Réaction #2161225

ord-e045ffce964f454db3b0de71a4b4c582

Équation de réaction

O
water
CC(=O)[O-].CC(=O)[O-].O.O.O.O.[Co+2]
cobalt acetate tetrahydrate
C1=Cc2cc3ccc(cc4nc(cc5ccc(cc1n2)[nH]5)C=C4)[nH]3
porphyrin
C#Cc1ccc(-c2c3nc(c(-c4ccc(C#C)cc4)c4ccc([nH]4)c(-c4ccc(C#C)cc4)c4nc(c(-c5ccc(C#C)cc5)c5ccc2[nH]5)C=C4)C=C3)cc1
( 2 )
C#Cc1ccc(-c2c3nc(c(-c4ccc(C#C)cc4)c4ccc([nH]4)c(-c4ccc(C#C)cc4)c4nc(c(-c5ccc(C#C)cc5)c5ccc2[nH]5)C=C4)C=C3)cc1
tetrakis(4-ethynylphenyl)porphyrin
C#Cc1ccc(-c2c3nc(c(-c4ccc(C#C)cc4)c4ccc([nH]4)c(-c4ccc(C#C)cc4)c4nc(c(-c5ccc(C#C)cc5)c5ccc2[nH]5)C=C4)C=C3)cc1.[Co]
cobalt tetrakis(4-ethynylphenyl)porphyrin
Rendement 65.0%

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    AutreThe mixture obtained
  2. 2
    Températurewas refluxed for 20 hours
  3. 3
    ExtractionThe mixture was subsequently extracted with ethanol (4×200 ml)
  4. 4
    Autrethe organic phase was then evaporated
  5. 5
    workup.DISSOLUTIONThe residue was dissolved in 300 ml of ethanol
  6. 6
    Lavagethe organic phase was washed with 3×200 ml of water
  7. 7
    Séchagedried over sodium sulfate
  8. 8
    AutreThe solvent was evaporated off

Mode opératoire

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07919046B2uspto-grants-2011_04