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SENSORS AND ACTUATORS B-CHEMICAL · 2022 · IF 9.221

An ESIPT fluorescent probe based on Staudinger reaction for detection of triphenylphosphine and tetrakis(triphenyl-phosphine)palladium

Yuhuan Zhang,Hongjuan Li,Shiguo Sun,Yongqian Xu

Triphenylphosphine (PPh 3 ) and tetrakis(triphenylphosphine)palladium (Pd(PPh 3 ) 4 ) are harmful at extremely low concentration, thus it is essential to explore selective and sensitive method to detect them. Based on Staudinger reaction mechanism, here we present a simple excited-state intramolecular proton transfer (ESIPT) fluorescent probe (HBTN) for detection of PPh 3 and Pd(PPh 3 ) 4 over other phosphine derivatives with differential channel fluorescence (enol and keto emission). The reaction-typed fluorescence probe with novel Staudinger reaction mechanism offers very low autofluorescence and a large signal-to-noise response signal, which is beneficial for the sensitive detection of PPh 3 and Pd(PPh 3 ) 4 . Moreover, HBTN can be used for efficiently detecting Pd(PPh 3 ) 4 residues in highly purified products and imaging PPh 3 in living cells.

研究领域: 分析化学 · 生物医学
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Journal of Energy Chemistry · 2025 · IF 14.9

Importance of passivation efficiency of the passivator for efficient printable mesoscopic perovskite solar cells

Kangming Ou,Jiale Liu,Junwei Xiang,Chaoyang Wang,Jiayu Xie,Xiaoyu Li,Yanjie Cheng,Qiaojiao Gao,Lingya Gao,Anyi Mei,Yang Zhou,Hongwei Han

The stacking of multiple defect-rich grain boundaries (GBs) along the long transportation path (∼3 μm) of charge carriers in printable mesoscopic perovskite solar cells (p-MPSCs) impedes their power conversion efficiency (PCE). Organic Lewis bases are widely utilized for defect passivation at GBs, but how their passivation efficiency affects energy loss remains unclear. Here we employed triphenylphosphine (TPP) and triphenylphosphine oxide (TPPO) as the model passivators in p-MPSCs. TPPO has a more negatively charged center than TPP, which enables its stronger coordination with one of the most common and detrimental defects at the GBs—undercoordinated lead. When added into the perovskite with the same ratio, TPPO passivates defects more significantly and thus less TPPO remaining inactive compared with TPP. Inactive organic passivators accumulated at the GBs could impose barriers to charge carrier transportation. Indeed, TPPO improves the device performance more significantly with a champion PCE of 20.54% achieved. Besides, the TPPO devices demonstrate excellent stability with 95% of initial PCE remaining after 600 h of maximum power point tracking at (55 ± 5)°C.

CAS / MDL: 603-35-0
研究领域: 材料科学 · 能源科学
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ADVANCED FUNCTIONAL MATERIALS · 2019 ·Vol. 29 ·期 50 ·1906587 · IF 15.621

Perylene Diimide-Based Nonfullerene Polymer Solar Cells with over 11% Efficiency Fabricated by Smart Molecular Design and Supramolecular Morphology Optimization

Guangjun Zhang,Jirui Feng,Xiaopeng Xu,Wei Ma,Ying Li,Qiang Peng

A series of perylene diimide (PDI) derivatives, TPP-PDI , TPO-PDI , and TPS-PDI , are developed for nonfullerene polymer solar cells (NF-PSCs) by flaking three PDI skeletons around 3D central cores with different configurations and electronic states, such as triphenylphosphine (TPP), triphenylphosphine monoxide (TPO), and triphenylphosphine sulfide (TPS). These small-molecule acceptors have a “three-wing propeller” structure due to their similar backbones. By changing the electron density of phosphorus atoms through oxidation and sulfuration, the “folding-back” strength is decreased, resulting in a less twisted molecular conformation. The stronger electron-withdrawing ability of the oxygen atom affords TPO-PDI the least twisted conformation, which enhances the crystallinity of this complex. NF-PSCs based on PTTEA : TPO-PDI exhibit a high power conversion efficiency (PCE) of 8.65%. Ultimately, the joint “molecular lock” effect arising from O  H⋅⋅⋅F and O  H⋅⋅⋅OP supramolecular interactions is achieved by introducing 4,4′-biphenol as an additive, which successfully promotes fibril-like phase separation and blend morphology optimization to generate the highest PCE of 11.01%, which is currently the highest value recorded for NF-PSCs based on PDI acceptors.

研究领域: 材料科学 · 有机电子学 · 高分子化学 · 纳米技术 · 光化学
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JOURNAL OF CHEMICAL THERMODYNAMICS · 2022 · IF 3.269

Study on the solid-liquid equilibrium of triphenylphosphine in four mono-solvents and two mixed solvents

Shumin Xue,Jun Chu,Huanxin Yin,Xunqiu Wang

The gravimetric method was used to determine the solubility of triphenylphosphine in four mono-solvents (acetonitrile, tetrahydrofuran, cyclohexane, ethyl acetate) and two binary mixed solvents (acetonitrile + tetrahydrofuran, ethyl acetate + tetrahydrofuran) at normal pressure and temperature range (288.15 K-328.15 K). The results show that the solubility of triphenylphosphine in the selected solvent increased with the increase of temperature within the temperature range studied. In the binary mixed solvent (ethyl acetate + tetrahydrofuran, acetonitrile + tetrahydrofuran), the solubility of triphenylphosphine increased with the increase of the mass fraction of tetrahydrofuran. In addition, the Hansen solubility parameter (HSP) was used to explain the dissolution behavior of triphenylphosphine. The solubility data were fitted by the modified Apelblat equation, van't Hoff equation, λh equation, Apelblat-Sun equation and NRTL model. The results show that the modified Apelblat equation and van't Hoff equation have a better fitting effect on the solubility data of triphenylphosphine in the mono-solvents used in the experiment, and the modified Apelblat equation has a better fitting effect on the solubility data of triphenylphosphine in the binary mixed solvent used in the experiment. The fitting results can provide some basic data for the optimization of the crystallization process of triphenylphosphine. The thermodynamic properties of the dissolution process of triphenylphosphine in the selected solvent were calculated and discussed by van't Hoff equation, and the thermodynamic properties of the solution (Δ dis H , Δ dis S and Δ dis G ) were all positive values, which increased that the mixing and dissolution of triphenylphosphine in the selected solvent are endothermic and entropy-driven. This study can provide basic thermodynamic data for the crystallization and industrial separation of triphenylphosphine.

CAS / MDL: 109-99-9 603-35-0
研究领域: 化学工程 · 物理化学
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ADVANCED FUNCTIONAL MATERIALS · 2025 · IF 19

Efficient Pure-Red Tin-Based Perovskite Light-Emitting Diodes Enabled by Multifunctional Lewis-Base Additives

Jiaxing Zhu,Ciyu Ge,Borui Jiang,Xiang Zhang,Jiajun Luo,Jiang Tang

Tin-halide perovskites (THPs) offer a promising alternative to lead-halide perovskites (LHPs), addressing environmental concerns while providing excellent optoelectronic properties. However, the performance of THP light-emitting diodes (LEDs) remains inferior to their lead-halide counterparts due to challenges such as Sn 2 ⁺ oxidation, rapid crystallization, and high defect densities. Here, for the first time, a multifunctional Lewis-base reducing ligand triphenylphosphine (TPP) is reported, which simultaneously suppresses Sn 2+ oxidation and passivates defects in 2D THPs TEA 2 SnI 4 (TEA represents 2-thienylethylamine). The P atom in TPP, with its lone pair electrons on the 3p orbital, has low electronegativity and high electron density, which can effectively suppress Sn 2+ oxidation. Furthermore, σ-donation and π-conjugation effects from the three phenyl groups in the TPP molecule enable it to strongly coordinate with Sn 2+ , which passivates defects in TEA 2 SnI 4 . These properties enhance the stability and optoelectronic properties of THPs. When the optimized THP films are implemented as active layers in LEDs, they exhibit a narrow electroluminescence full-width at half-maximum of 28 nm, Commission Internationale de l'Eclairage x-coordinate exceeding 0.7, and a peak external quantum efficiency of 10.12%, sevenfold higher than the pristine devices. This work demonstrates the potential of molecular additives to enhance the device performance of tin-based perovskites.

研究领域: 材料科学 · 光电子学
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INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES · 2025 ·Vol. 26 ·期 11 ·5280 · IF 4.9

Design, Synthesis, Anti-Tumor Activity and Molecular Docking Studies of Novel Triphenylphosphine-Containing Formononetin Derivatives

Hongjuan Cui,Yan Zhao,Wei Li,Huanjie Cui,Jiahong Han,Enbo Cai

Formononetin is widely used in anti-tumor research, but its poor water solubility leads to low absorption and poor utilization efficiency in vivo, limiting further development. The triphenylphosphine cation was partially attached to the 7-position hydroxyl group of formononetin to specifically target it into the mitochondria of tumor cells to enhance the anti-tumor effect. Detailed structural characterization via 1 H-NMR and 13 C-NMR analysis confirmed the physical properties and chemical structures of 21 newly synthesized derivatives. The effects of these derivatives on tumor cells were assessed by in vitro and computational methods. MTT results from four tumor cell lines showed that formononetin derivatives containing triphenylphosphine had stronger anti-tumor activity than formononetin and exhibited more cytotoxic effects in cancer cells than in normal cells. In particular, the final product 2c (IC 50 = 12.19 ± 1.52 μM) showed more potent anti-tumor activity against A549 cells. It was also superior to formononetin and 5-FU. To identify the potential biological targets, the core-expressed gene SHMT2 in lung cancer mitochondria was screened using network pharmacology technology, and molecular docking analysis confirmed the stable binding of the end products to the amino acid residues of the core genes through the formation of hydrogen bonds and via other interactions. In addition, molecular docking simulations further confirmed that the end product exhibited excellent stability when bound to SHMT2 . These results suggest that triphenylphosphine-containing formononetin derivatives are worthy of further exploration in the search for novel drug candidates for the treatment of cancer.

CAS / MDL: 51-21-8 67-68-5
研究领域: 药理学 · 肿瘤学 · 计算生物学
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CARBOHYDRATE POLYMERS · 2022 · IF 10.723

Conversion of azidoamylose to ureidoamylose carbamates in one-pot reactions

Jing Hu,Yu-Hang Zhang,Wei Chen,Zheng-Wu Bai

In order to covert azidoamylose into ureidoamylose derivatives in a facile way, 6-azido-6-deoxyamylose was reacted with triphenylphosphine , and then with water and a phenyl isocyanate in turn. The obtained product was amylose 2,3-bis(phenylcarbamate)-6-deoxy-6-(phenylurea), which was synthesized through three reactions in a one-pot method. The essential point to ensure the method be successful was that the water should be fed at an appropriate amount. The prepared amylose 2,3-bis(phenylcarbamate)-6-deoxy-6-(phenylurea)s were characterized by FT-IR, 1 H NMR and elemental analysis , substantiating the reduction of the azido group and the subsequent derivatization of the resulted amino group and the hydroxyl group in amylose were fully performed. In addition, the amylose 2,3-bis(phenylcarbamate)-6-deoxy-6-(phenylurea)s were coated on macroporous 3-aminopropyl silica gel to afford chiral stationary phases (CSPs) for high-performance liquid chromatography. The enantioseparations of the CSPs were evaluated, and the results indicated that the CSPs possessed chiral recognition ability towards some chiral compounds.

研究领域: 有机化学 · 高分子化学
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SEPARATION AND PURIFICATION TECHNOLOGY · 2023 · IF 8.6

Reversible ligand exchange of triphenylphosphine with thiols on gold nanoparticles for Janus modification and catalyst recycling

Degui Li,Tong Liu,Yujia Luo,Xiangqun Zhuge,Kun Luo,Zhihong Luo,Xiaoteng Liu,Kui Zhang

Separation and regeneration of ultrafine catalysts in reaction system still remain challenging. In this study, we demonstrate a simple route to recycle gold nanoparticle (Au NP) catalysts by alternating surface wettability. Hydrophilic Au NPs protected with 3-mercapto-1,2-propanediol (MPD) were applied to catalyze the reduction of 4-nitrophenol (4-NP) using sodium borohydride as reductant, and were then separated from the suspension by interfacial ligand exchange with a toluene solution containing triphenylphosphine (TPP), led to amphiphilic Janus Au NPs with both MPD and TPP ligands at the toluene-water interface. The catalyst was regenerated by a reversible ligand exchange with a MPD aqueous solution. Experiments show that interfacial ligand exchange between phosphines and thiols on gold surface is reversible, although the forward and backward rates are different. As a result, the Au NP catalyst capped with MPD exhibited an excellent catalytic activity with an apparent rate constant ( k ) of 2.79 min −1 , and the performance could be maintained for more than 10 regeneration cycles. The facile conversion between hydrophilic and amphiphilic Janus Au NPs provides a new pathway to explore monophasic and multiphasic reactions with convenient catalyst separation and regeneration.

CAS / MDL: 603-35-0 96-27-5
研究领域: 材料科学 · 催化化学 · 界面化学
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RUSSIAN JOURNAL OF COORDINATION CHEMISTRY · 2018 ·Vol. 44 ·期 7 ·454-459 · IF 0.674

Reactivity of Two 16e Half-Sandwich Cobalt Complexes Containing 1,2-Dicarba-closo-Dodecaborane-1,2-Dichalcogenolate (E2C2B10H10)2– (E = S, Se) Units toward Triphenylphosphine

Ye H. D.,Zhan Y. L.,Liang J.,Ye T. Y.,Zhang D.,Peng H. N.,Hu J. R.

Treatment of o -carborane, n -butyllithium, sulfur (or selenium) and MeCpCo(CO)I 2 (or Cp*Co(CO)I 2 ) (Cp* = pentamethylcyclopentadienyl) under argon leads to half-sandwich carborane complex MeCpCo(S 2 C 2 B 10 H 10 ) (I) (or Cp*Co(Se 2 C 2 B 10 H 10 ) ( II )). Complex I reacts with triphenylphosphine to afford addition product MeCpCo(S 2 C 2 B 10 H 10 )(PPh 3 ) ( III ). However, II does not react with triphenylphosphine. Complexes II and III have been characterized by elemental analysis, mass, NMR spectroscopy, IR and X-ray structural analyses (CIF files CCDC nos. 1571705 ( II ) and 1571706 ( III )).

CAS / MDL: 603-35-0
研究领域: 无机化学 · 配位化学
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RUSSIAN JOURNAL OF INORGANIC CHEMISTRY · 2025 · IF 1.5

Reactivity of Half-Sandwich 16-e Carborane Complex CpCo[S2C2B10H10] with Triarylphosphines

Wang L. C.,Ye H. D.,Xu C.,Peng H. N.,Zhang X. L.,Chen F. Y.,Peng S. Y.,Wang S. J.

o-Carborane reacts sequentially with n-butyllithium, sulfur and CpCo(CO)I2 under argon to give the half-sandwich 16-e carborane complex CpCo[S2C2B10H10]. CpCo[S2C2B10H10] reacts with PPh3, P(m-Tol)3, P(p-Tol)3 to afford addition products CpCo(PPh3)[S2C2B10H10] (1), Cp(P(m-Tol)3)Co[S2C2B10H10] (2), CpCo(P(p-Tol)3)[S2C2B10H10] (3), respectively. 1, 2 and 3 have been characterized by chemical analysis, mass-spectrometry, IR and NMR spectroscopy, and single crystal X-ray diffraction (CCDC nos. 2390939 (1), 2390940 (2) and 2390938 (3)).

研究领域: 无机化学 · 配位化学
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GOLD BULLETIN · 2020 ·Vol. 53 ·期 2 ·55-62 · IF 1.706

Synthesis of amphiphilic Janus gold nanoparticles stabilized with triphenylphosphine and D-penicillamine by ligand exchange at toluene/water emulsion interface

Li Degui,Luo Yujia,Lan Jiaxin,Luo Zhihong,Li Fujie,Luo Kun

Ligand exchange was triggered at toluene/water emulsion interface between homogeneous gold nanoparticles (Au NPs) with triphenylphosphine (PPh 3 ) and D-penicillamine (D-PA), resulted in amphiphilic Janus Au NPs with both phosphine and thiolate ligands. TEM and XRD analyses indicate that the product is composed of Au nanocrystals in an average diameter of about 3.7 nm. XPS, FTIR, Raman, and 1 H NMR analyses demonstrate that the Au NPs are protected with hydrophilic D-PA molecules and lipophilic PPh 3 ligands in a molecular ratio of ca. 1.8. The NOESY analysis and contact angle measurement further suggest that the D-PA and PPh 3 molecules are spontaneously separated to form compartmentalized hydrophilic and lipophilic regions on the individual Au NPs, which exhibit good catalytic performance and recyclability on the reduction of 4-nitrophenol. The results demonstrate that amphiphilic Janus Au NPs can be synthesized by partly exchange of PPh 3 with D-PA at toluene/water emulsion interface and are potentially applicable for other phosphine/thiolate pairs to modify Au NPs.

CAS / MDL: 603-35-0
研究领域: 材料科学 · 纳米技术 · 化学
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CURRENT ORGANIC SYNTHESIS · 2017 ·Vol. 14 ·期 8 ·1185-1192 · IF 1.917

Silver Chloride/Triphenylphosphine-Promoted Carboxylation of Arylboronic Esters with Carbon Dioxide at Atmospheric Pressure

Zhou Zhi-Hua,Guo Chun-Xiang,Xie Jia-Ning,Liu Kai-Xuan,He Liang-Nian

Aim and Objective: The carboxylation of organoboronic esters with CO2 is an attractive way of preparing the functionalized carboxylic acid derivatives. For the silver-catalyzed carboxylation of arylboronic esters with CO2, sensibility of catalytic system to CO2 pressure resulted in a high CO2 pressure required in the reaction. This work focuses on solving this problem and promoting this transformation under atmospheric CO2 pressure. Material and Method: Arylboronic esters were synthesized according to the published procedure. Arylorganic esters, silver compound, base, PPh3 and solvent were introduced into a 25 mL Schlenk flask. Then, the gasexchanging operation via a “freeze-pump-thaw” method was conducted. After being enclosed with a CO2 balloon, the resulting mixture was stirred at 70oC for 12 h. Then, the reaction was quenched by 1 M HCl and extracted with ethyl acetate. The yields of the corresponding carboxylic acids were determined by GC. The structures of products were confirmed by NMR and GC-MS. Results: The carboxylation of arylboronic esters with ambient CO2 was achieved on the basis of the silver chloride/triphenylphosphine system by using cesium carbonate as the base and dimethyl sulfoxide as the solvent. Through this protocol, various functionalized carboxylic acids were synthesized in 85-99% yields. Conclusion: The silver-catalyzed carboxylation of arylboronic esters with ambient CO2 was established. This approach represents an alternative way to prepare carboxylic acids derivatives from the organoboron compounds with CO2 under mild reaction conditions.

研究领域: 有机化学 · 环境化学
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