Liu et al.
9
4H), −2.74 (s, 2H); UV/Vis (CHCl3): λmax =269nm (II J=7.4Hz, 2H), 7.66 (d, J=7.6Hz, 6H), 7.51 (d, J=7.7Hz,
band); 421nm (Soret band); 519, 556, 595, and 650nm (Q 3H), 7.23 (d, J=7.9Hz, 2H), 6.66 (s, 1H), 6.59 (s, 1H), 6.47
bands); fluorescence (CHCl3): λex =417nm, λem =656nm; (s, 1H), 4.59−4.20 (m, 4H), 2.46 (s, 2H); UV/Vis (CHCl3):
+
MS (MALDI-TOF): m/z calcd for C68H56N4O8 1056.41
λ
max =269nm (II band); 417nm (Soret band); 529nm (Q
[M+H]+, found 1056.38.
band);MS(MALDI-TOF):m/zcalcdforC62H39Cl3N4NiO5
+
5-Hydroxy-2-phenyl-7-(2-(4-(10,15,20-tris(4- 1082.13 [M+H]+, found 1082.14.
hydroxyphenyl)porphyrin-5-yl)phenoxy)ethoxy)-4H-
Nickel(II)5-Hydroxy-2-phenyl-7-(4-(4-(10,15,20-
chromen-4-one (4a) Yield 16%. 1H NMR (500MHz, tris(4-chlorophenyl)porphyrin-5-yl)phenoxy)butoxy)-
1
DMSO-d6): δ=12.88 (s, 1H), 9.98 (s, 3H), 8.86 (d, 4H-chromen-4-one (5c) Yield 19%. H NMR (500MHz,
J=11.9Hz, 8H), 8.14 (d, J=6.3Hz, 4H), 8.00 (d, J=7.9Hz, CDCl3): δ=12.75 (s, 1H), 8.80 (d, J=4.9Hz, 2H),
6H), 7.71−7.56 (m, 3H), 7.43 (d, J=8.2Hz, 2H), 7.21 (d, 8.73−8.69 (m, 6H), 7.91 (t, J=8.4Hz, 8H), 7.86 (d,
J=8.1Hz, 6H), 7.10 (s, 1H), 7.02 (s, 1H), 6.59 (s, 1H), 4.65 J=7.0Hz, 2H), 7.66 (d, J=8.1 Hz, 6H), 7.52−7.45 (m,
(t, J=6.2Hz, 2H), 4.56 (t, J=6.2Hz, 2H), −2.90 (s, 2H); 3H), 7.21 (d, J=8.4Hz, 2H), 6.65 (s, 1H), 6.54 (d, J=1.9Hz,
UV/Vis (CHCl3): λmax =269nm (II band); 421nm (Soret 1H), 6.43 (d, J=1.9Hz, 1H), 4.29 (d, J=5.0Hz, 2H), 4.20
band); 519, 556, 594, and 650nm (Q bands); fluorescence (d, J=5.2Hz, 2H), 2.15 (d, J=2.3Hz, 4H); UV/Vis
(CHCl3): λex =417nm, λem =656nm; MS (MALDI-TOF): (CHCl3): λmax =269nm (II band); 417nm (Soret band);
m/z calcd for C61H42N4O8+ 958.30 [M+H]+, found 958.17. 529nm (Q band); MS (MALDI-TOF): m/z calcd for
5-Hydroxy-2-phenyl-7-(4-(4-(10,15,20-tris(4- C63H41Cl3N4NiO5+ 1096.15 [M+H]+, found 1096.17.
hydroxyphenyl)porphyrin-5-yl)phenoxy)butoxy)-4H-
Nickel(II)5-Hydroxy-2-phenyl-7-((5-(4-(10,15,20-
chromen-4-one (4b) Yield 16%. 1H NMR (500MHz, tris(4-chlorophenyl)porphyrin-5-yl)phenoxy)pentyl)
DMSO-d6): δ=12.81 (s, 1H), 9.95 (s, 3H), 8.87 (d, oxy)-4H-chromen-4-one (5d) Yield 18%. 1H NMR
J=5.7Hz, 6H), 8.83 (s, 2H), 8.08 (dd, J=14.7, 7.8Hz, 4H), (500MHz, CDCl3): δ=12.73 (s, 1H), 8.80 (d, J=4.9Hz,
8.01−7.94 (m, 6H), 7.54 (dt, J=15.1, 7.2Hz, 3H), 7.35 (d, 2H), 8.74−8.68 (m, 6H), 7.91 (dd, J=11.7, 8.4Hz, 8H),
J=8.2Hz, 2H), 7.21 (d, J=8.0Hz, 6H), 6.99 (d, J=14.4Hz, 7.82 (d, J=7.2Hz, 2H), 7.65 (d, J=8.1Hz, 6H), 7.53−7.44
1H), 6.86 (d, J=2.3Hz, 1H), 6.46 (d, J=2.1Hz, 1H), (m, 3H), 7.21 (d, J=8.4Hz, 2H), 6.60 (s, 1H), 6.51 (d,
4.32−4.20 (m, 4H), 2.04 (s, 4H), −2.88 (s, 2H); UV/Vis J=2.1Hz, 1H), 6.40 (d, J=2.1Hz, 1H), 4.24 (t, J=6.2Hz,
(CHCl3): λmax =269nm (II band); 421nm (Soret band); 2H), 4.12 (t, J=6.3Hz, 2H), 2.06−1.96 (m, 4H), 1.85−1.77
519, 556, 594, and 650nm (Q bands); fluorescence (CHCl3): (m, 2H); UV/Vis (CHCl3): λmax =269nm (II band); 417nm
λex =417nm, λem =656nm; MS (MALDI-TOF): m/z calcd (Soret band); 529nm (Q band); MS (MALDI-TOF): m/z
for C63H46N4O8+ 986.33 [M+H]+, found 986.21.
calcd for C64H43Cl3N4NiO5 1110.17 [M+H]+, found
+
5-Hydroxy-2-phenyl-7-((6-(4-(10,15,20-tris(4- 1110.18.
hydroxyphenyl)porphyrin-5-yl)phenoxy)hexyl)oxy)-
4H-chromen-4-one (4c) Yield 18%. H NMR (500MHz, tris(4-chlorophenyl)porphyrin-5-yl)phenoxy)hexyl)
Nickel(II)5-Hydroxy-2-phenyl-7-((6-(4-(10,15,20-
1
DMSO-d6): δ=12.81 (s, 1H), 9.98 (s, 3H), 8.87 (s, 6H), oxy)-4H-chromen-4-one (5e) Yield 21%. 1H NMR
8.83 (s, 2H), 8.09 (d, J=8.2Hz, 2H), 8.05 (d, J=7.5Hz, (500MHz, CDCl3): δ=12.72 (s, 1H), 8.80 (d, J=4.7Hz,
2H), 8.02−7.98 (m, 6H), 7.59−7.48 (m, 3H), 7.35 (d, 2H), 8.74−8.68 (m, 6H), 7.91 (t, J=9.6Hz, 8H), 7.80 (d,
J=8.3Hz, 2H), 7.20 (d, J=8.1Hz, 6H), 7.00 (s, 1H), 6.86 J=7.5Hz, 2H), 7.65 (d, J=7.9Hz, 6H), 7.52−7.41 (m,
(s, 1H), 6.43 (s, 1H), 4.26 (t, J=6.1Hz, 2H), 4.17 (t, 3H), 7.21 (d, J=8.1Hz, 2H), 6.58 (s, 1H), 6.48 (s, 1H), 6.39
J=6.3Hz, 2H), 1.96−1.89 (m, 2H), 1.88−1.80 (m, 2H), (s, 1H), 4.21 (t, J=6.0Hz, 2H), 4.08 (t, J=6.2Hz, 2H),
1.61 (dd, J=15.4, 9.9Hz, 4H), −2.91 (s, 2H); UV/Vis 2.03−1.96 (m, 2H), 1.96−1.89 (m, 2H), 1.74−1.62 (m,
(CHCl3): λmax =269nm (II band); 421nm (Soret band); 4H); UV/Vis (CHCl3): λmax =269nm (II band); 417nm
519, 556, 594, and 650nm (Q bands); fluorescence (CHCl3): (Soret band); 529nm (Q band); MS (MALDI-TOF): m/z
+
λex =417nm, λem =656nm; MS (MALDI-TOF): m/z calcd calcd for C65H45Cl3N4NiO5 1124.18 [M+H]+, found
for C65H50N4O8+ 1014.36 [M+H]+, found 1014.23.
1124.19.
Nickel(II)5-Hydroxy-2-phenyl-7-(2-(4-(10,15,20-
Nickel(II)5-Hydroxy-2-phenyl-7-(2-(4-(10,15,20-
tris(4-chlorophenyl)porphyrin-5-yl)phenoxy)ethoxy)- tris(4-methoxyphenyl)porphyrin-5-yl)phenoxy)
1
4H-chromen-4-one (5a) Yield 16%. H NMR (500MHz, ethoxy)-4H-chromen-4-one (6a) Yield 15%. 1H NMR
CDCl3): δ=12.75 (s, 1H), 8.79 (d, J=4.4Hz, 2H), 8.72 (d, (500MHz, CDCl3): δ=12.78 (s, 1H), 8.80−8.68 (m, 8H),
J=6.4Hz, 6H), 7.93 (t, J=8.5Hz, 9H), 7.89 (d, J=7.4Hz, 7.92 (q, J=8.3Hz, 10H), 7.58−7.47 (m, 3H), 7.21 (d,
2H), 7.67 (d, J=7.6Hz, 6H), 7.52 (d, J=7.7Hz, 3H), 7.24 J=8.5Hz, 8H), 6.70 (s, 1H), 6.65 (d, J=2.0Hz, 1H), 6.52
(d, J=7.9Hz, 2H), 6.68 (s, 1H), 6.60 (s, 1H), 6.48 (s, 1H), (d, J=2.0Hz, 1H), 4.55 (d, J=10.1Hz, 4H), 4.04 (s, 9H);
4.43−4.36 (m, 4H); UV/Vis (CHCl3): λmax =269nm (II UV/Vis (CHCl3): λmax =269nm (II band); 419nm (Soret
band); 417nm (Soret band); 529nm (Q band); MS band); 530nm (Q band); MS (MALDI-TOF): m/z calcd for
+
(MALDI-TOF): m/z calcd for C61H37Cl3N4NiO5 1068.12 C64H46N4NiO8+ 1056.27 [M+H]+, found 1056.25.
[M+H]+, found 1068.13.
Nickel(II)5-Hydroxy-2-phenyl-7-(3-(4-(10,15,20-
Nickel(II)5-Hydroxy-2-phenyl-7-(3-(4-(10,15,20- tris(4-methoxyphenyl)porphyrin-5-yl)phenoxy)
1
tris(4-chlorophenyl)porphyrin-5-yl)phenoxy)propoxy)- propoxy)-4H-chromen-4-one (6b) Yield 16%. H NMR
1
1
4H-chromen-4-one (5b) Yield 15%. H NMR (500MHz, (500MHz, CDCl3) H NMR (500MHz, CDCl3): δ=12.77
CDCl3): δ=12.74 (s, 1H), 8.78 (d, J=4.4Hz, 2H), (s, 1H), 8.87 (d, J=5.3Hz, 8H), 8.14 (d, J=7.2Hz, 8H),
8.73−8.68 (m, 6H), 7.91 (t, J=8.5Hz, 8H), 7.88 (d, 7.94−7.90 (m, 2H), 7.53 (d, J=6.9Hz, 3H), 7.30 (d,