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Tetrakis triphenylphosphine palladium

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Tetrakis(triphenylphosphine)palladium is a coordination complex consisting of a palladium atom coordinated to four triphenylphosphine ligands. It is a yellow crystalline solid commonly used as a catalyst in organic synthesis reactions.

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Lab products found in correlation

Dimethyl sulfoxide (dmso), by Merck Group (2 mentions) Copper iodide, by Merck Group (1 mentions) Tetrabutylammonium hydroxide, by Merck Group (1 mentions) Phenylboronic acid, by Merck Group (1 mentions) Potassium tert butoxide, by Merck Group (1 mentions) Nickel 2 nitrate hexahydrate, by Sinopharm (1 mentions) Gold trichloride, by Merck Group (1 mentions) Copper 2 nitrate trihydrate, by Sinopharm (1 mentions) Magnesium 2 nitrate hexahydrate, by Sinopharm (1 mentions) Zinc 2 nitrate hexahydrate, by Sinopharm (1 mentions) Potassium carbonate, by Sinopharm (1 mentions) Sodium hydroxide (naoh), by Sinopharm (1 mentions) Iron 3 chloride hexahydrate, by Sinopharm (1 mentions) Sodium carbonate, by Sinopharm (1 mentions) Sodium nitrate, by Sinopharm (1 mentions) Potassium nitrate, by Sinopharm (1 mentions) 2 1 3 benzothiadiazole, by Merck Group (1 mentions) Phospho histone h2a x ser139, by Cell Signaling Technology (1 mentions) Mitotracker green fm, by Thermo Fisher Scientific (1 mentions) Bcl2 associated x (bax), by Cell Signaling Technology (1 mentions)

12 protocols using tetrakis triphenylphosphine palladium

1

Synthesis of Bromocarbazole-Triethynylbenzene

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2,7-Dibromocarbazole was purchased from Energy Chemical, Shanghai, China and 1,3,5-triethynylbenzene was received from TCI, Tokyo, Japan. Copper iodide and tetrakis (triphenylphosphine) palladium were obtained from Sigma-Aldrich, St. Louis, MO, USA. Other chemicals and solvents were purchased from commercial suppliers and used without further purification. All reactions were performed under a purified nitrogen atmosphere.
Yan Z., Cui B., Zhao T., Luo Y., Zhang H., Xie J., Li N., Bu N., Yuan Y, & Xia L. (2021). A Carbazole-Functionalized Porous Aromatic Framework for Enhancing Volatile Iodine Capture via Lewis Electron Pairing. Molecules, 26(17), 5263.
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2

Synthesis of Model Compound OPV

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The model compound OPV used in this work was synthesized via Knoevenagel condensation reaction (fig. S1). The starting reagents, 2,5-dibromobenzene-1,4-dicarbaldehyde and 4-(diphenylamino)benzaldehyde, were purchased from J&K Chemical Ltd. (Beijing, China) and purified by recrystallization. Phenylboronic acid, tetrakis(triphenylphosphine)palladium, potassium tert-butoxide, tetra-butyl ammonium hydroxide, and tosylmethyl isocyanide were purchased from Sigma-Aldrich and used without further treatment. Organic solvents—toluene, dichloromethane, chloroform, tetrahydrofuran, and methanol—were dried and distilled before use.
Wang K., Gao Z., Zhang W., Yan Y., Song H., Lin X., Zhou Z., Meng H., Xia A., Yao J, & Zhao Y.S. (2019). Exciton funneling in light-harvesting organic semiconductor microcrystals for wavelength-tunable lasers. Science Advances, 5(6), eaaw2953.
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3

Synthesis of Metal-Organic Frameworks

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All chemicals were used without further purification unless otherwise specified. p-Phenylenediamine, 4-bromobenzonitrile, and tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate were supplied by Energy Chemical. Gold trichloride and tetrakis(triphenylphosphine)palladium were bought from Sigma-Aldrich. 3,3′,5,5′-Azobenzene tetra carboxylic acid, trimesic acid, and terephthalic acid were purchased from Acmec. Sodium hydroxide, iron(III) chloride hexahydrate (97%), copper(II) nitrate trihydrate (99%), nickel(II) nitrate hexahydrate (99%), sodium nitrate (99%), magnesium(II) nitrate hexahydrate (99%), potassium nitrate, zinc(II) nitrate hexahydrate (99%), potassium carbonate, sodium carbonate, sodium sulfate, and all solvents were provided by Sinopharm Chemical Reagent Co. Ltd. The Yangtze River water was collected in Nanjing, China (latitude: 32.156613, longitude: 118.800723). The East China Sea water was collected in Xiamen, China (latitude: 24.442217, longitude: 118.075667).
Xue T., He T., Peng L., Syzgantseva O.A., Li R., Liu C., Sun D.T., Xu G., Qiu R., Wang Y., Yang S., Li J., Li J.R, & Queen W.L. (2023). A customized MOF-polymer composite for rapid gold extraction from water matrices. Science Advances, 9(13), eadg4923.
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4

Synthesis of Tetrakis(Pinacolato)Pyrene and Dibromodibenzothiadiazole

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All reagents were used in the synthesis was utilized without further purification. Tetrakistriphenylphosphine)palladium (0) (99%) [1,1′bis (diphenylphosphino) ferrocene]dichloro palladium (II)], 2,1,3-benzothiadiazole (98%), were received from sigma Aldrich. Bis (PINACOLATO) DIBORON (>98%), K2CO3, HBr and Br2 solutions were purchased from Spectrochem, India. Other solvents were procured from local commercial sources. 1,3,6,8-tetrakis (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrene (PYTBE) and 4, 7-Dibromo-2,1,3-benzothiadiazole (DBrTDZ) were synthesized following the previously reported procedure (Bhunia et al., 2017 (link)).
Das S.K., Shyamal S., Das M., Mondal S., Chowdhury A., Chakraborty D., Dey R.S, & Bhaumik A. (2021). Metal-Free Pyrene-Based Conjugated Microporous Polymer Catalyst Bearing N- and S-Sites for Photoelectrochemical Oxygen Evolution Reaction. Frontiers in Chemistry, 9, 803860.
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5

Cellular Protein Interaction Analysis

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Iridium chloride hydrate, ammonium hexafluorophosphate, biotin, selenium dioxide, N-hydroxysuccinimide (NHS), and benzo[b]thiophen-2-ylboronic acid were obtained from commercial sources and used as received. Tetrakis(triphenylphosphine)palladium was from Sigma, USA, deuterated solvents were from CIL, USA, and MitoTracker™ Green FM was from Thermo, USA. All other chemicals and materials were used directly without further purification. The antibodies Bcl-2, Bax and phospho-histone H2A.X (Ser139) were purchased from Cell Signaling Technology.
Zhao Z., Gao P., Ma L, & Chen T. (2020). A highly X-ray sensitive iridium prodrug for visualized tumor radiochemotherapy. Chemical Science, 11(15), 3780-3789.
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6

Synthesis and Characterization of Alloc-KGDEVD Peptide

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Ac-K(Alloc)GD(All)E(All)VD(All)-OH (alloc-KGDEVD) was purchased from Peptron (Daejeon, Korea). Chlorin e6 (Ce6) was purchased from Frontier Scientific Inc. (Logan, UT, USA). 2-ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ), Bis(p-nitrophenyl) carbonate, 1-ethyl-3(3-dimethylaminopropyl) carbodiimide (EDC), Dimethyl sulfoxide (DMSO), N,N-diisopropylethylamine (DIPEA), hydroxybenzotriazole (HOBt), p-aminobenzyl alcohol, tetrakis(triphenylphosphine)palladium, and N-hydroxysuccinimide (NHS) were purchased from Sigma Chemical Co. (St. Louis, MO, USA). Anhydrous dimethylformamide (DMF) and dimethylsulfoxide (DMSO) were purchased from Merck (Darmstadt, Germany). Tributyltin hydride (Bu3SnH) and glacial acetic acid were purchased from Acros (St. Louis, MO, USA). DMEM medium, penicillin–streptomycin, and fetal bovine serum (FBS) were purchased from WelGENE Inc. (Daegu, Korea). Cathepsin B, D, K, L, caspase-9, caspase-3, and caspase-3 ELISA Kit (cat# SMIF00) were purchased from R&D system (Minneapolis, MN, USA). KPC960 (Human pancreatic cancer) cell lines were purchased from American Type Culture Collection (ATCC; Manassas, VA, USA). Tem grid (Carbon Film 200 Mesh copper) was purchased from Electron Microscopy Sciences (Hatfield, PA, USA). Cell counting kit-8 (CCK-8) was purchased from Vitascientific (Beltsville, MD, USA).
Cho I.K., Shim M.K., Um W., Kim J.H, & Kim K. (2022). Light-Activated Monomethyl Auristatin E Prodrug Nanoparticles for Combinational Photo-Chemotherapy of Pancreatic Cancer. Molecules, 27(8), 2529.
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7

Peptide Synthesis Protocol for Drug Discovery

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All chemicals, reagents, resins, and cell lines were obtained from commercial sources. Fmoc-protected amino acids, 2-(6-chloro-1H-benzotriazole-1-yl)-1,1,3,3-tetramethylaminium hexafluorophosphate (HCTU) and trifluoroacetic acid (TFA) were purchased from Advanced ChemTech, Louisville, KY. Chlorotrityl chloride resin (CTC) was purchased from ChemImpex, Wood Dale, IL. Diisopropylethylamine (DIEA), methanol (MeOH), chloroform, acetic acid, trifluoroethanol (TFE), tetrakis (triphenylphosphine) palladium, N-methyl morpholine (NMM), and 6-carboxyfluorescein (6-FAM) were purchased from Sigma-Aldrich, St. Louis, MO. Dimethylformamide (DMF), dichloromethane (DCM) and triisopropyl silane (TIPS) were purchased from Protein Technologies, Tucson, AZ. (7-Azabenzotriazol-1-yloxy) tripyrrolidinophosphonium hexafluorophosphate (PyAOP), (benzotriazol-1-yloxy) tripyrrolidinophosphonium hexafluorophosphate (PyBOP), and N-hydroxybenzotriazole (HOBT) were purchased from EMD Millipore, Billerica, MA. Cell lines and their respective media were purchased from the American Type Culture Collection (ATCC, Manassas, VA). CellTiter-Glo® reagent was purchased from Promega (Madison, WI).
Pallerla S., Naik H., Singh S., Gauthier T., Sable R, & Jois S.D. (2018). Design of cyclic and D-amino acids containing peptidomimetics for inhibition of protein-protein interactions of HER2-HER3. Journal of peptide science : an official publication of the European Peptide Society, 24(2), 10.1002/psc.3066.
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8

Synthesis of Polycyclic Aromatic Compounds

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Benzene-1,3,5-triyltriboronic acid pinacol ester and tris(4-boronic acid pinacol ester phenyl)amine were purchased from Sukailu, Suzhou, China. 2,7-dibromopyrene, chlorothalonil, nitrofen, trifluralin, and dicloran were all purchased from Aladdin, Shanghai, China. Potassium carbonate was obtained from Energy Chemical, Shanghai, China. Tetrakis(triphenylphosphine)palladium was obtained from Sigma-Aldrich, St. Louis, MO, USA. Other chemicals and solvents were purchased from commercial suppliers and used without further purification. All reactions were performed under a purified nitrogen atmosphere.
Yan Z., Liu J., Miao C., Su P., Zheng G., Cui B., Geng T., Fan J., Yu Z., Bu N., Yuan Y, & Xia L. (2021). Pyrene-Based Fluorescent Porous Organic Polymers for Recognition and Detection of Pesticides. Molecules, 27(1), 126.
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9

Synthesis of Polycyclic Aromatic Hydrocarbons

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1,3,5-Triethynylbenzene (TCI), 2,7-dibromo-9,10-phenanthrenedione (Energy Chemistry), 2,6-dibromoanthraquinone (Energy Chemistry), triethylamine (Energy Chemistry), anhydrous N,N′-dimethylformamide (Sinopharm Chemical Reagent Co., Ltd., Shanghai, China), cuprous iodide (Sigma-Aldrich, Darmstadt, Germany), tetrakis(triphenylphosphine)palladium (Sigma-Aldrich, Germany), and all other materials were obtained from commercial suppliers and used without further purification.
Yan Z., Qiao Y., Sun Q., Cui B., Feng B., Bu N., Chu K., Ruan X., Yuan Y., Yang Y, & Xia L. (2022). Introducing Polar Groups in Porous Aromatic Framework for Achieving High Capacity of Organic Molecules and Enhanced Self-Cleaning Applications. Molecules, 27(18), 6113.
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10

Synthesis of 2,5-dibromo-3-butylthiophene

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Tetrakis(triphenylphosphine)palladium ((PPh3)4Pd), copper(I) iodide (CuI), tetrahydrofuran (THF), diisopropylamine (i-Pr2NH), 2,5-dibromo-3-butylthiophene and all other chemicals were purchased from Sigma-Aldrich (St. Louis, MO, USA), Fisher Scientific (Pittsburgh, PA, USA), Alfa Aesar (Ward Hill, MA, USA) or Acros Organics (Morris Plains, NJ, USA) and used as received unless otherwise noted. For air-sensitive synthetic steps, solvents were freshly distilled and stored under a nitrogen atmosphere prior to use.
Chen A., Wu W., Fegley M.E., Pinnock S.S., Duffy-Matzner J.L., Bernier W.E, & Jones WE J.r. (2017). Pentiptycene-Derived Fluorescence Turn-Off Polymer Chemosensor for Copper(II) Cation with High Selectivity and Sensitivity. Polymers, 9(4), 118.
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