Water → Cobalt tetrakis(4-ethynylphenyl)porphyrin

HRID 2074043Notes

Reaction equation

HRID 2074043 reaction equation
O.O.O.O.C([O-])(=O)C.[Co+2:9].C([O-])(=O)C.C12C=C3N=C(C=C3)C=C3NC(C=C3)=CC3=NC(C=C3)=CC(N1)=CC=2.[C:38]([C:40]1[CH:45]=[CH:44][C:43]([C:46]2[C:65]3[NH:66][C:62](=[CH:63][CH:64]=3)[C:61]([C:67]3[CH:72]=[CH:71][C:70]([C:73]#[CH:74])=[CH:69][CH:68]=3)=[C:60]3[N:75]=[C:57]([CH:58]=[CH:59]3)[C:56]([C:76]3[CH:81]=[CH:80][C:79]([C:82]#[CH:83])=[CH:78][CH:77]=3)=[C:55]3[NH:84][C:52]([CH:53]=[CH:54]3)=[C:51]([C:85]3[CH:90]=[CH:89][C:88]([C:91]#[CH:92])=[CH:87][CH:86]=3)[C:50]3=[N:93][C:47]=2[CH:48]=[CH:49]3)=[CH:42][CH:41]=1)#[CH:39].O>CN(C=O)C>[C:82]([C:79]1[CH:78]=[CH:77][C:76]([C:56]2[C:55]3[NH:84][C:52](=[CH:53][CH:54]=3)[C:51]([C:85]3[CH:90]=[CH:89][C:88]([C:91]#[CH:92])=[CH:87][CH:86]=3)=[C:50]3[N:93]=[C:47]([CH:48]=[CH:49]3)[C:46]([C:43]3[CH:44]=[CH:45][C:40]([C:38]#[CH:39])=[CH:41][CH:42]=3)=[C:65]3[NH:66][C:62]([CH:63]=[CH:64]3)=[C:61]([C:67]3[CH:68]=[CH:69][C:70]([C:73]#[CH:74])=[CH:71][CH:72]=3)[C:60]3=[N:75][C:57]=2[CH:58]=[CH:59]3)=[CH:81][CH:80]=1)#[CH:83].[Co:9]

Participants

6

Reactant 4

HCID 962WaterHCID 61372Cobalt(II) acetate tetrahydrateHCID 1359992435,10,15,20-tetrakis(4-ethynylphenyl)-21H,23H-PorphineHCID 13770524121H,22H-Porphine

Product 1

HCID 137227861Cobalt tetrakis(4-ethynylphenyl)porphyrinYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 8.71 g (35 mmol) of cobalt acetate tetrahydrate (Co(CH3COO)2.4H2O) in 100 ml of DMF was added portionwise to a solution of 1.7 g (2.39 mmol) of porphyrin TEPP (2) as obtained above in step 2), in 500 ml of DMF. The mixture obtained was refluxed for 20 hours. The heating was stopped and 150 ml of water were added to the reaction medium. The mixture was subsequently extracted with ethanol (4×200 ml) and the organic phase was then evaporated. The residue was dissolved in 300 ml of ethanol, and the organic phase was washed with 3×200 ml of water and dried over sodium sulfate. The solvent was evaporated off and the cobalt tetrakis(4-ethynylphenyl)porphyrin (Co-TEPP) (4) (1.19 g; 1.55 mmol; yield: 65%) was obtained in the form of a powder that was purple/black in color, and red in solution in chloroform.

Workup

  1. customThe mixture obtained
  2. temperaturewas refluxed for 20 hours
  3. extractionThe mixture was subsequently extracted with ethanol (4×200 ml)
  4. customthe organic phase was then evaporated
  5. dissolutionThe residue was dissolved in 300 ml of ethanol
  6. washthe organic phase was washed with 3×200 ml of water
  7. dry with materialdried over sodium sulfate
  8. customThe solvent was evaporated off

Sources & evidence

ORD record
ord-e045ffce964f454db3b0de71a4b4c582
Source dataset
uspto-grants-2011_04
Patent number
US07919046B2

Reaction notes

Loading…