine-based fluorescent probe for specific detection and bioimaging of OCl?
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Hypochlorite (OCl?) plays important roles both in physiological and pathological processes, the detection of which is of great significance. Herein, a novel fluorescent probe based on the triphenylamine-type schiff base derivative (TPAD) was developed to detect OCl?. Probe TPAD exhibited specific fluorescence response toward ClO? with the fluorescence quenching rate up to 80%, and the detection limit was estimated to be 0.8 μM. The sensing mechanism study demonstrated that TPAD reacted with ClO? via an oxidation process, which was evidenced by MS and NMR characterization. Moreover, owing to the excellent sensing properties and negligible cytotoxicity, TPAD was successfully applied in the bioimaging of OCl? in living A549 cells.
- Jiang, Yuliang,Zhang, Sheng,Wang, Bingxiang,Qian, Tao,Jin, Can,Wu, Shishan,Shen, Jian
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- Novel turn-on fluorescence sensor for detection and imaging of endogenous H2S induced by sodium nitroprusside
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Currently, fluorescence analysis method has a good application in the detection and imaging of biomarkers and has become an important analytical method. Although there are many fluorescent probes for detecting hydrogen sulfide(H2S), they are mo
- Hu, Yonghong,Song, Yiyi,Wang, Li,Yang, Wenge
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- Aggregation‐induced Emission Properties of Triphenylamine Chalcone Compounds
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Two triphenylamine chalcone derivatives 1 and 2 were synthesized through the Vilsmeier-Haack reaction and Claisen-Schmidt condensation reaction. Through ultraviolet absorption spectroscopy and fluorescence emission spectroscopy experiments, it was confirmed that these two compounds exhibited good aggregation-induced emission (AIE) behavior in ethanol/water mixtures. The solvent effect test showed with the increase of the orientation polarizability of the solvent, the Stokes shift in the solvent of compound 1 and compound 2 shows a linear change trend. Through solid state fluorescence test and universal density function theory (DFT), the existence of π-π stacking interaction in the solid state of the compound has been studied, resulting in weak fluorescence emission. pH has no effect on the fluorescence intensity of the aggregate state of excited state intramolecular proton transfer (ESIPT) molecules in an acidic environment, but greatly weakens its fluorescence intensity in an alkaline environment. Cyclic voltammetry (CV) test shows that compound 1 was more prone to oxidation reaction than compound 2. The results of thermal stability test show that the thermal stability of compound 1 was better than that of compound 2, indicating that triphenylamine chalcone derivatives can improve the thermal stability of compounds by increasing the number of branches.
- Zhang, Ying-Peng,Teng, Qi,Yang, Yun-Shang,Cao, Jing-Qi,Xue, Ji-Jun
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- Di-Triphenylamine-based AIE active Schiff base for highly sensitive and selective fluorescence sensing of Cu2+ and Fe3+
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Di-Triphenylamine based Schiff base (DTPA-SB) was obtained using facile synthetic steps, and the novel compound was thoroughly characterized using various spectroscopic techniques. The Schiff base showed aggregation-induced enhanced emission (AIEE) proper
- Anand, Vivek,Barot, Yash B.,Mishra, Roli
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- BF2 group chelated AIE fluorescent probe for polarity mapping of lipid droplets in cells and in vivo
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Lipid droplets (LDs), are multi-functional organelles with the storage of neutral lipids and proteins, participating in various of physiological processes. However, abnormal of LDs in morphology and numbers always lead to multiple diseases, including canc
- Lai, Chaofeng,Zhao, Yuping,Liang, Yun,Zou, Xiang,Lin, Weiying
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supporting information
(2021/12/02)
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- Carbazole/triphenylamine-cyanobenzimidazole hybrid bipolar host materials for green phosphorescent organic light-emitting diodes
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With a view to attain balanced charge flux for higher device performance of PhOLEDs, we have used carbazole/triphenyl amine as hole transporting moiety and cyano along with benzimidazole as electron transporting core in 3-Cbz-ImdCN, 4-Cbz-ImdCN and TPA-Im
- Patil, Bhausaheb,Lade, Jatin,Chiou, Shian-Sung,Cheng, Yen-Chia,Jadhav, Yogesh,Chetti, Prabhakar,Chang, Chih-Hao,Chaskar, Atul
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- A kind of AIE type triphenylamine derivative fluorescent probe and preparation method thereof and its application in the detection of hydrazine hydrate
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The present invention relates to an AIE type triphenylamine derivative fluorescent probe, chemically named (Z)-2- (4- (((E)4-(dimethylamino)benzene)3-(4-(diphenylamine)phenyl)acrylonitrile, the molecular formula is C36H30N4/sub
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Paragraph 0043; 0049-0052
(2022/01/10)
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- A water-soluble fluorescent sensor for the quick discrimination of H2O and D2O by notable signal outputs and the real-time monitoring of food spoilage in a non-contact mode
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Due to the very similar chemical and physical properties, D2O and H2O cannot be discriminated easily by convenient and cost-effective ways. Up to now, small organic molecules with active deprotonating ability in a very weak alkaline solution are proposed
- Dong, Fenghao,Han, Bingyang,Li, Zhao,Lu, Huiming,Lv, Jiawei,Ma, Hengchang,Sun, Yuqing,Yang, Yuan,Zhang, Bo,Zhang, Shengjun
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supporting information
p. 20441 - 20446
(2021/12/02)
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- Mn (II) Complex multi-photon absorption material as well as preparation method and application thereof
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The invention discloses Mn (II) complex multi-photon absorption material and a preparation method and application thereof, relates to the technical field of fluorescent probes, and designs and synthesizes a novel structure terpyridine Mn (II) complex. The
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Paragraph 0030-0031
(2021/10/27)
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- Microwave-assisted synthesis and luminescent properties of triphenylamine substituted mono- and di- branched benzimidazole derivatives
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Abstract: In the present work, the synthesis of the target products using sodium metasulfite (Na2S2O5) and p-toluenesulfonic acid (PTSA) separately as catalysts was studied. Herein, the liquid phase microwave method was ch
- Fu, Jiaxu,Yan, Liuqing,Wang, Shuang,Song, Hongying,Gu, Qiang,Zhang, Yumin
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p. 1485 - 1496
(2020/11/05)
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- Single-Molecule White-Light-Emitting Starburst Donor-Acceptor Triphenylamine Derivatives and Their Application as Ratiometric Luminescent Molecular Thermometers
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White-light emission (WLE) from a single molecule is a highly desirable alternative to a complex mixture of complementary colour emitters, which suffers from poor stability and reproducibility for potential use in organic electronic devices and lighting a
- Ajantha, Joseph,Yuvaraj, Palani,Karuppusamy, Masiyappan,Easwaramoorthi, Shanmugam
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supporting information
p. 11319 - 11325
(2021/07/02)
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- Benzimidazole blue-light-emitting material as well as preparation method and application thereof
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The invention discloses a benzimidazole blue-light-emitting material as well as a preparation method and application thereof. The benzimidazole blue-light-emitting material is prepared from the following compounds: 9-(4-(5, 6-difluoro-1-methyl-1H-benzo [d] imidazole-2-yl) phenyl)-9H-carbazole, 4-(5, 6-difluoro-1-methyl-1H-benzo [d] imidazole-2-yl)-N, N-diphenylamine, 2-(4-(9H-carbazole-9-yl) phenyl)-1-(4-cyanophenyl)-5-cyano-1H-benzo [d] imidazole, 1-(4-cyanophenyl)-2-(4-(diphenylamino) phenyl)-5-cyano-1H-benzo [d] imidazole, or 2-(2-(9H-carbazole-9-yl) phenyl)-1-(4-cyanophenyl)-5-cyano-1H-benzo [d] imidazole. The benzimidazole blue-light-emitting material has good thermal stability and relatively high color purity and luminous efficiency, and is an excellent electroluminescent material.
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Paragraph 0125-0129
(2021/09/26)
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- Highly efficient deep-blue light-emitting material based on V-Shaped donor-acceptor triphenylamine-phenanthro[9,10-d]imidazole molecule
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Based on novel phenanthro[9,10-d]imidazole (PI) chromophore, three deep-blue luminescent donor-acceptor molecules with different molecular configurations at the triphenylamine (TPA) core were designed and synthesized, the linear TPA-1PI, the V-shaped TPA-
- Gao, Yu,Li, Weijun,Liu, Haichao,Yang, Bing,Yu, Yue,Zhang, Shitong,Zhao, Ruiyang,Zhou, Changjiang
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- Effect of push-pull ruthenium complex adsorption conformation on the performance of dye sensitized solar cells
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A new series of tris-(bipyridyl)ruthenium-like complexes based on the 4-tripheylamine-2,2':6',2''-terpyridine (TPA) push-pull ligand was prepared by incorporation of 4-carboxypyridine (cpy), 4,4'-dicarboxi-2,2'-bipyridine (dcbpy) and 4-carboxyterpyridine ligands (ctpy) ligands, in order to adsorb them on TiO2 in different anchoring conformations. The electron photoinjection and electron recombination processes of the respective dye-sensitized solar cells were greatly influenced by the molecular structure, which defined the surface concentration and surface charge on TiO2, such that the photoconversion efficiency was 10 times larger for [Ru(py)(dcbpy) (TPAtpy)] than for the [Ru(cpy)(bpy)(TPAtpy)](PF6) dye. Molecules anchoring in a more upright position and by a larger number of sites were shown to enhance the electron injection into TiO2 conduction band (CB) improving the short-circuit current (JSC), open circuit voltage (Voc) and the overall photoconversion efficiency. However, a positive net charge in the dye increased the back electron-transfer reactions and induced a decrease in both Voc and conversion efficiency.
- Araki, Koiti,Guimaraes, Robson R.,Matias, Tiago A.,Rosero, Wilmmer A. A.
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p. 2250 - 2264
(2020/10/13)
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- A class of asymmetric V-shaped organic dye sensitizers, preparation method and applications thereof
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The invention discloses a class of asymmetric V-shaped organic dye sensitizers, wherein the molecules adopt triphenylamine and phenothiazine as electron donating groups, a long carbon chain is introduced into the N atom of the phenothiazine, benzothiazole
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Paragraph 0028-0031
(2020/03/09)
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- Guest Inclusion Modulates Concentration and Persistence of Photogenerated Radicals in Assembled Triphenylamine Macrocycles
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Substituted triphenylamine (TPA) radical cations show great potential as oxidants and as spin-containing units in polymer magnets. Their properties can be further tuned by supramolecular assembly. Here, we examine how the properties of photogenerated radical cations, intrinsic to TPA macrocycles, are altered upon their self-assembly into one-dimensional columns. These macrocycles consist of two TPAs and two methylene ureas, which drive the assembly into porous organic materials. Advantageously, upon activation the crystals can undergo guest exchange in a single-crystal-to-single-crystal transformation generating a series of isoskeletal host-guest complexes whose properties can be directly compared. Photoinduced electron transfer, initiated using 365 nm light-emitting diodes, affords radicals at room temperature as observed by electron paramagnetic resonance (EPR) spectroscopy. The line shape of the EPR spectra and the quantity of radicals can be modulated by both polarity and heavy atom inclusion of the encapsulated guest. These photogenerated radicals are persistent, with half-lives between 1 and 7 d and display no degradation upon radical decay. Re-irradiation of the samples can restore the radical concentration back to a similar maximum concentration, a feature that is reproducible over several cycles. EPR simulations of a representative spectrum indicate two species, one containing two N hyperfine interactions and an additional broad signal with no resolvable hyperfine interaction. Intriguingly, TPA analogues without bromine substitution also exhibit similar quantities of photogenerated radicals, suggesting that supramolecular strategies can enable more flexibility in stable TPA radical structures. These studies will help guide the development of new photoactive materials.
- Sindt, Ammon J.,Dehaven, Baillie A.,Goodlett, Dustin W.,Hartel, Johannes O.,Ayare, Pooja J.,Du, Yong,Smith, Mark D.,Mehta, Anil K.,Brugh, Alexander M.,Forbes, Malcolm D. E.,Bowers, Clifford R.,Vannucci, Aaron K.,Shimizu, Linda S.
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supporting information
p. 502 - 511
(2020/01/03)
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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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supporting information
p. 6233 - 6236
(2020/06/22)
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- Synthesis of triphenylamine (TPA) dimers and applications in cell imaging
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A variety of triphenylamine (TPA) are shown to undergo C–C bond formation using quinone-based chloranil/H+ reagent as the metal free oxidative system to afford triphenylamine dimers very conveniently. Then, TPA dimers have been further converte
- Yuan, Yang,Yin, Pei,Wang, Tao,Yang, Zengming,Yin, Weidong,Zhang, Shaoxiong,Qi, Chunxuan,Hengchang, Ma
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- Photosensitive dye taking carbazole and triphenylamine as D-D-π-A structure of two-stage electron donor as well as preparation method and application thereof (by machine translation)
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The invention belongs to the field of solar cells and discloses a photosensitive dye taking carbazole and triphenylamine as a two-stage electron donor and D-D-π-A structure as well as a preparation method and application of the photosensitive dye as a π conjugated bridge. The preparation method is simple, the process is easy to control, the raw material source is wide, the price is low, the prepared photosensitive dye is high in purity, high in yield and suitable for industrial production. The photosensitive dye is used for preparing a photo-sensitized solar cell. (by machine translation)
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Paragraph 13; 14; 16; 17; 22; 24-28
(2020/09/01)
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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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Paragraph 0116-0118; 0122-0123
(2020/07/29)
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- DIPHENYLAMINO-METHYLENE MALONONITRILE BASED COMPOUNDS AS FLUORESCENCE PROBES
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The present invention provides compounds of formula (I) and formula (II): or a pharmaceutically acceptable salt or a stereoisomer thereof; wherein, ring A and ring B have the meanings given in the specification. The compounds of the present disclosure are useful as fluorescence probe in detecting tubulin in a sample and therefore useful for the diagnosis of tubulin and its associated diseases like cancer in a subject.
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Page/Page column 15
(2020/03/23)
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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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- DYE COMPOSITION, FLUORESCENT COMPLEX AND LIGHT CONVERSION FILM COMPRISING THE SAME
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The present invention relates to a dye composition, a fluorescent complex and a light conversion film including the same. The dye composition according to the present invention maintains a basic D-A (DONOR-ACCEPTOR) structure of a BODIPY-based dye to retain original properties thereof and additionally includes a compound having twisted intramolecular charge transfer (TICT) characteristics for introducing a three-dimensional structure, thereby additionally having properties enabling aggregation induced fluorescence emission enhancement (AIEE) and increase of generation of singlet oxygen in addition to the existing properties. Therefore, the dye composition may exhibit more excellent optical characteristics to be usefully applied to a fluorescence field such as a fluorescent complex, a light conversion film including the same, and the like.COPYRIGHT KIPO 2020
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Paragraph 0109; 0110
(2020/09/01)
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- Based on the complementary color of a pH adjustable single molecule white light material and its preparation method (by machine translation)
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Based on the complementary color of a pH adjustable single molecule white light material and its preparation method. The invention belongs to organic chemical and material chemical technology field, in particular to the use of multi-purpose organic chromo
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Paragraph 0027; 0028
(2019/03/06)
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- Triphenylamine derivative with AIE characteristic, preparation method and application thereof
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The invention discloses a triphenylamine derivative with AIE characteristics, which is prepared by reacting 4-formyl triphenylamine with 2-aminobenzimidazole in the presence of a solvent and a catalyst by stirring and refluxing the reactants at 60-80 DEG
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Paragraph 0068-0070
(2019/08/02)
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- Barbituric acid derivative as well as preparation method and application thereof
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The invention provides a barbituric acid derivative as well as a preparation method and application thereof. The chemical structural formula is shown in the specification, and R is hydrogen, methyl orphenyl. The preparation method comprises the following
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Paragraph 0056-0059
(2019/08/01)
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- Metal-Bonded Redox-Active Triarylamines and Their Interactions: Synthesis, Structure, and Redox Properties of Paddle-Wheel Copper Complexes
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Four new triphenylamine ligands with different substituents in the para position and their corresponding copper(II) complexes are reported. This study includes their structural, spectroscopic, magnetic, and electrochemical properties. The complexes possess a dinuclear copper(II) paddle-wheel core, a building unit that is also common in metal-organic frameworks. Electrochemical measurements demonstrate that the triphenylamine ligands and the corresponding complexes are susceptible to oxidation, resulting in the formation of stable radical cations. The square-wave voltammograms observed for the complexes are similar to those of the ligands, except for a slight shift in potential. Square-wave voltammetry data show that, in the complexes, these oxidations can be described as individual one-electron processes centered on the coordinated ligands. Spectroelectrochemistry reveals that, during the oxidation of the complexes, no difference can be detected for the spectra of successively oxidized species. For the absorption bands of the oxidized species of the ligands and complexes, only a slight shift is observed. ESR spectra for the chemically oxidized complexes indicate ligand-centered radicals. The copper ions of the paddle-wheel core are strongly antiferromagnetic coupled. DFT calculations for the fully oxidized complexes indicate a very weak ferromagnetic coupling between the copper ions and the ligand radicals, whereas a very weak antiferromagnetic coupling is found among the ligand radicals.
- Akintola, Oluseun,B?hme, Michael,Rudolph, Manfred,Buchholz, Axel,G?rls, Helmar,Plass, Winfried
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p. 271 - 284
(2019/01/22)
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- White light emission in water through admixtures of donor-π-acceptor siblings: Experiment and simulation
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Donor-acceptor π-conjugated molecules with triphenylamine donor and different acceptor (H, cyano, and pyridinium) units with a double bond spacer were synthesized. These compounds exhibit bathochromic shifts in absorption and emission with an increase in the acceptor strength. Solvatochromic measurements in water reveal emitting states characterized by a polar nature with three distinct emission spectral regions from blue to red. Interestingly, binary mixtures of the stilbenes in acetonitrile and water gave white light emission. MD simulations of the admixtures reveal that the emission data directly correlate to the structural arrangements of the molecules driven by intermolecular and solvent interactions with micelle-like structural arrangements for one set and uniform homogenous mixing for the other two sets. Such a tunable emission strategy using simple structural siblings could offer great potential towards designing novel emitting systems.
- Kumari, Beena,Singh, Amit,Jana, Palash,Radhakrishna, Mithun,Kanvah, Sriram
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p. 11701 - 11709
(2019/07/31)
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- Nickel-Catalyzed Decarboxylation of Aryl Carbamates for Converting Phenols into Aromatic Amines
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Herein, we describe a new catalytic approach to accessing aromatic amines from an abundant feedstock, namely phenols. The most reliable catalytic method for converting phenols to aromatic amines uses an activating group, such as a trifluoromethane sulfonyl group. However, this activating group is eliminated as a leaving group during the amination process, resulting in significant waste. Our nickel-catalyzed decarboxylation reaction of aryl carbamates forms aromatic amines with carbon dioxide as the only byproduct. As this amination proceeds in the absence of free amines, a range of functionalities, including a formyl group, are compatible. A bisphosphine ligand immobilized on a polystyrene support (PS-DPPBz) is key to the success of this reaction, generating a catalytic species that is significantly more active than simple nonsupported variants.
- Nishizawa, Akihiro,Takahira, Tsuyoshi,Yasui, Kosuke,Fujimoto, Hayato,Iwai, Tomohiro,Sawamura, Masaya,Chatani, Naoto,Tobisu, Mamoru
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supporting information
p. 7261 - 7265
(2019/05/16)
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- Rational Design of Dual-State Emission Luminogens with Solvatochromism by Combining a Partially Shared Donor–Acceptor Pattern and Twisted Structures
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We report a general design strategy for a new class of luminogens with dual-state emission (DSEgens) that are brightly emissive in both the solution and solid state, with solvatochromism properties, by constructing a partially shared donor–acceptor pattern based on a twisted molecule. The DSEgens with bright fluorescence emission in both the solid and solution state demonstrate a unique solvatochromism behaviour depending on solvent polarity and thus may have applications in anti-counterfeiting.
- Qiu, Qianqian,Xu, Pengfei,Zhu, Yanjun,Yu, Junru,Wei, Mengru,Xi, Wenbin,Feng, Hui,Chen, Jianrong,Qian, Zhaosheng
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p. 15983 - 15987
(2019/11/11)
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- Organic photoelectric compound and application thereof
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The invention provides an organic photoelectric compound and application thereof, and relates to the field of photoelectric materials. The organic photoelectric compound is provided with a pi-D-A structure, wherein pi is a conjugation unit, the conjugatio
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Paragraph 0061; 0069; 0070; 0071
(2019/01/05)
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- Cyano three aniline organic small molecule red light material and its synthesis and use
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The invention discloses a cyanotriphenylamine organic small molecular red emitting material, a synthesis method and use thereof. The synthesis method includes: taking triphenylamine as the raw material to react with POCl3 to synthesize an intermediate 4-(diphenylamino)benzaldehyde; subjecting the 4-(diphenylamino)benzaldehyde to reaction to obtain 4-bis(4-iodophenyl)aminobenzaldehyde; reacting the 4-bis(4-iodophenyl)aminobenzaldehyde with diphenylamine to obtain 4-(bis-(4-(diphenylamino)phenyl)amino)benzaldehyde and 4-((4-( diphenylamino)phenyl)(4-iodophenyl)amino)benzaldehyde; and reacting 4-(diphenylamino)benzaldehyde and the product of the last step respectively with malononitrile, cyano-acrylate or 2-(3, 5, 5-trimethylcyclohexenyl-2-octenylidene)malononitrile to obtain a novel cyanotriphenylamine compound. The invention preliminarily studies the relevant optical properties of the product, and lays the foundation for development of the product into a novel red emitting material with excellent performance.
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Paragraph 0063; 0067-0069
(2018/05/16)
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- Organic dye having a D-pi-A structure, a preparing method thereof and a dye-sensitized solar cell
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Organic dye having a D-pi-A structure, a preparing method thereof and a dye-sensitized solar cell are disclosed. The dye having the D-pi-A structure adopting benzopyranyl as a pi-bridge group, adopting a 2-cyano-acrylic acid group as an electron drawing group and adopting a triphenylamine group as an electron-donating group has a strong electron pushing-pulling system, effectively achieves electron separation in dye molecules, and has a high molar extinction coefficient and a wide spectral response range, and the photoelectric conversion efficiency is 6.7%. The triphenylamine group adopted asthe electron-donating group has a propeller type non-planar space structure, can reduce aggregation of sensitizing dye molecules on the surface of titanium dioxide film, enhances electron donating capability of the electron-donating group, reduces a forbidden band width of the dye and improves hole transporting capability. The benzopyranyl adopted as the pi-bridge group has a good conjugated structure, enhances conjugated effects of the dye molecules, and broadens the response range of absorption spectrums. The dye has good optical stability and thermal stability, is low in cost and has a wideapplication prospect.
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Paragraph 0028
(2018/05/30)
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- Antibacterial activities of mono-, di- and tri-substituted triphenylamine-based phosphonium ionic liquids
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We report the synthesis of new mono, di and tri phosphonium ionic liquids and the evaluation of their antibacterial activities on both Gram-positive and Gram-negative bacteria from the ESKAPE-group. Among the molecules synthesized some of them reveal a st
- Brunel, Frédéric,Lautard, Christelle,di Giorgio, Carole,Garzino, Frédéric,Raimundo, Jean-Manuel,Bolla, Jean-Michel,Camplo, Michel
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supporting information
p. 926 - 929
(2018/03/06)
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- D-D-pi-A structured photosensitive dye using carbazole and triphenylamine as two-stage electron donors, and preparation method and application thereof
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The invention discloses a D-D-pi-A structured photosensitive dye using carbazole and triphenylamine as two-stage electron donors. The photosensitive dye uses triphenylamine and carbazole as electron donors, 3,4-ethylenedioxythiophene or thiophene as a pi conjugated bridge and cyanoacetic acid as an electron acceptor. The invention also provides a preparation method of the photosensitive dye, and an application of the photosensitive dye in dye-sensitized solar cells. The photosensitive dye has various structures, and has a photoelectric conversion efficiency reaching up to 6%, and the preparation method has the advantages of simplicity, easiness in process control, low cost, and friendliness to the environment. The preparation method is suitable for preparing the D-D-pi-A structured photosensitive dye using carbazole and triphenylamine as two-stage electron donors, and the prepared photosensitive dye is suitable for being applied to the dye-sensitized solar cells.
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Paragraph 0163; 0166; 0168; 0169
(2018/11/03)
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- Two-photon fluorescent probe for secondarily recognizing copper ions and Hcy and preparation method of two-photon fluorescent probe
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The invention discloses a two-photon fluorescent probe for secondarily recognizing copper ions and Hcy and a preparation method of the two-photon fluorescent probe. The preparation method comprises the following steps of by taking triphenylamine as a matr
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Paragraph 0035; 0041; 0042; 0063
(2018/09/11)
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- A Multiple Stimuli-Sensitive Low-Molecular-Weight Gel with an Aggregate-Induced Emission Effect for Sol–Gel Transition Detection
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A low-molecular-weight gel (LMWG) with a hydrazone moiety and an aggregate-induced emission (AIE) unit was fabricated; the self-assembly and disassembly of the LMWG under different stimuli conditions were studied. The LMWG exhibited multiple stimuli sensitivity with temperature, light, ions, and ionic strength. The hydrazone was integrated into the gelator to act as ion sensing sites and hydrogen bond donor groups to fulfil the task of ion recognition of Ni2+, BH4 ?, and OH?, as well as ion-controlled reversible sol–gel recovery by adding H+ for deprotonation; it also broke under UV irradiation to evoke light-sensitivity. In addition, the sol–gel transition of the gel was detected by the AIE effect. The research provided an effective strategy in fabricating multiple stimuli-sensitive LMWGs for potential biomedical applications.
- Wang, Hao,Liu, Qihong,Hu, Yalong,Liu, Miaochang,Huang, Xiaobo,Gao, Wenxia,Wu, Huayue
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p. 457 - 462
(2018/07/06)
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- Molecular engineering of triphenylamine based aggregation enhanced emissive fluorophore: Structure-dependent mechanochromism and self-reversible fluorescence switching
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Triphenylamine (TPA), a propeller-shaped optoelectronic molecule, has been used to generate stimuli-responsive smart fluorescent organic materials and correlate the effect of subtle structural changes on the molecular packing and mechanochromic fluorescen
- Hariharan, Palamarneri Sivaraman,Prasad, Viki Kumar,Nandi, Surajit,Anoop, Anakuthil,Moon, Dohyun,Anthony, Savarimuthu Philip
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p. 146 - 155
(2017/12/02)
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- Dipolar vinyl sulfur fluorescent dyes. Synthesis and photophysics of sulfide, sulfoxide and sulfone based D-π-A compounds
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New vinyl sulfides and sulfoxides were obtained in good yields using the Horner-Wadsworth-Emmons (HWE) reaction. The vinyl sulfides and sulfoxides presented preferentially the E-stereochemistry. The respective vinyl sulfones were obtained in good yields from the vinyl sulfides by a simple oxidation step using mCPBA, solely as the E isomers. These derivatives presented absorption maxima in the UV-A region with molar absorptivity coefficients and radiative rate constant values ascribed to spin and symmetry-allowed 1π-π* electronic transitions. Experimentally, a small solvatochromic effect indicated an almost absent charge transfer character in the ground-state. A fluorescence emission in the violet-green region with a significative redshift on the maxima with increasing solvent polarity was observed, which could be related to a better electron delocalization in the excited state, as a result of an intramolecular charge transfer state. DFT and TD-DFT calculations were performed at the PBE1PBE and CAM-B3LYP levels of theory. No solvatochromic effect was observed in the ground state, but a bathochromic effect was detected in the emission maxima. Starting from sulfides to sulfones, the addition of oxygen atoms improved the charge separation, enabling an ICT state, mainly in P3 and P5. This charge separation was more efficient in the triphenylamino derivatives than among the pyrene derivatives since the first one has a better electron-donating character.
- Mon?alves, Matias,Zanotto, Gabriel M.,Toldo, Josene M.,Rampon, Daniel S.,Schneider, Paulo H.,Gon?alves, Paulo F. B.,Rodembusch, Fabiano S.,Silveira, Claudio C.
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p. 8832 - 8842
(2017/02/10)
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- With piezochromic characteristic ion iridium complex and its preparation method and application
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The invention relates to an ionic type iridium complex with piezochromic characteristic as well as a preparation method and application thereof and in particular relates to an ionic type iridium complex (III) based on 1,3,4-oxadiazole N^N auxiliary ligand, wherein a structural formula of the ionic type iridium complex is shown as a formula (I) or a formula (II) in the specification. Synthesis steps of the ionic type iridium complex are simple, synthesis conditions are mild, and luminescence of an organic luminophor in a solid state is changed by virtue of external factors of heat, light, electricity, pressure and the like, wherein the phenomenon that the luminescence of the solid organic luminophor is changed by adopting a pressure or mechanical grinding manner is called as a piezochromic phenomenon. A piezochromic material has unique emitting colour changing and reversing properties, so that the ionic type iridium complex has great potential in application of record, data storage, sensors and the like.
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Paragraph 0045; 0046
(2017/06/30)
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- Facile fabrication of AIE/AIEE-active fluorescent nanoparticles based on barbituric for cell imaging applications
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Four barbituric derivatives (1-4), were synthesized with obvious aggregation induced emission (AIE) or aggregation induced emission enhancement (AIEE) behaviors. The optical properties in different states and the mechanisms of the enhanced emission of 1-4 were investigated. We found that there were a large number of globular or blocky nanoparticles with average diameters from 229 to 394 nm in tetrahydrofuran (THF)/water solutions when the water fraction (fw) was 90%. The single crystal data of 2 and 4 reveal that multiple intermolecular interactions restrict the intramolecular motions, and promote the formation of a herringbone arrangement (4), thus permitting intense emission in the aggregate state. In addition, the frontier molecular orbital energy and band gap calculated by density functional theory (DFT) are consistent with the experimental results. Compound 4 is cell-permeable: upon entering the live cells, the dye molecules can accumulate in the lysosomes and turn on the fluorescence.
- Li, Kai,Zhang, Yang,Qiao, Bing,Tao, Furong,Li, Tianduo,Ding, Yunqiao,Raymo, Fran?isco M.,Cui, Yuezhi
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p. 30229 - 30241
(2017/07/07)
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- Synthesis and characterization of triphenylamine modified azobenzene dyes
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A series of triphenylamine modified azobenzenes were synthesized and studied theoretically and experimentally. D-A-D structures of these dyes were revealed with an intramolecular charge transfer (ICT) from both triphenylamine or indoline units (donor) to
- Zhao, Chuanwu,Wang, Tianyang,Li, Dongmei,Lu, Ting,Liu, Dongzhi,Meng, Qingbo,Zhang, Qianqian,Li, Fengqing,Li, Wei,Hu, Wenping,Wang, Lichang,Zhou, Xueqin
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p. 256 - 264
(2016/11/09)
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- BSA-coated fluorescent organic-inorganic hybrid silica nanoparticles: preparation and drug delivery
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It is desirable to engineer bio-compatible construction materials and cargo release vehicles with efficient cargo loading capability and controlled drug delivery ability. Herein, an inorganic-organic hybrid composite DNDT&SiO2-NH2@BS
- Yang, Zengming,Ma, Hengchang,Jin, Zijie,Cao, Haiying,Lei, Lei,Ma, Yucheng,Lei, Ziqiang
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supporting information
p. 1637 - 1644
(2017/02/23)
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