Reacción #2161225

ord-e045ffce964f454db3b0de71a4b4c582

Ecuación de reacción

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
Rendimiento 65.0%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroThe mixture obtained
  2. 2
    Temperaturawas refluxed for 20 hours
  3. 3
    ExtracciónThe mixture was subsequently extracted with ethanol (4×200 ml)
  4. 4
    Otrothe organic phase was then evaporated
  5. 5
    workup.DISSOLUTIONThe residue was dissolved in 300 ml of ethanol
  6. 6
    Lavadothe organic phase was washed with 3×200 ml of water
  7. 7
    Secadodried over sodium sulfate
  8. 8
    OtroThe solvent was evaporated off

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07919046B2uspto-grants-2011_04