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, Appendix IV : Experimental Protocols Synthesis of compounds made in chapter
, 20 mmol)is dissolved in 100 mL of water, the solution is then heated at 70°C under argon a solution of 1.2g (30 mmol) of NaOH solubilized in 150 mL of water is then added drop-wise during 30 minutes under constant bubbling, Cu2(OH)3OAc « classical » Copper (II) acetate (3.992g
, Copper (II) acetate (3.992g, 20 mmol) is dissolved in a mixture of 90 mL water and 10 mL ethanol, the mixture is then heated for 72h at 60°C without stirring. The obtained blue/green crystals are filtered and washed with water and ethanol, Cu2(OH)3OAc « one pot, pp.5-10
, Sodium dodecylsulfate (3.908g, 14.6 mmol) is dissolved in a mixture of 90 mL water and 60 mL ethanol with 15 minutes of argon bubbling. Cu2(OH)3OAc (520 mg, 2 mmol) is then added to the solution. This dispersion is maintained under argon and thermostated at 30°C for 72h. The blue powder is then washed with water and ethanol and dried under vacuum
, Sodium dodecylsulfate (1.332g, 5 mmol) is dissolved in a mixture of 70 mL water and 30 mL ethanol. Copper (II) acetate (1.999g, 10 mmol) is then added to the solution. The mixture is then heated to 60°C for 72h. The blue crystals are washed with water and ethanol then dried under vacuum. Yield : 40% few days, Cu2(OH)3(DS) « one pot
, 20 mmol) was dissolved in 200 mL of distilled water. The obtained solution is then argon bubbled for 30 minutes and heated at 70°C. In this solution is then added drop-wise an NaOH solution (0.6g, 15mmol) in a mixture of 180 mL of water and 120 mL of ethanol during one hour while keeping the bubbling. After the addition, the heating, stirring and bubbling is maintained for 15 minutes. The round bottom flask is then allowed to cool for 15 minutes in the oil bath and with an additional 15 minutes in air, p.30
, 6 mmol) is dissolved in a mixture of 90 mL water and 60 mL ethanol and put under argon bubbling for 15 minutes. The Co2(OH)3.2(OAc)0.8 (491 mg, 2 mmol) is added to the mixture. After 30 minutes of ultrasonication, the mixture is thermostated at 40 °C for 72 hours in an argon atmosphere. The green powder is filtered and washed with water then ethanol, p.93
OH)3.35(4-NH2-BzAc)0.65 or ,
, At this stage, Co2(OH)3.2(OAc)0.8 (496 mg, 2 mmol) was added along with 40 mL of ethanol. The mixture was stirred under argon at room temperature for 48 h. The dark green powder was collected by filtration, washed with water and ethanol, and dried under vacuum, Aminobenzoic acid (4-NH 2-BzAc) (822 mg, 6 mmol) was dissolved in water (160 mL) and the pH was adjusted to 8 using NaOH (0.2 mol L-1 )
, , p.85
, OH), vol.3, issue.3
, hexanal (150 mg, 1.5 mmol) and 20 mL of absolute ethanol were introduced in a 30 mL sealed microwave vessel. The mixture was placed under microwave irradiation (30 W) for 10 min. The dark green powder was collected by filtration, washed with ethanol and dried under vacuum, mg, 0.5 mmol), p.153
, Fluo-C)?Cu P-Fluo-C (91 mg, 0.33 mmol) was dissolved in 12 mL of water by adding 0.2M NaOH until reaching pH=8.3. Then 12 mL of ethanol was added in the solution along with Cu2(OH)3(DS) (70 mg, 0.15 mmol). The suspension was stirred under argon during 70 h at room temperature. The light blue solid was then filtered, washed with water and ethanol then dried under vacuum
, Yield : 50% (P-Fluo-C)?Co P-Fluo-C (91 mg, 0.33 mmol) was dissolved in 12 mL of water by adding 0.2M NaOH until a pH=8.3 was reached. Then 12 mL of ethanol was added in the solution along with Co2(OH)3(DSo) (70 mg, 0.16 mmol). The suspension was stirred under argon during 24h at room temperature. The green-bluish solid was then filtered, washed with water and ethanol then dried under vacuum, Analysis calculated for Co2
, Found : Cu : 39.11; C : 17.32; H : 3.86; P : 3.94. Yield : 70% P2-Fluo-C8?Co P2-Fluo-C8 (181 mg, 0.30 mmol) was dissolved in 12 mL of water by adding 0.2M NaOH until a pH=8.3 was reached. Then 12 mL of ethanol was added in the solution along with Co2(OH)3(DSo) (70 mg, 0.16 mmol). The suspension was stirred under argon and refluxed for 1h30. The green solid was then filtered, washed with water and ethanol then dried under vacuum
, Yield : 90% P2-Fluo-C?Cu P2-Fluo-C (118 mg, 0.33 mmol) was dissolved in 12 mL of water by adding 0.2M NaOH until a pH=8.3 was reached. Then 12 mL of ethanol was added in the solution along with Cu2(OH)3(DS) (77 mg, 0.16 mmol). The suspension was stirred under argon and refluxed for 1 hour. The light blue solid was then filtered, washed with water and ethanol then dried under vacuum, p.80
, Then 12 mL of ethanol was added in the solution along with Co2(OH)3(DSo) (70 mg, 0.16 mmol). The suspension was stirred under argon and refluxed for 2 hours. The green solid was then filtered, washed with water and ethanol then dried under vacuum, P2-Fluo-C?Co P2-Fluo-C (118 mg, 0.33 mmol) was dissolved in 12 mL of water by adding 0.2M NaOH until a pH=8.3 was reached, p.70
Then 12 mL of ethanol was added in the solution along with Cu2(OH)3(DS) (77 mg, 0.16 mmol). The suspension was stirred under argon and refluxed for 15 minutes. The light blue solid was then filtered, washed with water and ethanol then dried under vacuum, mg, 0.66 mmol) was dissolved in 12mL of water by adding 0.2M NaOH until a pH=8.8 was reached, p.90 ,
, Then 12 mL of ethanol was added in the solution along with Cu2(OH)3(DS) (77 mg, 0.16 mmol). The suspension was stirred under argon and refluxed for 15 minutes. The light blue solid was then filtered, washed with water and ethanol then dried under vacuum, P2-Fluo-H?Cu P2-Fluo-H (215 mg, 0.66 mmol) was dissolved in 12 mL of water by adding 0.2M NaOH until a pH=8.8 was reached, p.90
, mmol) was dissolved in 12 mL of water by adding NaOH until a pH=8.5 was reached. Then 12 mL of ethanol was added in the solution along with
, The suspension was stirred under argon and refluxed for 2h30. The green solid was then filtered, washed with water and ethanol then dried under vacuum
2 mg, 0.33 mmol) was dissolved in 12 mL of water by adding NaOH until reaching pH=8.8. Then 12 mL of ethanol was added in the solution along with Cu2(OH)3(DS) (76 mg, 0.16 mmol). The suspension was stirred under argon during 3 h at 70°C. The light grayish-blue powder was then filtered, vol.64 ,
33 mmol) was dissolved in 12 mL of water by adding NaOH until reaching pH=8.8. Then 12 mL of ethanol was added in the solution along with Cu2(OH)3(DS) (76 mg, 0.16 mmol). The suspension was stirred under argon during 3 h at 70°C. The light grayish-blue powder was then filtered, washed with water and ethanol then dried under vacuum. Analysis calculated for Cu2(OH)3.63(C6H5ClO3P)0, p.80 ,
33 mmol) was dissolved in 12 mL of water by adding NaOH until reaching pH=8.8. Then 12 mL of ethanol was added in the solution along with Cu2(OH)3(DS) (76 mg, 0.16 mmol). The suspension was stirred under argon during 3 h at 70°C. The light grayish-blue powder was then filtered, washed with water and ethanol then dried under vacuum, p.96 ,
Then 12 mL of ethanol was added in the solution along with Cu2(OH)3(DS) (76 mg, 0.16 mmol). The suspension was stirred under argon during 3 h at 70°C. The light grayish-blue powder was then filtered, washed with water and ethanol then dried under vacuum, vol.77 ,
,
Then 12 mL of ethanol was added in the solution along with Cu2(OH)3(DS) (76 mg, 0.16 mmol). The suspension was stirred under argon during 1h30 at 90°C. The light grayish-blue powder was then filtered, washed with water and ethanol then dried under vacuum, mmol) was dissolved in 12 mL of water by adding NaOH until reaching pH=8.6, p.96 ,
33 mmol) was dissolved in 12 mL of water by adding NaOH until reaching pH=8.8. Then 12 mL of ethanol was added in the solution along with Cu2(OH)3(DS) (76 mg, 0.16 mmol). The suspension was stirred under argon during 3 h at 70°C. The green powder was then filtered, washed with water and ethanol then dried under vacuum, p.70 ,
3 mg, 0.33 mmol) was dissolved in 12 mL of water by adding NaOH until reaching pH=8.3. Then 12 mL of ethanol was added in the solution along with Co2(OH)3.5(DSo)0.5 (70 mg, 0.16 mmol). The suspension was stirred under argon during 2 h at 90°C. The green powder was then filtered, washed with water and ethanol then dried under vacuum, vol.64 ,
Co : x; C : x; H : x; P : x, Cl : x. Yield : X%45.9mg ,
33 mmol) was dissolved in 12 mL of water by adding NaOH until reaching pH=8.6. Then 12 mL of ethanol was added in the solution along with Co2(OH)3.5(DSo)0.5 (70 mg, 0.16 mmol). The suspension was stirred under argon during 1 h at 90°C. The green powder was then filtered, washed with water and ethanol then dried under vacuum ,
27 mmol) was dissolved in 12 mL of water by adding NaOH until reaching pH=8.6. Then 12 mL of ethanol was added in the solution along with Co2(OH)3.5(DSo)0.5 (70 mg, 0.16 mmol). The suspension was stirred under argon during 1 h at 90°C. The green powder was then filtered, washed with water and ethanol then dried under vacuum, I?Co P-Bz-I (77.2 mg, 0 ,
,
Then 12 mL of ethanol was added in the solution along with Co2(OH)3.5(DSo)0.5 (70 mg, 0.16 mmol). The suspension was stirred under argon during 4h at 90°C. The green powder was then filtered, washed with water and ethanol then dried under vacuum, mmol) was dissolved in 12 mL of water by adding NaOH until reaching pH=8.6 ,
, Then 12 mL of ethanol was added in the solution along with Cu2(OH)3(DS) (76 mg, 0.16 mmol). The suspension was stirred under argon during 6h at 90°C. The grayish-blue powder was then filtered, washed with water and ethanol then dried under vacuum
, Yield : Close to 100% P2-diThio?Co P2-diThio (54.7 mg, 0.168 mmol) was dissolved in 20 mL of water by adding NaOH until reaching pH=8.7. Then 12 mL of ethanol was added in the solution along with Co2(OH)3.5(DSo)0.5 (69 mg, 0.16 mmol). The suspension was stirred under argon during 3h15 at 90°C. The green powder was then filtered, washed with water and ethanol then dried under vacuum, Yield : 88% P2-diThio?Cu P2-diThio (55.9 mg, 0.17 mmol) was dissolved in 12 mL of water by adding NaOH until reaching pH=8.8. Then 12 mL of ethanol was added in the solution along with Cu2(OH)3(DS) (76 mg, 0.16 mmol), vol.87
Yield : % P2-Thio?Co P2-Thio (41.5 mg, 0.170 mmol) was dissolved in 12 mL of water by adding NaOH until reaching pH=8.3. Then 12 mL of ethanol was added in the solution along with Co2(OH)4-x(Oleyl)x (19.2 mg, X mmol). The suspension was stirred under argon during 1h at 90°C. The green powder was then filtered, washed with water and ethanol then dried under vacuum, Oleyl?Cu Sodium oleyl sulfate (122 mg, 0.33 mmol) was dissolved in 15 mL of water.Then 10 mL of ethanol was added in the solution along with Cu2(OH)3(OAc) (40.8 mg, 0.16 mmol) ,
Cl2 (5) : A solution of (4) (0.13 g, 0.29 mmol) and cis[Ru(bpy)2Cl2]·2H2O (0.1g, 0.18 mmol) is mixed in a 40 mL DMF solution then refluxed under inert atmosphere and covered from light during 5 hours. The reactive medium is then evaporated and the solid is purified via column chromatography on sephadex LH20. The choice of methanol as eluant allows to obtain the desired product in the form of an orange powder ,
, Salicylaldehyde (17.5 mL, 164 mmol) and aniline (14.9 mL, p.164
, Anal. for A : C13H11NO (M = 197.08 g / mol) : Found (Calc.) (%) : C
, , vol.53
, IR (KBr pellet, cm-1 ) : 3055 w, N, 7.03 (7.10). 1 H NMR (CDCl3) : 8.62 (s, 1H), 7.43 (m, 4H), 7.31 (m, 3H), 7.05 (d, 1H), 6.96 (m, 1H), 1482.
, s, 1073 m, 1026 m, 979 m, 895 m, 822 m, 755 s, 687 m, 547 m, 519 m, vol.492, 1149.
, The mixture was heated and stirred for 2 hours at 100°C with a condenser. The red-brown solution was allowed to cool to room temperature. Then, the solution was poured onto ice (300 g) and a yellow lumbering solid formed. The solid was filtered and recrystallized in hot water. After cooling, a yellow powder was filtered, A (15.5 g, 56 mmol) was added to concentrated sulfuric acid (95%) (43 mL), pp.50-55
, Anal. for B·2H2O : C13H11NO4S·2H2O (M = 313.04 g / mol) : Found (Calc.) (%) : C, 50.43, vol.84, p.49
, IR (KBr pellet, cm-1 ) : 3395 m, 1 H NMR (DMSO-d6) : 10.24 (s, 1H), 9.07 (s, 1H), 8.02 (s, 1H), 7.65 (m, 1H), 7.45 (m, 4H), 7.35 (m, 1H), 6.95 (d ,1H)
, Anal. for C·1.5H2O : C7H5SO5Na·1.5H2O (M = 251.19 g / mol) : Found (Calc.) (%) : C, 33.53, vol.47, p.33
IR (KBr pellet, cm-1 ) : 3526 s, 3425 s, 3389 s, 3097 w, 3058 w, 2897 m, 1654 s, 1576 m, 1468 s, 1423 vw, s, 1H), 7.88 (d, 1H), 7.69 (d*d, 1H), 6.91 (d,1H ,
, Upon complete dissolution of C, the 4,5dimethylbenzene-1,2-diamine (0.61 g, 4.42 mmol) in 20 mL of methanol is slowly added to the solution of C. After addition, the mixture is then refluxed for two hours with an inclined condenser to get rid of water content. The bright yellow precipitate is filtered and is the desired salen compound, p.33
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