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CAS No. : | 194861-72-8 | MDL No. : | MFCD30534199 |
Formula : | C24H16N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SAAQRUMAXVBWDL-UHFFFAOYSA-N |
M.W : | 332.40 | Pubchem ID : | 15320285 |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
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 |
---|---|---|
51% | With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,4-dioxane at 100℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 20% 2: 50% | layering of MeOH soln. of salt on benzene soln. of ligand, allowed to stand for 2 days; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | In methanol layering of MeOH soln. of salt on benzene soln. of ligand, allowed to stand for 2 days; filtration; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | In methanol layering of MeOH soln. of salt on nitrobenzene soln. of ligand, allowed to stand for 2 days; filtration; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In methanol; benzene layering of MeOH soln. of salt on benzene soln. of ligand, allowed to stand for 2 days; filtration; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | In methanol layering of MeOH soln. of salt on cyanobenzene soln. of ligand, allowed to stand for 2 days; filtration; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In methanol layering of MeOH soln. of salt on nitrobenzene soln. of ligand, allowed to stand for 2 days; filtration; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | In toluene for 48h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In toluene for 48h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In toluene for 48h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50.5% | In N,N-dimethyl-formamide at 95℃; for 72h; Sealed tube; High pressure; | 2.3.3. Preparation of [Cd2(L)3(2,6-ndc)2] (3) The preparation of complex 3was similar to that of 1, except thatCd(NO3)24H2O (31 mg, 0.1 mmol) was used instead ofZn(NO3)26H2O (30 mg, 0.1 mmol), and heated at 95 C for 3 days.Resulting in the formation of yellow particles and crystals of 3 wereobtained. Yield: 50.5% based on L. Anal Calcd (%) for C48H30N3O4Cd(%): C, 69.87; H, 3.66; N, 5.09. Found: C, 69.85; H, 3.68; N, 5.07. IR(KBrpellets, cm1): 3320(m), 3057(s), 2933(s), 1956(m), 1834(m),1654(s), 1603(s), 1564(s), 1491(s), 1400(s), 1359(s), 1219(s), 1192(s),1143(s), 1097(s), 1013(s), 931(s), 797(s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51.2% | In N,N-dimethyl-formamide at 70℃; for 120h; Sealed tube; High pressure; | 2.3.1. Preparation of [Zn3(L)(1,4-bdc)3]·2DMF (1) A mixture of Zn(NO3)26H2O (30 mg, 0.1 mmol), L (16.6 mg,0.05 mmol), 1,4-H2bdc (16.6 mg, 0.1 mmol) was put in a reactionvessel (10 ml) and DMF (3 ml) was added to it, then sealed, withultrasonic processing for 30 min the solid completely dissolved inDMF giving a clear solution. The reaction solution was heated at70 C for five days then cooled to room temperature and filtered,after the solid was washed with DMF and dried to obtain manyyellow petals crystals (ca. 51.2% yield based on L). Anal. Calcd (%) forC48H28N2O12Zn3 (%): C, 54.73; H, 3.53; N, 4.91. Found: C, 54.71; H,3.58; N, 4.89. IR (KBr pellets, cm1): 3062(m), 2926(s), 2856(s),1954(m), 1829(m), 1671(s), 1607(s), 1506(s), 1390(s), 1262(m),1134(s), 1096(s), 1023(m), 951(s), 885(s), 825(s), 750(s), 644(m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62.1% | In N,N-dimethyl-formamide at 95℃; for 96h; Sealed tube; High pressure; | 2.3.2. Preparation of [Zn2(L)(2,6-ndc)2]·3DMF (2) The preparation of complex 2was similar to that of 1, except that2,6-H2ndc (21.6 mg, 0.1 mmol) was used instead of 1,4-H2bdc(16.6 mg, 0.1 mmol), and heated at 95 C for four days. Resulting inthe formation of orange square crystals of 2 that were obtained.Yield: 62.1% based on L. Anal Calcd (%) for C117H105N11O23Zn4 (%): C,61.69; H, 4.36; N, 5.05. Found: C, 61.63; H, 4.37; N, 5.02. IR(KBrpellets, cm1): 3300(m), 3055(m), 2933(s), 1949(m), 1662(s),1608(s), 1514(m), 1457(m), 1418(s), 1358(s), 1259(s), 1217(s),1158(s),1091(s), 1068(s), 1030(s), 859(m), 824(s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; N,N-dimethyl-formamide for 12h; Inert atmosphere; | |
82% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; N,N-dimethyl-formamide at 100℃; for 24h; Inert atmosphere; | |
72% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 100℃; for 18h; Inert atmosphere; |
70% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In N,N-dimethyl-formamide; toluene at 130℃; for 48h; Inert atmosphere; | 2.2. Preparation of ligand L 9,10-dibromoanthracene (2.0 g, 5.95 mmol), Pyridine-4-boronicacid (2.4 g,17.8 mmol), K2CO3 (11.6 g, 35.5 mmol), Pd(PPh3)4 (0.68 g,0.59 mmol) and PhMe:DMF (6:1, 300 ml) were successively add to a500ml flask. Under N2 conditions, the reaction mixturewas heatedto 130 C in the dark for 48 h. After the reaction mixturewas cooledto room temperature and filtered to remove the catalyst by diatomaceousearth. The removal of solvent under reduced pressureyielded crude solid. The crude solid was dissolved in dichloromethaneand washed with distilled water, then dried over anhydrousmagnesium sulfate and concentrate dichloromethane underreduced pressure. A HCl solutionwas added and adjusted the pH to2e3. Solid precipitation was produced and then filtered, the solidwas dissolved in water and adjusted the pH to 8e9 by the additionof NaOH (10 M) solution. The pale yellow solid thus obtained byfiltration andwaswashed with distilledwater. Yield (1.4 g, 70%). MS(333.1387). 1H NMR (CDCl3-d6, dppm): 8.879 (m, 4H, pyridine-2),7.609 (m, 4H, anthracene-1), 7.456 (m, 4H, pyridine-3), 7.405 (t,4H, anthracene-2). |
70% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In N,N-dimethyl-formamide; toluene at 130℃; for 48h; Inert atmosphere; | |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 90℃; for 72h; Inert atmosphere; | ||
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; N,N-dimethyl-formamide at 100℃; for 18h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: Triisopropyl borate; n-butyllithium / tetrahydrofuran / 3 h / -78 °C 2: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide; water / 12 h / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With oxygen; 5,15,10,20-tetraphenylporphyrin In dichloromethane at -20℃; for 12h; Irradiation; | |
With oxygen In N,N-dimethyl-formamide UV-irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 92% 2: 39% | In toluene for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | at 85℃; for 72h; Sealed tube; | Synthesis of 1 (CCDC:1,534,561) A mixture of Cd(NO3)2·4H2O (31mg, 0.1mmol), dpa (16.6mg, 0.05mmol), and pta (16.6mg, 0.1mmol) in 3mL DMF was stirred in air for 30min and sealed in a 10mL Teflon lined stainless steel container. Then the reaction system was heated at 85°C for 3d. After cooling down to room temperature, yellow block crystals were obtained (yield: ca. 59% based on dpa). EA (%) Calcd for C32H20CdN2O4: C 63.11, H 3.32, N 4.60; found C 63.09, H 3.35, N, 4.57. FT-IR (cm-1, KBr): 3064s, 2922s, 2855s, 1953m, 1825m, 1676vs, 1604s, 1565vs, 1380s, 1294m, 1220vs, 951s, 885m, 828vs, 749vs, 677s, 642s, 613vs. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53.8% | at 100℃; for 72h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
600 mg | In dichloromethane at 5℃; for 0.666667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With hydrogen iodide In water at 145℃; for 168h; Autoclave; High pressure; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | In dichloromethane at 20℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | In dichloromethane at 20℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | at 20℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37% | In dichloromethane at 20℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | In dichloromethane at 20℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; dichloromethane Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; dichloromethane Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; dichloromethane Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With oxygen; methylene blue In d(4)-methanol Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | In methanol; dichloromethane at 50℃; for 10h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | In acetonitrile at 72℃; for 90h; | |
In ethanol at 90℃; for 120h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: ethanol / 120 h / 90 °C / Inert atmosphere 2: ethanol / 12 h / 90 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: ethanol / 120 h / 90 °C / Inert atmosphere 2: ethanol / 12 h / 90 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 100℃; for 72h; Autoclave; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N,N-dimethyl-formamide at 120℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88.4% | In water; acetone at 70℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane for 0.333333h; | 2.3 Preparation of 2 L2 (0.0332g, 0.1mmol) was added into 3mL dichloromethane (DCM). (NH4)2WS4 (0.0688g, 0.2mmol), CuI (0.0312g, 0.6mmol), NaI (0.090g, 0.6mmol) were added into 6mL DMF. The two solutions were stirred for 20min, and then the resulting DCM solution was filtered into a glass tube. 1.5mL DCM and 6mL DMF filtrate were slowly layered on the surface of the filtrate in turn. Two weeks later, red block crystals were obtained for 2. Anal. (%) Calcd. for C78H64Cu4I2N8O2S4W: C, 47.58; H, 3.19; N, 5.72. Found: C, 47.62; H, 3.28; N, 5.70. IR (KBr pellet, cm-1): 3428(s), 1602(s), 1413(s), 1067(s), 813(s), 770(s), 642(s), 548(s), 435(s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15% | at 20℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | With ammonium hydroxide In ethanol at 20℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With nitric acid In ethanol at 80℃; for 72h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With nitric acid In ethanol at 80℃; for 72h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With nitric acid In ethanol at 80℃; for 72h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | In water at 80℃; for 72h; Autoclave; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | In N,N-dimethyl-formamide at 80℃; for 72h; Autoclave; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In water; N,N-dimethyl-formamide at 80℃; for 72h; Autoclave; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water; acetone at 60℃; for 12h; | Results and Discussion Here, ANTHR-based metallacycle was synthesized using ANTHRbasedligands (9,10-di(pyridin-4-yl)anthracene [DPA]), dicarboxylatemoieties (isophthalic acid [IPA2-]), and cis-(PEt3)2Pt(OTf)2. Themetallacycle was readily prepared using a heteroligation-directedthree-component CDSA strategy. As shown in Scheme 1 A and B,metallacycle 1 was formed by the reaction of pyridyl-functionalizedANTHR ligand (2), dicarboxylate ligand (3), and phosphine-capped90° Pt(II) acceptor (4) at a molar ratio of 1:1:2. Compounds 2 and 3were dissolved in acetone and water, respectively. The two solutionswere then mixed, and 4 in acetone was added. After heating at60 °C for 12 h, the solvent was evaporated via N2 flow. The resultantproduct 1 was obtained after drying under vacuum (SI Appendix). |