n-Butyllithium (2.5 M in hexane), 3,4-ethylenedioxythiophene (97%), bis(triphenylphosphine)palladium (II) dichloride (98%) were purchased from Aldrich. Selenophene (98.0%) and 5-(4,4,5,5-tetramrthyl-1,3,2-dioxaborolan-2-yl-2,2′-bithiophene (98%), were purchased from TCI Europe. Anhydrous potassium carbonate (99%) was received from Chempur. Anhydrous tetrahydrofuran was purchased from POCH. Tetrahydrofuran was dried over Na/benzophenone ketal before use. Other commercially available substances and reagents were used without the prior purification. Preparative column chromatography was performed on the glass column with Acros Organics silica gel for chromatography, 0.035–0.075 mm; 60 Å. The 600 MHz 1H NMR and 13C NMR spectra were recorded in deuterated chloroform (CDCl3) on Bruker Avance II 600 Instruments, respectively. Chemical shifts were locked to chloroform δH 7.26 (s) and δC 77.16 (t) signals.
Bis triphenylphosphine palladium 2 dichloride
Manufactured by Merck Group
Sourced in United States, Germany
Bis(triphenylphosphine)palladium(II) dichloride is a coordination complex composed of a palladium(II) center bound to two triphenylphosphine ligands and two chloride ligands. It is a commonly used precursor for palladium-catalyzed organic reactions.
Automatically generated - may contain errors
Lab products found in correlation
Anhydrous potassium carbonate, by Chempur (2 mentions)
Avance 2 600 instruments, by Bruker (2 mentions)
N butyllithium, by Merck Group (2 mentions)
4 bromobenzaldehyde, by Merck Group (2 mentions)
Ethanol, by Merck Group (2 mentions)
1 octene, by Merck Group (2 mentions)
Copper 1 iodide, by Merck Group (2 mentions)
Toluene, by Merck Group (2 mentions)
Methanol, by Daejung Chemicals (2 mentions)
Tetrakis triphenylphosphine palladium 0, by Merck Group (2 mentions)
Chloroform, by Merck Group (2 mentions)
3 4 ethylenedioxythiophene, by Merck Group (1 mentions)
P toluenesulfonic acid, by Merck Group (1 mentions)
N butyllithium solution, by Merck Group (1 mentions)
2 4 dimethylpyrrole, by Merck Group (1 mentions)
5 formyl 2 thienylboronic acid, by Merck Group (1 mentions)
Vnmrj600 nuclear magnetic resonance spectrometer, by Agilent Technologies (1 mentions)
Q exactive orbitrap device, by Thermo Fisher Scientific (1 mentions)
Quantaurus qy absolute pl quantum yield spectrometer, by Hamamatsu Photonics (1 mentions)
Cary eclipse fluorescence spectrophotometer, by Agilent Technologies (1 mentions)
9 protocols using bis triphenylphosphine palladium 2 dichloride
1
Synthesis of Conjugated Thiophene Derivatives
2
Synthesis of Functionalized Silanes
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n-Butyllithium solution (2 M in cyclohexane), dimethyldichlorosilane, diphenyldichlorosilane, bis(triphenylphosphine) palladium(ii ) dichloride, anhydrous N,N-dimethylacetamide (DMAc), anhydrous calcium chloride, p-toluenesulfonic acid, 1-fluoro-4-nitrobenzene, hydrazine monohydrate (80%) and Pd/C (10% w/w) were obtained from Aldrich Chemical (Milwaukee, WI, USA). 4-Hydroxyphenylboronic acid and 4-formylphenylboronic acid were purchased from AK Scientific, Inc. (San Francisco, USA). All other reagents and solvents were purchased commercially as analytical grade (Aldrich Chemical, WI, USA or Merck, Darmstadt, Germany). Immediately before use, diethyl ether was refluxed with sodium under nitrogen atmosphere and then distilled.
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n-Butyllithium solution (2 M in cyclohexane), dimethyldichlorosilane, diphenyldichlorosilane, bis(triphenylphosphine) palladium(
3
Synthesis and Characterization of Thiophene-Pyrrole Dyes
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2,4-Dimethylpyrrole
(≥ 97.0, Sigma-Aldrich), 4-bromobenzaldehyde (≥ 99.0,
Sigma-Aldrich), trifluoroacetic acid (≥ 99.0, Sigma-Aldrich),
DDQ (≥ 98.0, Sigma-Aldrich), boron trifluoride diethyl etherate
(≥ 98.0, TCI), 5-formyl-2-thienylboronic acid (≥ 95.0,
Sigma-Aldrich), bis(triphenylphosphine)palladium(II) dichloride (≥
98.0, Sigma-Aldrich), n-hexane (HPLC grade, ≥ 99.0, Sigma-Aldrich),
dichloromethane (anhydrous, ≥ 99.9, Sigma-Aldrich), acetonitrile
(anhydrous, ≥ 99.9, Sigma-Aldrich), ethanol (≥ 99.8,
Sigma-Aldrich), chloroform (≥ 99.8, Sigma-Aldrich), and ethyl
acetate (anhydrous, ≥ 99.8, Sigma-Aldrich) were used. All metal
salts were used as their water-soluble sulfate, nitrate, or chloride
salts, purchased from Sigma-Aldrich (≥ 95). A Varian VNMRJ
600 nuclear magnetic resonance spectrometer was used for 1H NMR and 13C NMR measurements. Mass analysis was conducted
with a Thermo Q-Exactive Orbitrap device. Ultraviolet–visible
(UV–vis) absorption spectra were obtained with a spectrophotometer
(Shimadzu 1900i). Fluorescence emission measurements were obtained
using a Varian Cary Eclipse fluorescence spectrophotometer. Quantum
yield measurements were conducted with a Hamamatsu Quantaurus-QY absolute
PL quantum yield spectrometer.
(≥ 97.0, Sigma-Aldrich), 4-bromobenzaldehyde (≥ 99.0,
Sigma-Aldrich), trifluoroacetic acid (≥ 99.0, Sigma-Aldrich),
DDQ (≥ 98.0, Sigma-Aldrich), boron trifluoride diethyl etherate
(≥ 98.0, TCI), 5-formyl-2-thienylboronic acid (≥ 95.0,
Sigma-Aldrich), bis(triphenylphosphine)palladium(II) dichloride (≥
98.0, Sigma-Aldrich), n-hexane (HPLC grade, ≥ 99.0, Sigma-Aldrich),
dichloromethane (anhydrous, ≥ 99.9, Sigma-Aldrich), acetonitrile
(anhydrous, ≥ 99.9, Sigma-Aldrich), ethanol (≥ 99.8,
Sigma-Aldrich), chloroform (≥ 99.8, Sigma-Aldrich), and ethyl
acetate (anhydrous, ≥ 99.8, Sigma-Aldrich) were used. All metal
salts were used as their water-soluble sulfate, nitrate, or chloride
salts, purchased from Sigma-Aldrich (≥ 95). A Varian VNMRJ
600 nuclear magnetic resonance spectrometer was used for 1H NMR and 13C NMR measurements. Mass analysis was conducted
with a Thermo Q-Exactive Orbitrap device. Ultraviolet–visible
(UV–vis) absorption spectra were obtained with a spectrophotometer
(Shimadzu 1900i). Fluorescence emission measurements were obtained
using a Varian Cary Eclipse fluorescence spectrophotometer. Quantum
yield measurements were conducted with a Hamamatsu Quantaurus-QY absolute
PL quantum yield spectrometer.
4
Synthesis of Conjugated Polymers
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Toluene
(anhydrous, 99.8%),
mEthanol (anhydrous, 99.8%), borane–tetrahydrofuran complex
solution 1 M in tetrahydrofuran (BH3OC4H8, 1 M in tetrahydrofuran), 1,4-diethynylbenzene (C8H6, 96%), 1-octene (C10H6, 96%),
silica-gel [(40–63) μm], magnesium sulfate (MgSO4, anhydrous, >99.0%), 2,5-dibromo-3-hexylthiophene (97%),
bis(triphenylphosphine)palladium(II) dichloride (Pd(PPh3)2Cl2, 98%), copper(I) iodide (CuI, >98.0%),
and triethylamine (TEA) (N(C2H5)3, 99.0%) were purchased from Sigma-Aldrich. Ethanol (C2H5OH, 99.5%), n-hexane (C7H16, 95%), mEthanol (CH3OH, 99.5%), and chloroform
(CHCl3, 99.7%) were purchased from Dae-Jung (South Korea),
and hydrofluoric acid [(48–51)%] was purchased from J.T. Baker.
(anhydrous, 99.8%),
mEthanol (anhydrous, 99.8%), borane–tetrahydrofuran complex
solution 1 M in tetrahydrofuran (BH3OC4H8, 1 M in tetrahydrofuran), 1,4-diethynylbenzene (C8H6, 96%), 1-octene (C10H6, 96%),
silica-gel [(40–63) μm], magnesium sulfate (MgSO4, anhydrous, >99.0%), 2,5-dibromo-3-hexylthiophene (97%),
bis(triphenylphosphine)palladium(II) dichloride (Pd(PPh3)2Cl2, 98%), copper(I) iodide (CuI, >98.0%),
and triethylamine (TEA) (N(C2H5)3, 99.0%) were purchased from Sigma-Aldrich. Ethanol (C2H5OH, 99.5%), n-hexane (C7H16, 95%), mEthanol (CH3OH, 99.5%), and chloroform
(CHCl3, 99.7%) were purchased from Dae-Jung (South Korea),
and hydrofluoric acid [(48–51)%] was purchased from J.T. Baker.
5
Synthesis and Purification of Organometallic Compounds
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Solvents of p.a. quality (per analysis) were commercially acquired from Sigma Aldrich, Carl Roth, or Acros Fisher Scientific and unless otherwise stated, used without further purification. Anhydrous solvents were purchased from Carl Roth, Acros, or Sigma Aldrich (less than 50 ppm of H2O, kept over molecular sieves). 2-Bromo-6-methylpyridine (98%) and benzyl azide (94%) were bought from Alfa Aesar. Propargyl alcohol (98%), butynyl alcohol (97%), bis(triphenylphosphine)palladium(II) dichloride (98%), and chloro(pentamethylcyclopentadienyl)(cyclooctadiene)ruthenium(II) (99.5%) were purchased from Sigma Aldrich.
Reaction mixtures were purified by flash chromatography. For the stationary phase of the column, silica gel, produced by Merck (silica gel 60, 0.040 × 0.063 mm, 260–400 mesh ASTM) and sea sand by Riedel de Haën (baked out and washed with hydrochloric acid) were used.
Air- and moisture-sensitive reactions were carried out under argon atmosphere in previously baked out apparatuses with standard Schlenk techniques. Liquid reagents and solvents were injected with syringes and stainless-steel cannulas of different sizes.
Reaction mixtures were purified by flash chromatography. For the stationary phase of the column, silica gel, produced by Merck (silica gel 60, 0.040 × 0.063 mm, 260–400 mesh ASTM) and sea sand by Riedel de Haën (baked out and washed with hydrochloric acid) were used.
Air- and moisture-sensitive reactions were carried out under argon atmosphere in previously baked out apparatuses with standard Schlenk techniques. Liquid reagents and solvents were injected with syringes and stainless-steel cannulas of different sizes.
6
Synthesis of Conjugated Polymer Electrodes
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All chemical reagents were
used as received without further purification. Toluene (anhydrous,
99.8%), borane–tetrahydrofuran complex solution (BH3OC4H8, 1.0 M in THF), 1,4-diethynylbenzene
(C10H6, 96%), 1-octene (C10H16, 98%), bis(triphenylphosphine)palladium(II) dichloride (Pd-(PPh3)2Cl2, 98%), copper(I) iodide (CuI,
>98.0%), triethylamine (TEA) (N(C2H5)3, 99.0%), vinylene carbonate (VC) (99%), sodium chloride (NaCl)
(≥98.0%),
and poly(acrylic acid) (PAA) (average Mv ∼ 450 000) were purchased from Sigma-Aldrich. Hydrofluoric
acid (HF, 48–51%) and ammonium hydroxide solution (NH4OH, 25%) were purchased from J.T. Baker and Acros Organic, respectively.
Super P carbon black, n-methyl-2-pyrrolidone (NMP),
Cu-foil, and Li-metal were obtained from Wellcos Corporation (South
Korea). Ethanol (EtOH) (C2H5OH, 99.5%) and methanol
(MeOH) (CH3OH, 99.5%) were purchased from Dae-Jung (South
Korea). 1-Bromo-4-ethynylbenzene (C8H5Br, >98.0%)
was purchased from TCI. One molar lithium hexafluorophosphate (LiPF6) in ethylene carbonate (EC)/ethyl methyl carbonate (EMC)
(1:1 v/v) was obtained from Soul-Brain (South Korea).
used as received without further purification. Toluene (anhydrous,
99.8%), borane–tetrahydrofuran complex solution (BH3OC4H8, 1.0 M in THF), 1,4-diethynylbenzene
(C10H6, 96%), 1-octene (C10H16, 98%), bis(triphenylphosphine)palladium(II) dichloride (Pd-(PPh3)2Cl2, 98%), copper(I) iodide (CuI,
>98.0%), triethylamine (TEA) (N(C2H5)3, 99.0%), vinylene carbonate (VC) (99%), sodium chloride (NaCl)
(≥98.0%),
and poly(acrylic acid) (PAA) (average Mv ∼ 450 000) were purchased from Sigma-Aldrich. Hydrofluoric
acid (HF, 48–51%) and ammonium hydroxide solution (NH4OH, 25%) were purchased from J.T. Baker and Acros Organic, respectively.
Super P carbon black, n-methyl-2-pyrrolidone (NMP),
Cu-foil, and Li-metal were obtained from Wellcos Corporation (South
Korea). Ethanol (EtOH) (C2H5OH, 99.5%) and methanol
(MeOH) (CH3OH, 99.5%) were purchased from Dae-Jung (South
Korea). 1-Bromo-4-ethynylbenzene (C8H5Br, >98.0%)
was purchased from TCI. One molar lithium hexafluorophosphate (LiPF6) in ethylene carbonate (EC)/ethyl methyl carbonate (EMC)
(1:1 v/v) was obtained from Soul-Brain (South Korea).
7
Synthesis of Organic Semiconductor Precursors
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n-Butyllithium (2.5 M in hexane), trimethyltin chloride (1.0 M in THF), 2-(tributylstannyl)pyridine (85%), 3,4-ethylenedioxytiophene (97%), selenophene (97%), 2-thienylboronic acid (95%), bis(triphenylphosphine)palladium (II) dichloride (98%), tetrakis(triphenylphosphine)palladium (0) (99%), and 4,7-bis(5-bromothiophen-2-yl)benzothiadiazole (99%) were purchased from Sigma Aldrich. Anhydrous potassium carbonate (99%) was received from Chempur. Anhydrous tetrahydrofuran, toluene, and methanol were purchased from POCH. Tetrahydrofuran was dried over Na/benzophenone ketal before use. Other commercially available substances and reagents were used without any prior purification. Preparative column chromatography was performed on the glass column with Acros Organics silica gel for chromatography, 0.035–0.075 mm, 60 Å. 1H-NMR and 13C-NMR spectra were recorded in deuterated chloroform (CDCl3) on Brüker Avance III 400 MHz Instruments or on Bruker Avance II 600 Instruments, respectively. Chemical shifts were locked to chloroform δH 7.26 (s) and δC 77.16 (t) signals. The molecular weights of the products were determined using a Brüker micrOTOF-Q spectrometer, FWHM-17500, 20 Hz (Billerica, MA, USA). The percentage composition of the elements was measured on a vario EL cube Analyzer from Elementar Americas (Ronkonkoma, New York, NY, USA).
8
Synthesis of Substituted Benzenes
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Tetraphenylmethane (95%, ABCR, Karlsruhe, Germany), 1,3,5-tribromobenzene (98%, Acros Organics, Geel, Belgium), bromine (99%, Acros Organics, Geel, Belgium) trimethylsilylacetylene (98%, ABCR, Karlsruhe, Germany), CuBr (98%, Sigma-Aldrich, Darmstadt, Germany), CuI (98%, Fluka, Dresden, Germany), tetrakis(triphenylphosphine)palladium(0) (99%, Sigma-Aldrich, Darmstadt, Germany), bis(triphenylphosphine)palladium(II) dichloride (98%, Sigma-Aldrich, Darmstadt, Germany), Bu4NF (1M solution in THF, ABCR, Karlsruhe, Germany), bis(4-bromophenyl)ether (99%, Sigma-Aldrich, Darmstadt, Germany), 1,4-diiodobenzene (98%, ABCR, Karlsruhe, Germany), phenylacetylene (98%, Acros Organics, Geel, Belgium), 1,3-diphenyl-2-propanone (99%, Sigma-Aldrich, Darmstadt, Germany), potassium hydroxide (99%, Acros Organics, Geel, Belgium), glacial acetic acid (99%, Sigma-Aldrich, Darmstadt, Germany), potassium permanganate, triethylamine (99%, Acros Organics, Geel, Belgium), toluene (99.5%, Component Reactive, Moscow, Russia), ethanol (96%, Component Reactive, Moscow, Russia), diphenylether (99%, ABCR, Karlsruhe, Germany), THF ( HPLC grade, Carlo Erba reagents, Milan, Italy), and gases: N2 (99.999%) and CO2 (99.999%) were used as received.
9
Novel Schiff Base Molecular Switch Synthesis
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Au (111) films on mica were purchased from Phasis, Switzerland. The STM tip was prepared from Pt/Ir wire cut under ambient conditions. All chemicals were used as received: chloroform (>99%, Merck), ethanol (>99%, Sigma-Aldrich), phenylacetylene (>98%, Sigma), ethynyltrimethylsilane (>98%, Sigma), 4-bromobenzaldehyde (>99%, Sigma), 4-aminobenzenethiol (>98%, Sigma), bis(triphenylphosphine)palladium(II) dichloride (>98%, Sigma-Aldrich), copper(I) iodide (>98%, Sigma), hexane (>98%, Sigma-Aldrich), and diethyl ether (99%, Sigma-Aldrich). Dichloromethane (CH 2 Cl 2 ) was dried over calcium hydride. THF was freshly prepared over Na metal in the presence of benzophenone as an indicator. Column chromatography was conducted with a silica gel 200-425 mesh. The structure of the prepared compounds was confirmed using 1 H NMR (500 MHz) and 13 C NMR (125 MHz).
The detailed procedures and characterization data for the prepared compounds are given in supporting information. Briefly, during the construction of novel Schiff base molecular switch EPBB, palladium/copper-catalyzed Sonogashira coupling between alkynylaryl and aryl halide which has an aldehyde moiety was conducted. Afterwards dehydration reaction between aldehyde and aminothiol yielded the product EPBB. The synthesis of the EPBB molecule depicted in figure 1 is described in the supporting information.
The detailed procedures and characterization data for the prepared compounds are given in supporting information. Briefly, during the construction of novel Schiff base molecular switch EPBB, palladium/copper-catalyzed Sonogashira coupling between alkynylaryl and aryl halide which has an aldehyde moiety was conducted. Afterwards dehydration reaction between aldehyde and aminothiol yielded the product EPBB. The synthesis of the EPBB molecule depicted in figure 1 is described in the supporting information.
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