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CAS No. : | 1662-01-7 | MDL No. : | MFCD00004976 |
Formula : | C24H16N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DHDHJYNTEFLIHY-UHFFFAOYSA-N |
M.W : | 332.40 | Pubchem ID : | 72812 |
Synonyms : |
NSC 637659;BPhen
|
||
UV : | 272 nm (in THF) | ||
FL : | 379 nm (in THF) | Materials Type : | Other OLED Materials |
Num. heavy atoms : | 26 |
Num. arom. heavy atoms : | 26 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 107.92 |
TPSA : | 25.78 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -4.27 cm/s |
Log Po/w (iLOGP) : | 2.98 |
Log Po/w (XLOGP3) : | 5.71 |
Log Po/w (WLOGP) : | 6.12 |
Log Po/w (MLOGP) : | 4.28 |
Log Po/w (SILICOS-IT) : | 5.99 |
Consensus Log Po/w : | 5.02 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 1.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -6.11 |
Solubility : | 0.00026 mg/ml ; 0.000000783 mol/l |
Class : | Poorly soluble |
Log S (Ali) : | -6.02 |
Solubility : | 0.000319 mg/ml ; 0.00000096 mol/l |
Class : | Poorly soluble |
Log S (SILICOS-IT) : | -10.01 |
Solubility : | 0.0000000326 mg/ml ; 0.0000000001 mol/l |
Class : | Insoluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.21 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P264-P270-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | In N,N-dimethyl-formamide other Radiation; subjected to 300-W microwave irradn. at 250°C for 5 min; cooled, pptd. (CH2Cl2/Et2O), recrystd.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | In tetrahydrofuran; for 4h;Irradiation; | General procedure: 0.28mmol (100mg) of W(CO)6 were added into a one-neck round-bottom flask with 15mL of dried THF. Then, the solution was deaerated with argon for 15min. After degassing, the solution was irradiated for 40min with a 365nm led lamp. The solution changed from pale yellow to yellowish-green. A stoichiometric amount of 4,7-DMPhen with 5% excess was dissolved in THF into a separate container and degassed with argon for 15 to 30min. After that, the solution was carefully transferred dropwise with a syringe to the round-bottom flask. The resulting solution was irradiated for 4h forming a dark red solution. The product was then purified on a silica chromatographic column using ethyl acetate as eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | In 5,5-dimethyl-1,3-cyclohexadiene; for 2.5h;Reflux; | The fac-[Re(CO)3(Ph2-phen)Cl] complex was prepared using a slightmodification of the procedure previously described for similar compounds[49-51]. To xylene (100 mL), 4,7-diphenyl-1,10-phenanthroline,Ph2-phen, (1.08 g - 3.25 mmol) was added. The mixture wascontinuously stirred and heated to boiling, upon which the completedissolution of the ligand was observed. Next, Re(CO)5(Cl)(1.2 g-3.25 mmol) was added, and the mixture was refluxed for 2.5 h.After the solution had reached room temperature, the formation of asolid was observed, which was filtered and dried in a desiccator,yielding 1.69 g of product, corresponding to 86% yield. The spectroscopicdata for the product were coincident with those reported [52]. |
In 5,5-dimethyl-1,3-cyclohexadiene; for 6h;Reflux; | General procedure: Rhenium(I) compounds were synthesized following the procedure previously reported [15,16,39-41]. Briefly, a small excess of NN ligand (1,10-phenanthroline (phen), 4,7-diphenyl-1,10-phenanthroline (ph2phen), pyrazino[2,3-f]-1,10-phenanthroline (dpq)) and [ClRe(CO)5] were mixed in xylene (Synth) and heated to reflux for 6h. The hot mixture was separated by filtration. Then the correspondent fac-[ReCl(CO)3(NN)] was suspended to a 30mL argon saturated dichloromethane, and after one hour, a 10-fold excess of trifluoromethanesulfonic acid (tfms) was added. The solution was stirred for one hour, and the resulting product, fac-[Re(tfms)(CO)3(NN)], was obtained by slow addition of ethyl ether. Lastly, in a 30mL of argon saturated solution of fac-[Re(tfms)(CO)3(NN)] complex was added to a small excess of 4-(phenylseleno)-pyridine (PhSepy) and heated to reflux under an argon atmosphere for 6h. After cooling to room temperature, the final product was precipitated by the addition of solid NH4PF6. The yellow solid was separated by filtration, washed with water and ethyl ether. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | In ethanol excess acid in EtOH added to soln. of Cu-compound; addn. of dpphen in EtOH;; filtration; leaving overnight; crystn.; filtration; washing (EtOH); drying (vacuum); elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | In water; ethylene glycol other Radiation; Ir complex and ligand suspended in ethylene glycol, under purging N2 atm. suspn. subjected to reflux for 15 min in microwawe oven with frequencyof 2450 MHz, cooled to room temp., pptd. with satd. aq. soln. of KPF6; filtered, recrystd. from MeCN/Et2O; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41.91% | Stage #1: 2-(4-bromophenyl)benzothiazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: bathophenanthroline In tetrahydrofuran; hexane at -78 - 20℃; | 1 Synthesis of 2-(4-(benzo[d]thiazol-2-yl)phenyl)-4,7-diphenyl-1,10-phenanthrolineTo a three-necked flask of 250 ml, 1.63 g (5.6 mmol) of 2-(4-bromophenyl)benzo[d]thiazole and 70 ml of THF were charged, then 3.5 ml (5.6 mmol) n-butyllithium (1.6M in Hexane solution) was dropped under stirring at -78° C. in a nitrogen atmosphere. The mixture was stirred for one hour at -78° C., and a solution of 1.86 g (5.6 mmol) 4,7-diphenyl-1,10-phenanthroline in 30 ml THF was dropped. Then the mixture was stirred at room temperature for overnight and was added with water. The organic layer was extracted with Dichloromethane and dried with anhydrous magnesium sulfate, the solvent was removed by rotary evaporation. The product was purified by column chromatography on alumina using Dichloromethane/Hexane as eluent and dried in vacuo, obtaining white powder compound 1.27 g (yield of 41.91%), MS (m/z, FAB+) 541.6. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52.14% | Synthesis of 2,9-bis(4-(benzo[d]oxazol-2-yl)phenyl)-4,7-diphenyl-1,10-phenanthrolineTo a three-necked flask of 250 ml, 6.03 g (22 mmol) of <strong>[3164-13-4]2-(4-bromophenyl)benzo[d]oxazole</strong> and 70 ml of THF were charged, then 13.8 ml (22 mmol) n-butyllithium (1.6M in Hexane solution) was dropped under stirring at -78 C. in a nitrogen atmosphere. The mixture was stirred for one hour at -78 C., and a solution of 1.86 g (5.6 mmol) of 4,7-diphenyl-1,10-phenanthroline in 30 ml THF was dropped. Then the mixture was stirred at room temperature for overnight and was added with water. The organic layer was extracted with Dichloromathane and dried with anhydrous magnesium sulfate, the solvent was removed by rotary evaporation. The product was purified by column chromatography on alumina using Dichloromethane/Hexane as eluent and dried in vacuo, obtaining white powder compound 2.10 g (yield of 52.14%). MS (m/z, FAB+) 718.8. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54.56% | Stage #1: 2-bromonaphthalene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: bathophenanthroline In tetrahydrofuran; hexane at -78 - 20℃; | 6 EXAMPLE 6Synthesis of Comparable Example 2Synthesis of 2,9-di(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthrolineTo a three-necked flask of 250 ml, 4.56 g (22 mmol) of 2-bromonaphthalene and 70 ml of THF were charged, then 13.8 ml (22 mmol) n-butyllithium (1.6M in Hexane solution) was dropped under stirring at -78° C. in a nitrogen atmosphere. The mixture was stirred for one hour at -78° C., and a solution of 1.86 g (5.6 mmol) 4,7-diphenyl-1,10-phenanthroline in 30 ml THF was dropped. Then the mixture was stirred at room temperature for overnight and was added with water. The organic layer was extracted with Dichloromethane and dried with anhydrous magnesium sulfate, the solvent was removed by rotary evaporation. The product was purified by column chromatography on alumina using Dichloromethane/Hexane as eluent and dried in vacuo, obtaining white powder compound 1.79 g (yield of 54.56%). MS (m/z, FAB+) 584.7. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | To a three-necked flask of 300 ml, 5.8 g (18.1 mmol) of <strong>[144981-85-1]2-iodo-9,9-dimethylfluorene</strong> [1] and 80 ml of diethyl ether were charged and 11.7 ml (18.1 mmol) of n-butyllithium (hexane solution of [15percent)] was dropped under stirring at-78°C in a nitrogen atmosphere. The mixture was raised to room temperature and stirred for one hour, and then cooled to-20°C and a dispersion of 1.5 g (4.51 mmol) of bathophenanthroline [2] in 100 ml of toluene was dropped. The mixture was stirred at room temperature for 12 hours and was added with water. The organic layer was extracted with chloroform and dried with anhydrous sodium sulfate, and then purified with an alumina column (hexane/chloroform solvent mixture developer), obtaining 2.4 g (yield of [74percent)] of Exemplary Compound No. 2 (yellow crystal). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; water elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | In ethanol; water at 20℃; | 2.3 Synthesis of [Cu(qui)(bpy)]BF4·H2O (1), [Cu(qui)(phen)]BF4 (2), [Cu(qui)(ambpy)]BF4 (3), [Cu(qui)(mphen)]BF4·H2O (4), [Cu(qui)(nphen)]BF4 (5) and [Cu(qui)(bphen)]BF4 (6) General procedure: To a solution of 2-phenyl-3-hydroxy-4(1H)-quinolinone (237 mg, 1 mmol) in ethanol (50 mL), the corresponding bidentate N-donor ligand (L) (1 mmol) dispersed in EtOH (5 mL) was added while stirring. To this mixture, a solution of Cu(BF4)2·H2O (237 mg, 1 mmol) in H2O (5 mL) was slowly added while stirring. The reaction mixture was stirred at room temperature for a few hours, and subsequently left to stand for several days at room temperature. The obtained solid product was filtered off, washed with a small amount of cold water and ethanol, and dried in the air at 40 °C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In 1,2-dimethoxyethane for 72h; Inert atmosphere; Reflux; | Synthesis of tris(4,7-diphenyl-1,10-phenanthroline)ruthenium(II) chloride (I) The [Ru(dpphen)3]Cl2 is synthesized using literature method [35] . RuCl3⋅3H2O (1 mmol) and 4,7-diphen-1,10-phenanthroline (3 mmol) is taken in ethylene glycol under nitrogen atmosphere and heated to reflux for 72 h and the crude product is chromatographed using silica gel. The solution on evaporation yielded orange red crystals. Yield = 85% ESI-MS (m/z) 548.6496 (M-2Cl- doubly charged species). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; In ethanol; water; | General procedure: In the preparation of the Ln(CA)3·Phn and Ln(CA)3·Bpy adducts the 3-N NaOH water solution and an ethanol solution of Phn or Bpy were added to an ethanol solution of CA. Then, a water?ethanol (1:1) solution of LnCl3·6H2O was drop by drop added to the previous mixture at heating in a water bath (at 60?70°C) or sometimes without heating. A molar ratio of the reagents CA: Phn (Bpy): lanthanide chloride: NaOH was equal to 3:1:1:3. The compound Eu(AcCHex)3·Phen was also synthesized by other method involving the preparation of an ethanol solution of a mixture of CA, Phen and EuCl3·6H2O in a molar ratio of 3:1:1 and adjusting the pH value of reaction mixture to 6 with a liquid ammonia. It should be pointed out that the heating of the reaction mixture results in a decrease in the keto/enol ratio of cycloalkanone [37] that promotes a binding of CA with the Ln3+ ion. At the same time, the probability of decomposition of cycloalkanonate anion increases. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | Stage #1: 1-bromo-4-(trimethylsilyl)benzene With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 2h; Inert atmosphere; Stage #2: bathophenanthroline In tetrahydrofuran; hexane for 24h; Reflux; Inert atmosphere; | 2 2.2.1. Synthesis of 4,7-diphenyl-2-(4-(trimethylsilyl)phenyl)-1,10-phenanthro-line (Bath-1) General procedure: BrPhSiMe3 (0.824 g, 3.6 mmol) was dissolved in 80 mL freshly distilled THF in a 200 mL flask under N2 at 78°C, then n-butyllithium (2.5 mL, 4.0 mmol, 1.6 M in hexane) was added dropwise in 1 h and stirred 1 h at room temperature. Bath (0.720 g,3.6 mmol) was added into the mixture which was then refluxed for 24 h and then quenched with water. The resulting mixture was extracted with CH2Cl2. The organic layer was stirred with the activated MnO2 (1.910 g) for 12 h and then dried over MgSO4. After removing the solvent, the residue was purified by column chromatography on silica gel using ethyl acetate/petroleum ether (v/v 1/3) as the eluent, which was then recrystallized from n-hexane and diethyl ether (v/v 1/1) to give a yellow solid. Yield: 0.829 g,48.0%. 1H NMR (CDCl3, 400 MHz, ppm): 9.718 (s, 1H), 8.714 (s, 2H),8.223 (s, 1H), 8.017 (s, 1H), 7.909 (d, 2H), 7.786 (d, 2H), 7.593 (m,10H), 0.331 (s, 9H). 13C NMR (CDCl3, 400 MHz, ppm): 157.04, 149.76,149.07, 148.36, 146.95, 146.80, 144.71, 140.01, 138.29, 138.01, 133.71,129.61, 128.56, 128.51, 128.38, 127.16, 126.72, 125.39, 123.86, 123.62,123.25, 121.17, 1.17. FT-IR (KBr, cm1): 3060, 2957, 2858, 1727,1540, 1249, 835, 702. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48.4% | BrPhSiMe3 (0.824 g, 3.6 mmol) was dissolved in 80 mL freshly distilled THF in a 200 mL flask under N2 at 78C, then n-butyllithium (2.5 mL, 4.0 mmol, 1.6 M in hexane) was added dropwise in 1 h and stirred 1 h at room temperature. Bath (0.720 g,3.6 mmol) was added into the mixture which was then refluxed for 24 h and then quenched with water. The resulting mixture was extracted with CH2Cl2. The organic layer was stirred with the activated MnO2 (1.910 g) for 12 h and then dried over MgSO4. After removing the solvent, the residue was purified by column chromatography on silica gel using ethyl acetate/petroleum ether (v/v 1/3) as the eluent, which was then recrystallized from n-hexane and diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With sodium hydroxide; In ethanol; at 20℃;pH 6 - 7; | General procedure: The synthetic route of binary and ternary europium complexes C1-C5 is demonstrated in Scheme 2. A solution of EFBA (3 mmol) in ethanol was added dropwise to the aqueous solution of europium nitrate (1 mmol) with constant stirring on magnetic stirrer at room temperature. pH of the resulting mixture was set between 6-7 by using dilute NaOH (0.05 M) and white color precipitates were obtained. The resulting precipitates were vaccum filtered along with washing of water and ethanol to remove the unreacted ligand and then dried in vaccum desiccator to obtain the white powder of Eu(EFBA)3(H2O)2 (C1) complex. Complexes C2-C5 were prepared by the same procedure as adopted for the synthesis of complex C1 but in addition to the reaction mixture of EFBA (3 mmol) and europium nitrate (1 mmol) there is extra addition of ethanolic solution of neo (1 mmol), batho (1 mmol), phen (1 mmol), and bipy (1 mmol) for the synthesis of ternary europium complexes C2-C5, respectively. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; dichloromethane at 20℃; for 0.5h; | Preparation of the CT products General procedure: A simple synthetic protocol that was used for the preparation of CTcomplexes of Bath donor is briefly described as follows. First, 2 mmolof Bath donor in a 1:1 MeOH/CH2Cl2 mixture (20 mL) was added to 20 mL of a solution containing 2 mmol of the acceptor (either PA,DNBA or CLA) in the same solvent mixture. The resulting mixture wasstirred at room temperature for approximately 0.5 h, where theresulting precipitation were isolated as shiny yellow, pale yellow, andviolet crystals for Bath-PA, Bath-DNBA, and Bath-CLA products, respectively.The formed products were isolated, filtered, and further purifiedusing solventmixture and a recrystallization process to obtain the pureproducts. The products were then collected and dried in vacuo for 48 h.The products were characterized by spectroscopy (UV-Vis, IR, 1H NMR,and 13C NMR) as well as elemental analysis. The excellent agreementbetween the experimental and calculated values of C, H, and N indicatesthat the obtained productswere free of impurities. The stoichiometry ofthe Bath interaction with the acceptors was found to have a 1:1 ratio. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | In methanol; dichloromethane; at 20℃; for 5h; | Follow a similar procedure as 2, <strong>[6737-42-4]dppp</strong> (0.2mmol, 0.0825g) and Bphen (0.2mmol, 0.0665g) were added into the stirring solution of AgClO4 (0.2mmol, 0.0415g) in a mixture of CH2Cl2 (5ml) and CH3OH (5ml) for 5h at ambient temperature. The insoluble residues were removed by filtration, and the brown filtrate was evaporated slowly at room temperature for about one week to yield white crystals. Yields: 77%. Anal. Calc. for C102H84Ag2Cl2N4O8P4: elemental analysis: C, 64.32; H, 4.41; N, 2.94%. Measured value: C, 64.76; H, 4.52; N, 2.91%. IR (cm-1, KBr pellets): 3435m, 3051m, 2928w, 1965w, 1619m, 1588m, 1560s, 1517s, 1491s, 1434vs, 1424s, 1384s, 1308m, 1270w, 1233m, 1182m, 1097vs, 1026m, 999m, 954m, 854s, 829s, 767vs, 737vs, 701vs, 623vs, 593m, 574m, 547m, 509s, 479s, 441m. 1H NMR (600MHz, CDCl3, 298K): delta=1.5 (br, 4H, <strong>[6737-42-4]dppp</strong>-CH2CH2CH2), 2.7 (br, 8H, <strong>[6737-42-4]dppp</strong>-CH2CH2CH2), 7.0-7.6 (m, with solvent signal peak overlap, <strong>[6737-42-4]dppp</strong>-ph, Bphen-ph), 7.7 (br, 4H, H5,6-Bphen), 8.9 (br, 4H, H2,9-Bphen)ppm. 31P NMR (243MHz, CDCl3): delta=4.79 (d, JAg-P=430Hz), -5.93 (d, JAg-P=233Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65.5% | General procedure: The amino acid (1.0 mmol) and KOH (0.06 g, 1.0 mmol) were dissolved in 15 mL of hot methanol?water (v/v, 1 : 1) with stirring and added successively to a methanol solution (5 mL) of aldehyde (1.0 mmol). The mixture was then stirred at 75°C for 2 h. Subsequently, a solution of vanadyl sulfate (0.16 g, 1.0 mmol) in water (5 mL) was added dropwise and stirred at 75°C for 2 h. A solution of 1,10-bathophenanthroline (0.20 g, 1.0 mmol) in 5 mL of methanol was then added dropwise and the mixture stirred for 1 h. Finally, the resulting solution was filtered and gave a brick-red precipitate. The solid was washed with MeOH and diethyl ether, and finally dried under vacuum over P4O10. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | In dichloromethane for 6h; | 2.2.1 Synthesis of [Cu(dppbe)(Bphen)](ClO4)·2CH3OH}n (1) A mixture of [Cu(CH3CN)4](ClO4) (0.0654g, 0.2mmol), dppbe (0.0893g, 0.2mmol) and Bphen (0.0665g, 0.2mmol) were dissolved in a mixture of CH2Cl2 (5ml) and CH3OH (5ml), then stirred for 6h. The insoluble residues were removed by filtration and the filtrate was evaporated slowly at room temperature for a week to yield a yellow crystalline product. Yield: 74%. Anal. Calc. for C56H48ClCuN2O6P2: C, 66.81; H, 4.77; N, 2.78. Found: C, 67.71; H, 4.75; N, 2.86%. IR (cm-1): 3446s, 2377w, 2345w, 1622m, 1553w, 1515w, 1481w, 1436m, 1121s, 1091vs, 866w, 742m, 697s, 668w, 623m, 531m, 496w. 1H NMR (600MHz, CDCl3, 298K) δ, ppm: 7.2-7.8 (m, overlap with the solvent peak signal, Bphen-aromatic ring, dppbe-aromatic ring), 8.8 (d, Bphen-aromatic ring). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | In tetrahydrofuran at 20℃; for 0.75h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With triethylamine In 1,4-dioxane; methanol at 20℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In methanol; dichloromethane; at 20℃; for 6h; | A mixture of CuBr (28.7mg, 0.2mmol) and <strong>[6737-42-4]dppp</strong> (82.5mg, 0.2mmol) with an excess of batho (66.5mg, 0.2mmol) were dissolved in CH2Cl2 (5mL) and CH3OH (5mL) solution, stirred at room temperature for 6h. The insoluble residues were removed by filtration, and the filtrate was evaporated slowly at room temperature to yield yellow crystalline products. Yield: 80%. Anal. Calc. for C53H50BrCuN2O2P2: C, 66.84; H, 5.29; N, 2.94. Found: C, 66.97; H, 5.15; N, 2.88%. IR (KBr disc, cm-1): 3378s, 3048w, 2858w, 2580w, 1616w, 1556m, 1515m, 1433s, 1414m, 1229m, 1026s, 998w, 767m, 740s, 698vs, 513s, 482m. 1H NMR (600MHz, CDCl3, 298K): delta 7.87-8.98 (d, 6H, batho CH), 7.56-7.68 (m, 10H, batho CH), 7.41-7.24 (m, 20H, <strong>[6737-42-4]dppp</strong> CH), 2.91-2.81 (m, 4H, CH2), 2.78-2.63 (m, 2H, CH2); 31P NMR (400MHz, CDCl3, 298K): -12.25, -14.84. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | In methanol; dichloromethane; at 20℃; for 6h; | General procedure: A mixture of CuCl (19.6mg, 0.2mmol) and dppb (89.3mg, 0.2mmol) with an excess of batho (66.5mg, 0.2mmol) were dissolved in CH2Cl2 (5mL) and 17 CH3OH (5mL) solution, stirred at room temperature for 6h. The insoluble residues were removed by filtration, and the filtrate was evaporated slowly at room temperature to yield yellow crystalline products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In methanol; dichloromethane; at 20℃; for 6h; | General procedure: A mixture of CuBr (28.7mg, 0.2mmol) and <strong>[6737-42-4]dppp</strong> (82.5mg, 0.2mmol) with an excess of batho (66.5mg, 0.2mmol) were dissolved in CH2Cl2 (5mL) and CH3OH (5mL) solution, stirred at room temperature for 6h. The insoluble residues were removed by filtration, and the filtrate was evaporated slowly at room temperature to yield yellow crystalline products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | In methanol; dichloromethane at 20℃; for 6h; | 6 2.2.6 [Cu(dppb)(batho)]Cl (6) General procedure: A mixture of CuCl (19.6mg, 0.2mmol) and dppb (89.3mg, 0.2mmol) with an excess of batho (66.5mg, 0.2mmol) were dissolved in CH2Cl2 (5mL) and 17 CH3OH (5mL) solution, stirred at room temperature for 6h. The insoluble residues were removed by filtration, and the filtrate was evaporated slowly at room temperature to yield yellow crystalline products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | In methanol; dichloromethane; at 20℃; for 6h; | General procedure: A mixture of CuCl (19.6mg, 0.2mmol) and dppb (89.3mg, 0.2mmol) with an excess of batho (66.5mg, 0.2mmol) were dissolved in CH2Cl2 (5mL) and 17 CH3OH (5mL) solution, stirred at room temperature for 6h. The insoluble residues were removed by filtration, and the filtrate was evaporated slowly at room temperature to yield yellow crystalline products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In methanol; dichloromethane at 20℃; for 6h; | 6 2.2.6 [Cu(dppb)(batho)]Cl (6) A mixture of CuCl (19.6mg, 0.2mmol) and dppb (89.3mg, 0.2mmol) with an excess of batho (66.5mg, 0.2mmol) were dissolved in CH2Cl2 (5mL) and 17 CH3OH (5mL) solution, stirred at room temperature for 6h. The insoluble residues were removed by filtration, and the filtrate was evaporated slowly at room temperature to yield yellow crystalline products. Yield: 80%. Anal. Calc. for C54H40ClCuN2P2: C, 73.83; H, 4.59; N, 3.19. Found: C, 73.62; H, 4.73; N, 3.06%. IR (KBr disc, cm-1): 3652m, 3279w, 3049w, 1962w, 1614m, 1555m, 1514w, 1481m, 1433w, 1410w, 1384w, 1226m, 1095s, 1025w, 865s, 836m, 769s, 745s, 696vs, 663w, 628w, 529s, 484s. 1H NMR (600MHz, CDCl3, 298K) δ 8.39ppm (d, 2H), 8.06ppm (d, 2H), 7.74ppm (d, 2H), 7.69ppm (m, 4H), 7.63ppm (m, 10H), 7.41-7.31ppm (m, 20H); 1P NMR (400MHz, CDCl3, 298K) δ -2.62ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | With sodium hydroxide In ethanol; water at 40 - 50℃; for 4h; | 2.2. Synthesis Stock 0.5M solution of EuCl3 was prepared by the treatment of Eu2O3(4.400 g, 12.50 mmol) by minimum amount of concentrated HCl in aquartz crucible. The resulting solution was evaporated to dryness at 90 °Cand the residue was dissolved in a minimum amount of distilled water.After that, the solution was transferred quantitatively to a volumetric flaskand the volume was adjusted to 50 mL. This solution was then kept in apolypropylene flask. To a stirred warm (40 °C) solution of the ligand(3 mmol) and (1 mmol) bathophenanthroline (0.33 g) in 30 mL of ethanol,2 mL of an 0.5M aqueous solution of EuCl3 (1 mmol) were added dropwise,followed by careful addition of 3 mL (3 mmol) of an 1.0M NaOHsolution in water until the pH of the mixture reached 6-7. The mixture washeated at 50 °C during 4 h in a closed flask and cooled. Further operationsdepended upon the properties of the reaction products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetone; for 0.5h; | General procedure: To the solution lanthanide chloride hexahydrate (0.05g, 0.12mmol) in acetone (10mL) the solution of Phen/BPhen (0.02/0.05, 0.12mmol) in acetone (10mL) was added. After prolonged stirring, the solution of 0.06g of <strong>[119130-94-8]potassium benzoxazole-2-carboxylate</strong> in 10mL of acetone was added to a mixture. Then mixture was stirred for 30min and the precipitate was filtered off. The filtrate was evaporated to dryness, redissolved in 30mL of water and evaporated on a rotary evaporator. Yield 0.05/0.05g (48/41%). Pale brown powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | In N,N-dimethyl-formamide at 120℃; for 36h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With sodium hydroxide In water at 50℃; for 3h; | 2.2. Preparation of Samarium(III) complexes General procedure: Solution of Sm(NO3)36H2O (0.2225 g in double-distilled water) wasadded in small lots to a stirred solution of ligand L (0.365 g in distilledethanol). After achieving constant pH of approx. 6.5-7 using aqueous0.05 N sodium hydroxide, this solution was kept under constant stirringat 50 C for 3 h. The obtained precipitates were filtered, washed with 10mL water and 10 mL ethanol, and then kept in a desiccator to attain adried product of binary complex C1. For synthesizing ternary Sm(III)complexes C2-C5, the ethanol solution of secondary ligand [phen(0.090 g, 1 mol), bipy (0.078 g, 1 mol), neo (0.104 g, 1 mol), bathophen(0.180 g, 1 mol)] was added to the already stirred solution of ligand Land the metal ion in a 3:1 M ratio through the same procedure as appliedfor complex C1. The prepared complexes were soluble in dimethylsulfoxide; hence, the UV-vis absorption and photoluminescence studiesof complexes were studied in this solvent [39]. The schematic preparatoryroute of Samarium(III) complexes is represented in Fig. 1 and theelectrospray mass spectra of complexes C1-C5 are shown in the supplementary information Fig. S1-S5. The calculation of mass wasdone by multiplying the charge on the complexes i.e 1+ by m/z valueobtained in the spectra. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With ammonium peroxydisulfate In water; dimethyl sulfoxide at 50℃; for 24h; Inert atmosphere; Sealed tube; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; for 36h;Reflux; Inert atmosphere; | General procedure: First, the product E2-2 is obtained from E2-1 through the Suzuki cross coupling reaction according to the above route, and then the product E2-2 is sequentially processed according to the above reaction scheme to obtain the product E2-4. E2-4 (6.46g, 17.60mmol), E1-1 (2.64g, 8.00mmol) were added to a 500mL round-bottomed flask, and a mixed system of toluene (150ml), ethanol (50mL) and deionized water (100mL) was used as Solvent, add Na2CO3 (6.12g, 57.78mmol) and Pd(PPh3)4 (1.08g, 0.933mmol) as catalyst, heat under reflux for 36 hours, filter after cooling, and successively use ethanol, dichloromethane/methanol mixed solution for many times The filter cake was washed and further processed by conventional methods to give the final product E-2 (3.22 g, 54% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | Re(CO)5Cl (0.5g, 1.382mmol)and metal ligand DIP (0.459 g, 1.382 mmol) was added to 60 mL of toluene,Under the protection of N2, stir at 110 C for 6 h,The reaction solution was spin-dried under reduced pressure to obtain Re(DIP)(CO)Cl,Again with silver triflate (0.355 g, 1.382 mmol) in 80 mL of acetonitrile,Under the protection of N2, stir at 85 C for 20 h,After cooling and filtration, AgCl was removed, and the filtrate was concentrated.Add saturated NH4PF6 aqueous solution and stir for 2h,The NH4PF6 in the saturated NH4PF6 aqueous solution is 6 times the molar amount of Re(CO)5Cl,Add 80 mL of water to separate out a yellow solid,After filtration, the solid was washed with water and ether, and dried under vacuum at 45C to obtain Re(DIP)(CO)3(CH3CN),Yield 81%; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61 % | Stage #1: tol-BINAP; copper(I) bromide In dichloromethane at 20℃; Inert atmosphere; Darkness; Stage #2: bathophenanthroline In dichloromethane Inert atmosphere; Darkness; Reflux; |
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