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(0.42). 1H NMR (500 MHz, CDCl3): δ, ppm 9.22 (s, 1H,
10-H), 9.07 (s, 1H, 5-H), 8.81 (s, 1H, 134-H), 8.52 (s,
1H, 20-H), 8.09 (d, J = 8.6 Hz, 2H, Ph-H), 7.75 (dd, J =
17.9, 11.7 Hz, 1H, 31-H), 7.05 (d, J = 8.7 Hz, 2H, Ph-H),
6.19 (d, J = 17.9 Hz, 1H, 32-H), 6.08 (d, J = 11.5 Hz, 1H,
32-H), 5.31 (dd, J = 9.2, 2.2 Hz, 1H, 17-H), 4.35 (q, J =
7.3 Hz, 1H, 18-H), 3.9, 3.64, 3.54, 3.28 (each s, each 3H,
OCH3 + CH3), 3.33 (q, J = 7.9 Hz, 2H, 81-CH2), 2.93 (s,
3H, 4-Ph-OCH3), 2.82–2.71 (m, 1H, 171a-H), 2.54–2.38
(m, 2H, 171b + 172a-H), 2.03–1.95 (m, 1H, 172b-H), 1.73
(d, J = 7.3 Hz, 3H, 18-CH3), 1.51 (t, J = 7.6 Hz, 3H,
82-CH3), -0.06 (br s, 1H, NH), -0.16 (br s, 1H, NH). Anal.
calcd. for C42H42N6O5: C 70.97; H 5.96; N 11.82. Found:
C 70.99; H 5.95; N 11.80.
Purpurinimide-hydrazone conjugate 9. Yield: 88%,
mp 127–129 °C. UV-vis (CHCl3): λmax, nm (rel. intensity
log ε) 422 (1.00), 514 (0.13), 553 (0.28), 651 (0.15), 710
(0.45). 1H NMR (500 MHz, CDCl3): δ, ppm 9.44 (s, 1H,
10-H), 9.24 (s, 1H, 5-H), 8.88 (s, 1H, 134-H), 8.53 (s, 1H,
20-H), 8.07 (m, 2H, Ph-H), 7.85 (dd, J = 17.8, 11.5 Hz,
1H, 31-H), 7.57-7.50 (m, 2H, Ph-H), 6.27 (dd, J = 17.8,
1.2 Hz, 1H, 32-H), 6.15 (dd, J = 11.5, 1.2 Hz, 1H, 32-H),
5.29 (dd, J = 9.2, 2.4 Hz, 1H, 17-H), 4.34 (q, J = 7.2 Hz,
1H, 18-H), 3.73, 3.54, 3.33, 3.08 (each s, each 3H, OCH3 +
CH3), 3.52 (q, J = 8.0 Hz, 2H, 81-CH2), 2.78–2.70 (m,
1H, 171a-H), 2.51–2.36 (m, 2H, 171b + 172a-H), 2.08-1.93
(m, 1H, 172b-H), 1.71 (d, J = 7.3 Hz, 3H, 18-CH3), 1.60
(t, J = 7.7 Hz, 3H, 82-CH3), 0.15 (br s, 1H, NH), 0.03 (br
s, 1H, NH). Anal. calcd. for C41H39ClN6O4: C 68.85; H
5.50; N 11.75. Found: C 68.90; H 5.51; N 11.77.
Purpurinimide-hydrazone conjugate 10. Yield: 88%,
mp 135–137 °C. UV-vis (CHCl3): λmax, nm (rel. intensity
log ε) 422 (1.00), 514 (0.13), 554 (0.27), 651 (0.14), 712
(0.43). 1H NMR (500 MHz, CDCl3): δ, ppm 9.55 (s, 1H,
10-H), 9.30 (s, 1H, 5-H), 8.67 (s, 1H, 134-H), 8.54 (s, 1H,
20-H), 8.01–7.96 (m, 2H, Ph-H), 7.87 (dd, J = 17.8, 11.5
Hz, 1H, 31-H), 6.82–6.77 (m, 2H, Ph-H), 6.27 (dd, J =
17.8, 1.3 Hz, 1H, 32-H), 6.14 (dd, J = 11.5, 1.3 Hz, 1H,
32-H), 5.32 (dd, J = 9.2, 2.6 Hz, 1H, 17-H), 4.34 (q, J =
7.3 Hz, 1H, 18-H), 3.80, 3.53, 3.33, 3.12 (each s, each
3H, OCH3 + CH3), 3.60 (q, J = 7.6 Hz, 2H, 81-CH2), 3.11
(s, 6H, Ph-N(CH3)2), 2.76–2.70 (m, 1H, 171a-H), 2.52–
2.35 (m, 2H, 171b + 172a-H), 2.04–1.93 (m, 1H, 172b-H),
1.69 (d, J = 7.3 Hz, 3H, 18-CH3), 1.64 (t, J = 7.7 Hz, 3H,
82-CH3), 0.11 (br s, 1H, NH), -0.01 (br s, 1H, NH). Anal.
calcd. for C43H6.27N7O4: C 71.35; H 6.27; N 13.54. Found:
C 71.37; H 6.28; N 13.52.
Purpurinimide-hydrazone conjugate 11. Yield: 86%,
mp 145-147 °C. UV-vis (CHCl3): λmax, nm (rel. intensity
log ε) 422 (1.00), 513 (0.11), 552 (0.26), 651 (0.12), 708
(0.40). 1H NMR (500 MHz, CDCl3): δ, ppm 9.20 (s, 1H,
10-H), 9.10 (s, 1H, 5-H), 8.90 (s, 1H, 134-H), 8.52 (s,
1H, 20-H), 8.26–8.21 (m, 2H, Ph-H), 8.11–8.07 (m, 2H,
Ph-H), 7.77 (dd, J = 17.8, 11.5 Hz, 1H, 31-H), 6.22 (dd,
J = 17.8, 1.0 Hz, 1H, 32-H), 6.11 (dd, J = 11.5, 1.0 Hz,
1H, 32-H), 5.29 (dd, J = 9.3, 2.2 Hz, 1H, 17-H), 4.36 (q,
J = 7.4 Hz, 1H, 18-H), 3.59, 3.55, 3.30, 2.96 (each s,
each 3H, OCH3 + CH3), 3.35 (q, J = 7.6 Hz, 2H, 81-CH2),
2.81–2.72 (m, 1H, 171a-H), 2.52–2.41 (m, 2H, 171b
+
172a-H), 2.00 (m, 2H, 172b-H), 1.77 (d, J = 7.3 Hz, 3H,
18-CH3), 1.52 (t, J = 7.7 Hz, 3H, 82-CH3), 0.03 (br s, 1H,
NH), -0.08 (br s, 1H, NH). Anal. calcd. for C41H39N7O6:
C 67.85; H 5.42; N 13.51. Found: C 67.88; H 5.45; N
13.49.
Purpurinimide-hydrazone conjugate 12. Yield: 89%,
mp 175–177 °C. UV-vis (CHCl3): λmax, nm (rel. intensity
log ε) 422 (1.00), 513 (0.09), 552 (0.24), 651 (0.10), 710
(0.40). 1H NMR (500 MHz, CDCl3): δ, ppm 9.56 (s, 1H,
10-H), 9.49 (s, 1H, 5-H), 9.23 (s, 1H, 134-H), 8.64 (dd,
J = 7.7, 1.5 Hz, 1H, 6′-Ph-H), 8.53 (s, 1H, 20-H), 8.24 (dd,
J = 8.4, 1.2 Hz, 1H, 3′-Ph-H), 7.83 (dd, J = 17.8, 11.5 Hz,
1H, 31-H), 7.89–7.84 (m, 1H, 5’-Ph-H), 7.78–7.71 (m,
1H, 4′-Ph-H), 6.26 (dd, J = 17.8, 1.2 Hz, 1H, 32-H), 6.14
(dd, J = 11.5, 1.2 Hz, 1H, 32-H), 5.27 (dd, J = 9.2, 2.2 Hz,
1H, 17-H), 4.35 (q, J = 7.3 Hz, 1H, 18-H), 3.76, 3.54,
3.32, 3.08 (each s, each 3H, OCH3 + CH3), 3.55 (q,
J = 7.6 Hz, 2H, 81-CH2), 2.82–2.71 (m, 1H, 171a-H),
2.53–2.40 (m, 2H, 171b + 172a-H), 2.06-1.94 (m, 1H,
172b-H), 1.71 (d, J = 7.4 Hz, 3H, 18-CH3), 1.62 (t, J =
7.7 Hz, 3H, 82-CH3), 0.21 (br s, 1H, NH), 0.06 (br s, 1H,
NH). Anal. calcd. for C41H39N7O6: C 67.85; H 5.42; N
13.51. Found: C 67.84; H 5.44; N 13.55.
Purpurinimide-hydrazone conjugate 13. Yield: 82%,
mp 141–142 °C. UV-vis (CHCl3): λmax, nm (rel. inten-
sity log ε) 422 (1.00), 514 (0.14), 552 (0.28), 651 (0.15),
710 (0.46). 1H NMR (500 MHz, CDCl3): δ, ppm 9.49 (s,
1H, 10-H), 9.24 (s, 1H, 5-H), 9.22 (s, 1H, 134-H), 8.53
(s, 1H, 20-H), 7.82 (dd, J = 17.8, 11.5 Hz, 1H, 31-H),
7.50 (d, J = 8.3 Hz, 2H, 4,6-Ph-H), 7.36 (dd, J = 8.6, 7.7
Hz, 1H, 5-Ph-H), 6.25 (dd, J = 17.8, 1.1 Hz, 1H, 32-H),
6.12 (dd, J = 11.5, 1.2 Hz, 1H, 32-H), 5.31 (dd, J = 9.2,
2.2 Hz, 1H, 17-H), 4.36 (q, J = 7.5 Hz, 1H, 18-H), 3.79,
3.55, 3.32, 3.07 (each s, each 3H, OCH3 + CH3), 3.54 (q,
J = 8.0 Hz, 2H, 81-CH2), 2.83–2.72 (m, 1H, 171a-H),
2.56–2.40 (m, 2H, 171b + 172a-H), 2.08–1.94 (m, 1H,
172b-H), 1.72 (d, J = 7.3 Hz, 3H, 18-CH3), 1.62 (t, J =
7.7 Hz, 3H, 82-CH3), 0.13 (br s, 1H, NH), -0.02 (br s, 1H,
NH). Anal. calcd. for C41H38Cl2N6O4: C 65.69; H 5.11; N
11.21. Found: C 65.75; H 5.14; N 11.23.
Purpurinimide-hydrazone conjugate 14. Yield: 91%,
mp 155–157 °C. UV-vis (CHCl3): λmax, nm (rel. inten-
sity log ε) 422 (1.00), 514 (0.12), 553 (0.27), 651 (0.12),
1
711 (0.43). H NMR (500 MHz, CDCl3): δ, ppm 9.31
(s, 1H, 10-H), 9.10 (s, 1H, 5-H), 8.75 (s, 1H, 134-H),
8.52 (s, 1H, 20-H), 7.96 (s, 2H, 3',5'-Ph-H), 7.76 (dd, J =
17.8, 11.5 Hz, 1H, 31-H), 6.20 (dd, J = 17.8, 1.2 Hz, 1H,
32-H), 6.08 (dd, J = 11.5, 1.2 Hz, 1H, 32-H), 5.70 (br s,
1H, OH), 5.33 (dd, J = 9.2, 2.7 Hz, 1H, 17-H), 4.35 (q, J =
7.3 Hz, 1H, 18-H), 3.70, 3.54, 3.29, 2.96 (each s, each
3H, OCH3 + CH3), 3.39 (q, J = 7.6 Hz, 2H, 81-CH2),
2.79-2.70 (m, 1H, 171a-H), 2.55-2.36 (m, 2H, 171b
+
172a-H), 2.05–1.96 (m, 1H, 172b-H), 1.72 (d, J = 7.4
Hz, 3H, 18-CH3), 1.54 (t, J = 7.6 Hz, 3H, 82-CH3), 1.53
(s, 18H, 2′,6′-C(CH3)3), -0.04 (br s, 1H, NH), -0.15 (br s,
Copyright © 2011 World Scientific Publishing Company
J. Porphyrins Phthalocyanines 2011; 15: 266–270