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HETEROCYCLES, Vol. 77, No. 2, 2009
REFERENCES
1. "The Porphyrin Handbook," Vols. 15-20, ed. by K. M. Kadish, K. M. Smith, and R. Guilard,
Academic Press, San Diego, 2003; "Phthalocyanines: Properties and Applications," Vols. 1-4, ed. by
C. C. Leznoff and A. B. P. Lever, VCH, New York, 1989-1996.
2. H. Kliesch, A. Weitemeyer, S. Müller, and D. Wöhrle, Liebigs Ann., 1995, 1269; U. Michelsen, H.
Kliesch, G. Schnurpfeil, A. K. Sobbi, and D. Wöhrle, Photochem. Photobiol., 1996, 64, 694.
3. N. Kobayashi, R. Kondo, S. Nakajima, and T. Osa, J. Am. Chem. Soc., 1990, 112, 9640; N.
Kobayashi, T. Ishizaki, K. Ishii, and H. Konami, J. Am. Chem. Soc., 1999, 121, 9096.
4. D. Wöhrle and G. Krawczyk, Polymer Bull., 1986, 15, 193; C. C. Leznoff, P. I. Svirskaya, B. Khouw,
R. L. Cerny, P. Seymour, and A. B. P. Lever, J. Org. Chem., 1991, 56, 82.
5. Compounds (1) and (2) were prepared by the methods described in the literature; a) T. Kimura, A.
Yomogita, T. Matsutani, T. Suzuki, I. Tanaka, Y. Kawai, Y. Takaguchi, T. Wakahara, and T. Akasaka,
J. Org. Chem., 2004, 69, 4716; b) M. Kohn, J. Am. Chem. Soc., 1951, 73, 480.
1
6. 4a: mp 240-242 °C; H NMR (400 MHz, CDCl ) δ –3.72 (s, 2H, NH), 1.20-1.26 (m, 18H, CH ),
3
3
1.78 (t, J = 7.3 Hz, 6H, CH ), 1.81-1.92 (m, 12H, CH ), 2.12-2.24 (m, 12H, CH ), 4.42-4.56 (m, 12H,
3
2
2
OCH ), 4.45-4.52 (m, 4H, CH ), 4.63 (s, 4H, SCH ), 7.29-7.64 (m, 10H, ArH), 8.15 (s, 2H, ArH),
2
2
2
+
1
8.20 (s, 2H, ArH), 8.21 (s, 2H, ArH); FAB MS (m/z) 1247.6 (MH ); 5a: mp 224-226 °C; H NMR
(400 MHz, CDCl ) δ –2.66 (s, 2H, NH), 1.09-1.21 (m, 12H, CH ), 1.70-1.84 (m, 8H, CH ), 1,93 (t,
3
3
2
J=7.1 Hz, 12H, CH ), 2.08-2.22 (m, 8H, CH ), 4.47 (t, J = 6.6 Hz, 4H, OCH ), 4.54 (t, J = 6.5 Hz,
3
2
2
4H, OCH ), 4.65 (s, 4H, SCH ), 4.67 (s, 4H, SCH ), 4.78-4.93 (m, 8H, CH ), 7.20-7.61 (m, 20H,
2
2
2
2
+
1
ArH), 8.30 (s, 2H, ArH), 8.55 (s, 2H, ArH); FAB MS (m/z) 1403.6 (MH ); 6a: mp 78-80 °C; H
NMR (400 MHz, CDCl ) δ –2.02 (s, 2H, NH), 1.18 (t, J = 7.4 Hz, 12H, CH ), 1.74-1.83 (m, 8H,
3
3
CH ), 1.86 (t, J = 7.3 Hz, 12H, CH ), 2.10-2.19 (m, 8H, CH ), 4.53 (s, 8H, SCH ), 4.57 (t, J = 6.5 Hz,
2
3
2
2
8H, OCH ), 4.71-4.79 (m, 8H, CH ), 7.16-7.39 (m, 12H, Ar), 7.46 (d, J = 7.2 Hz, 8H, Ar), 8.67 (s,
2
2
+
1
4H, Ar), ESIMS (m/z) 1403.68 (MH ); 7a: mp 212-214 °C; H NMR (400 MHz, CDCl ) δ –0.41 (s,
3
2H, NH), 1.17 (t, J = 7.4 Hz, 6H, CH ), 1.57 (t, J = 7.4 Hz, 12H, CH ), 1.78 (sext, J = 7.4 Hz, 4H,
3
3
CH ), 1.94 (t, J = 7.3 Hz, 6H, CH ), 2.11-2.19 (m, 4H, CH ), 4.47 (s, 4H, SCH ), 4.50 (s, 8H, SCH ),
2
3
2
2
2
4.59 (t, J = 6.6 Hz, 4H, OCH ), 4.62-4.86 (m, 4H, CH ), 7.14-7.43 (m, 30H, ArH), 8.79 (s, 2H, Ar);
2
2
+
FABMS (m/z) 1559.6 (MH ).
1
7. 4b: mp 228-231 °C; H NMR (400 MHz, CDCl ) δ -3.33 (br, 2H, NH), 1.18-1.30 (m, 18H, CH ),
3
3
1.76 (t, J = 7.1 Hz, 6H, CH ), 1.79-1.94 (m, 12H, CH ), 2.11-2.26 (m, 12H, CH ), 4.41-4.63 (m, 16H,
3
2
2
OCH , ArCH ), 4.64 (s, 4H, SCH ), 7.21-7.28 (m, 2H, ArH), 7.32 (t, J = 7.2 Hz, 4H, ArH), 7.52 (d, J
2
2
2
77
= 7.2 Hz, 4H, ArH), 8.24 (s, 2H, ArH), 8.28 (s, 2H, ArH), 8.31 (s, 2H, ArH); Se NMR (76 MHz,
+
CDCl ) δ 236.2; FAB MS (m/z) 1342.57 (MH ); UV-vis (CHCl ) λ
= 621, 654, 683, 702, and
3
3
max
721 nm.
1
8. 8: H NMR (400 MHz, CDCl ) δ 1.23 (t, J = 7.5 Hz, 6H), 3.14 (t, J = 7.5 Hz, 4H), 7.49 (br, 1H);
3
+
HRMS Calcd for C H NO S , 296.9952. Found, (m/z) 296.9958 (M ).
12 11 2 3