Water → Zinc(II) 5,10,15,20-Tetrakis[m-(S-acetylthiomethyl)phenyl]porphyrin

Participants

Reaction Steps

A mixture of 16.2 mg of 29 (16.7 μmol) in 20 mL of CHCl3 and a solution of 80.0 mg of Zn(OAc)2.2H2O (365 μmol) in 5 mL of methanol were combined and stirred at ambient temperature. After 2 h the metalation was completed (checked by fluorescence excitation spectroscopy) and 40 mL of H2O was added. The phases were separated and the organic layer was washed three times with 5% NaHCO3 and dried (Na2SO4). The solvents were removed under reduced pressure. Column chromatography over flash silica gel with CH2Cl2/hexanes (4:1) gave the title compound as a purple solid in quantitative yield. IR (neat): {tilde over (v)}=2922 (w, CH), 2849 (w, CH), 1690 (s, CO), 1655 (m, arom. C═C), 1600 (w, arom. C═C), 1478 (w), 1420 (w), 1338 (w), 1208 (m), 1131 (m), 1067 (w), 1002 (m), 955 (w), 932 (w), 794 (m), 717 (m); 1H NMR (300.5 MHz, CDCl3): δ=2.30 (s, 12H, CH3), 4.31 (s, 8H, CH2), 7.62–7.69 (m, 8H, ArH), 8.05–8.13 (m, 8H, ArH), 8.92 (s, 8H, β-pyrrole); LD-MS calcd av mass 1028.15 (C56H44N4O4S4Zn), obsd 1028.8, 986.6 [M+−COCH3], 954.7 [M+−SCOCH3], 911.3 [M+−SCOCH3—COCH3], 880.4 [M+−2 SCOCH3], 838.8 [M+−2 SCOCH3—COCH3], 805.3 [M+−3 SCOCH3]; λab's(toluene) 424, 550, 589 nm; λem (toluene) 597, 647 nm.

Provenance & Evidence