Research Article

Synthesis, Spectroscopic, and Biological Studies on New Zirconium(IV) Porphyrins with Axial Ligand

Table 4

1H NMR data of free base porphyrin and their zirconium(IV) porphyrins complexes in CDCl3 at 298 K.

CompoundPorphyrin's δ, ppmSalicylate protons δ, ppm
N–Hβ-HMeso-H

TPP−2.76 (s, 2H)8.82 (s, 8H)8.27 (s, 8H, Ho)
7.60 (s, 12H, Hm,p)

Cl2ZrTPP8.87 (s, 8H)8.32 (d, 4H, Ho)
8.04 (d, 4H, Ho)
7.64 (s, 12H, Hm,p)

SAZrTPP8.93 (s, 8H)8.50 (s, 4H, Ho)
8.07 (d, 4H, Ho)
7.68 (m, 12H, Hm,p)
6.06 (d, H6)
6.18 (q, H5)
6.98 (q, H4)
6.16 (m, H3)

5-SSAZrTPP8.96 (s, 8H)8.53 (s, 4H, Ho)
8.11 (s, 4H, Ho)
7.71 (m, 12H, Hm,p)
7.19 (s, 1H, H6)
7.15 (d, 1H, H3)
7.10 (q, 1H, H4)

p-CH3TPP−2.75 (s, 2H)8.78 (s, 8H)8.18 (s, 8H, Ho)
7.56 (s, 8H, Hm)
2.64 (s, 12H, HCH3)

Cl2Zr(p-CH3TPP)8.80 (s, 8H)8.28 (d, 4H, Ho)
8.00 (s, 4H, Ho)
7.65 (s, 8H, Hm)
2.70 (s, 12H, HCH3)

SAZr(p-CH3TPP)8.94 (s, 8H)8.42 (d, 4H, Ho)
8.15 (m, 4H, Ho)
7.71 (m, 8H, Hm)
2.83 (s, 12H, )
6.04 (d, H6)
6.22 (q, H5)
6.93 (q, H4)
6.15 (d, H3)

5-SSAZr(p-CH3TPP)8.96 (s, 8H)8.47 (s, 4H, Ho)
8.18 (s, 4H, Ho)
7.78 (m, 8H, Hm)
2.85 (s, 12H, )
7.17 (s, 1H, H6)
7.08 (d, 1H, H3)
7.06 (q, 1H, H4)

p-ClTPP−2.75 (s, 2H)8.73 (s, 8H)8.25 (s, 4H, Ho)
7.75 (s, 4H, Hp)

Cl2Zr(p-ClTPP)8.97 (s, 8H)8.33 (d, 4H, Ho)
8.13 (s, 4H, Ho)
7.59 (s, 8H, Hm)

SAZr(p-ClTPP)9.12 (s, 8H)8.42 (d, 4H, Ho)
8.17 (m, 4H, Ho)
8.02 (m, 8H, Hm)
6.16 (d, H6)
6.30 (q, H5)
6.98 (q, H4)
6.26 (d, H3)

5-SSAZr(p-ClTPP)9.25 (s, 8H)8.46 (s, 4H, Ho)
8.23 (s, 4H, Ho)
8.09 (s, 8H, Hm)
7.20 (s, 1H, H6)
7.15 (d, 1H, H3)
7.09 (q, 1H, H4)

p-NO2TPP−2.84 (s, 2H)8.83 (s, 8H)8.68 (s, 8H, Ho)
8.41 (s, 8H, Hm)

Cl2Zr(p-NO2TPP)9.05 (s, 8H)8.42 (d, 4H, Ho)
8.04 (d, 4H, Ho)
7.79 (s, 8H, Hm)

SAZr(p-NO2TPP)9.17 (s, 8H)8.42 (s, 4H, Ho)
8.07 (d, 4H, Ho)
7.64 (s, 8H, Hm)
6.18 (d, H6)
6.55 (q, H5)
7.05 (q, H4)
6.52 (d, H3)

5-SSAZr(p-NO2TPP)9.26 (s, 8H)8.45 (s, 4H, Ho)
8.11 (s, 4H, Ho)
7.65 (s, 8H, Hm)
7.92 (s, 1H, H6)
7.78 (d, 1H, H3)
7.23 (q, 1H, H4)