Pyrrole → meso-Tetra(4-carboxyphenyl)porphine

HRID 728756Notes

Reaction equation

HRID 728756 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)([OH:3])=[O:2].[NH:12]1[CH:16]=[CH:15][CH:14]=[CH:13]1>C(O)(=O)CC>[C:1]([C:4]1[CH:11]=[CH:10][C:7]([C:8]2[C:16]3[NH:12][C:13]([C:8]([C:7]4[CH:10]=[CH:11][C:4]([C:1]([OH:3])=[O:2])=[CH:5][CH:6]=4)=[C:13]4[N:12]=[C:16]([C:8]([C:7]5[CH:10]=[CH:11][C:4]([C:1]([OH:3])=[O:2])=[CH:5][CH:6]=5)=[C:13]5[NH:12][C:16](=[C:8]([C:7]6[CH:6]=[CH:5][C:4]([C:1]([OH:3])=[O:2])=[CH:11][CH:10]=6)[C:13]6[CH:14]=[CH:15][C:16]=2[N:12]=6)[CH:15]=[CH:14]5)[CH:15]=[CH:14]4)=[CH:14][CH:15]=3)=[CH:6][CH:5]=1)([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 8027PyrroleHCID 120884-Formylbenzoic acid

Product 1

HCID 86278368meso-Tetra(4-carboxyphenyl)porphineYield 17.5%

Reagents, catalysts & solvents 1

HCID 1032Propionic AcidSolvent

Procedure

In refluxed propionic acid, 30 g of 4-carboxybenzaldehyde was reacted with 13.4 g of pyrrole to obtain 6.9 g of 5,10,15,20-tetra(4-carboxyphenyl)porphine. In a mixed solvent of 200 ml ofdistilled water and 300 ml of methanol was dissolved 10 g of polyvinyl alcohol having a polymerization degree of 2,000 and a saponification degree of 100%, and 0.066 g of the so-synthesized 5,10,15,20-tetra(4-carboxyphenyl)porphine was added to the solution. The solution was dried in a Petri dish to obtain a film having a guest concentration of 10-2M and a thickness of 0.5 mm. The sample was cooled to the liquid helium temperature and irradiated with a laser beam having a wavelength of 645 nm and an intensity of 1 mW/cm2 for 30 seconds to form a PHB hole. Then, the temperature of the film was elevatedto a predetermined level, the film was again cooled to the liquid helium temperature, and the half width of the PHB hole was measured.

Sources & evidence

ORD record
ord-46d0e6842e05423aaae33b134f1549b8
Source dataset
uspto-grants-1991_09
Patent number
US05051337

Reaction notes

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