A novel pyrenophane bearing tetraazathiapentalene skeleton

Journal of Chemical Research

Volumn , Issue 9, 2004, Pages 599-601

  Hayashi, Hirokazu ^a   Matsumura, Noboru ^a   Mizuno, Kazuhiko ^a  

^a Osaka Prefecture University   (Japan)

Author keywords

Excimer; Pyrenophane; Tetraazathiapentalene

Indexed keywords

DICHLOROMETHANE; MACROCYCLIC COMPOUND; PYRENE DERIVATIVE; PYRENOPHANE; TETRAAZATHIAPENTALENE DERIVATIVE; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; ELECTRON TRANSPORT; EXCIMER LASER; FLUORESCENCE SPECTROSCOPY; INFRARED SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY ANALYSIS;

EID: 9644272806     PISSN: 03082342     EISSN: None     Source Type: Journal    
DOI: 10.3184/0308234042430368     Document Type: Article

References (29)

1. A.P. De Silva, H.Q.N. Gunaratne and C.P. McCoy, Nature, 1993, 364, 42; A.P. De Silva, H.Q.N. Gunaratne, T. Gunnlaugsson, A.J.M. Huxley, C.P. McCoy, J.T. Rademacher and T.E. Rice, Chem. Rev., 1997, 97, 1515; M. Enomoto and T. Aida, J. Synth. Org. Chem., Jpn., 1999, 57, 924; L. Fabbrizzi, M. Licchekki and P. Pallavicini, Acc. Chem. Res., 1999, 32, 846; M. Irie and K. Matsuda, J. Am. Chem. Soc., 2000, 122, 7195; S. Nishizawa, Y-Y. Cui, M. Minagawa, K. Morita, Y. Kato, S. Taniguchi, R. Kato and N. Teramae, J. Chem. Soc. Perkin Trans. 2, 2002, 866; T. Gunnlaugsson, A.P. Davis, G.M. Hussey, J. Tierney and M. Glynn, Org. Bioorg. Chem. 2004, 2, 1856.
2. A.P. De Silva, H.Q.N. Gunaratne and C.P. McCoy, Nature, 1993, 364, 42; A.P. De Silva, H.Q.N. Gunaratne, T. Gunnlaugsson, A.J.M. Huxley, C.P. McCoy, J.T. Rademacher and T.E. Rice, Chem. Rev., 1997, 97, 1515; M. Enomoto and T. Aida, J. Synth. Org. Chem., Jpn., 1999, 57, 924; L. Fabbrizzi, M. Licchekki and P. Pallavicini, Acc. Chem. Res., 1999, 32, 846; M. Irie and K. Matsuda, J. Am. Chem. Soc., 2000, 122, 7195; S. Nishizawa, Y-Y. Cui, M. Minagawa, K. Morita, Y. Kato, S. Taniguchi, R. Kato and N. Teramae, J. Chem. Soc. Perkin Trans. 2, 2002, 866; T. Gunnlaugsson, A.P. Davis, G.M. Hussey, J. Tierney and M. Glynn, Org. Bioorg. Chem. 2004, 2, 1856.
3. A.P. De Silva, H.Q.N. Gunaratne and C.P. McCoy, Nature, 1993, 364, 42; A.P. De Silva, H.Q.N. Gunaratne, T. Gunnlaugsson, A.J.M. Huxley, C.P. McCoy, J.T. Rademacher and T.E. Rice, Chem. Rev., 1997, 97, 1515; M. Enomoto and T. Aida, J. Synth. Org. Chem., Jpn., 1999, 57, 924; L. Fabbrizzi, M. Licchekki and P. Pallavicini, Acc. Chem. Res., 1999, 32, 846; M. Irie and K. Matsuda, J. Am. Chem. Soc., 2000, 122, 7195; S. Nishizawa, Y-Y. Cui, M. Minagawa, K. Morita, Y. Kato, S. Taniguchi, R. Kato and N. Teramae, J. Chem. Soc. Perkin Trans. 2, 2002, 866; T. Gunnlaugsson, A.P. Davis, G.M. Hussey, J. Tierney and M. Glynn, Org. Bioorg. Chem. 2004, 2, 1856.
4. A.P. De Silva, H.Q.N. Gunaratne and C.P. McCoy, Nature, 1993, 364, 42; A.P. De Silva, H.Q.N. Gunaratne, T. Gunnlaugsson, A.J.M. Huxley, C.P. McCoy, J.T. Rademacher and T.E. Rice, Chem. Rev., 1997, 97, 1515; M. Enomoto and T. Aida, J. Synth. Org. Chem., Jpn., 1999, 57, 924; L. Fabbrizzi, M. Licchekki and P. Pallavicini, Acc. Chem. Res., 1999, 32, 846; M. Irie and K. Matsuda, J. Am. Chem. Soc., 2000, 122, 7195; S. Nishizawa, Y-Y. Cui, M. Minagawa, K. Morita, Y. Kato, S. Taniguchi, R. Kato and N. Teramae, J. Chem. Soc. Perkin Trans. 2, 2002, 866; T. Gunnlaugsson, A.P. Davis, G.M. Hussey, J. Tierney and M. Glynn, Org. Bioorg. Chem. 2004, 2, 1856.
5. A.P. De Silva, H.Q.N. Gunaratne and C.P. McCoy, Nature, 1993, 364, 42; A.P. De Silva, H.Q.N. Gunaratne, T. Gunnlaugsson, A.J.M. Huxley, C.P. McCoy, J.T. Rademacher and T.E. Rice, Chem. Rev., 1997, 97, 1515; M. Enomoto and T. Aida, J. Synth. Org. Chem., Jpn., 1999, 57, 924; L. Fabbrizzi, M. Licchekki and P. Pallavicini, Acc. Chem. Res., 1999, 32, 846; M. Irie and K. Matsuda, J. Am. Chem. Soc., 2000, 122, 7195; S. Nishizawa, Y-Y. Cui, M. Minagawa, K. Morita, Y. Kato, S. Taniguchi, R. Kato and N. Teramae, J. Chem. Soc. Perkin Trans. 2, 2002, 866; T. Gunnlaugsson, A.P. Davis, G.M. Hussey, J. Tierney and M. Glynn, Org. Bioorg. Chem. 2004, 2, 1856.
6. A.P. De Silva, H.Q.N. Gunaratne and C.P. McCoy, Nature, 1993, 364, 42; A.P. De Silva, H.Q.N. Gunaratne, T. Gunnlaugsson, A.J.M. Huxley, C.P. McCoy, J.T. Rademacher and T.E. Rice, Chem. Rev., 1997, 97, 1515; M. Enomoto and T. Aida, J. Synth. Org. Chem., Jpn., 1999, 57, 924; L. Fabbrizzi, M. Licchekki and P. Pallavicini, Acc. Chem. Res., 1999, 32, 846; M. Irie and K. Matsuda, J. Am. Chem. Soc., 2000, 122, 7195; S. Nishizawa, Y-Y. Cui, M. Minagawa, K. Morita, Y. Kato, S. Taniguchi, R. Kato and N. Teramae, J. Chem. Soc. Perkin Trans. 2, 2002, 866; T. Gunnlaugsson, A.P. Davis, G.M. Hussey, J. Tierney and M. Glynn, Org. Bioorg. Chem. 2004, 2, 1856.
7. A.P. De Silva, H.Q.N. Gunaratne and C.P. McCoy, Nature, 1993, 364, 42; A.P. De Silva, H.Q.N. Gunaratne, T. Gunnlaugsson, A.J.M. Huxley, C.P. McCoy, J.T. Rademacher and T.E. Rice, Chem. Rev., 1997, 97, 1515; M. Enomoto and T. Aida, J. Synth. Org. Chem., Jpn., 1999, 57, 924; L. Fabbrizzi, M. Licchekki and P. Pallavicini, Acc. Chem. Res., 1999, 32, 846; M. Irie and K. Matsuda, J. Am. Chem. Soc., 2000, 122, 7195; S. Nishizawa, Y-Y. Cui, M. Minagawa, K. Morita, Y. Kato, S. Taniguchi, R. Kato and N. Teramae, J. Chem. Soc. Perkin Trans. 2, 2002, 866; T. Gunnlaugsson, A.P. Davis, G.M. Hussey, J. Tierney and M. Glynn, Org. Bioorg. Chem. 2004, 2, 1856.
8. H. Mihara, Y. Tanaka, T. Fujimoto and N. Nishino, J. Chem. Soc., Perkin. Trans. 2, 1995, 1915; D.Y. Sasaki and B.E. Padilla, J. Chem. Soc., Chem. Commun., 1998, 1581; H. Imahori, Y. Nishimura, H. Norieda, H. Karita, I. Yamazaki, Y. Sakata and S. Fukuzumi, J. Chem. Soc., Chem. Commun., 2000, 661.
9. H. Mihara, Y. Tanaka, T. Fujimoto and N. Nishino, J. Chem. Soc., Perkin. Trans. 2, 1995, 1915; D.Y. Sasaki and B.E. Padilla, J. Chem. Soc., Chem. Commun., 1998, 1581; H. Imahori, Y. Nishimura, H. Norieda, H. Karita, I. Yamazaki, Y. Sakata and S. Fukuzumi, J. Chem. Soc., Chem. Commun., 2000, 661.
10. H. Mihara, Y. Tanaka, T. Fujimoto and N. Nishino, J. Chem. Soc., Perkin. Trans. 2, 1995, 1915; D.Y. Sasaki and B.E. Padilla, J. Chem. Soc., Chem. Commun., 1998, 1581; H. Imahori, Y. Nishimura, H. Norieda, H. Karita, I. Yamazaki, Y. Sakata and S. Fukuzumi, J. Chem. Soc., Chem. Commun., 2000, 661.
11. F.C. DeSchryber, P. Collart, J. Vandendriessche, R. Goedeweeck, A. Swinnen and M. Von. Der Auweraer, Acc Chem, Res., 1987, 20, 159; D. Declercq, P. Delbeke, F.C. DeSchryver, L. Van Meerveit and R.D. Miller, J. Am. Chem. Soc., 1993, 115, 5702; K.A. Zachariasse and W. Kühnle, Zh. Phys. Chem., 1976, 101, 267; K.A. Zachariasse, G. Duveneck and W. Kühnle, Chem. Phys. Lett., 1985, 113, 337.
12. F.C. DeSchryber, P. Collart, J. Vandendriessche, R. Goedeweeck, A. Swinnen and M. Von. Der Auweraer, Acc Chem, Res., 1987, 20, 159; D. Declercq, P. Delbeke, F.C. DeSchryver, L. Van Meerveit and R.D. Miller, J. Am. Chem. Soc., 1993, 115, 5702; K.A. Zachariasse and W. Kühnle, Zh. Phys. Chem., 1976, 101, 267; K.A. Zachariasse, G. Duveneck and W. Kühnle, Chem. Phys. Lett., 1985, 113, 337.
13. F.C. DeSchryber, P. Collart, J. Vandendriessche, R. Goedeweeck, A. Swinnen and M. Von. Der Auweraer, Acc Chem, Res., 1987, 20, 159; D. Declercq, P. Delbeke, F.C. DeSchryver, L. Van Meerveit and R.D. Miller, J. Am. Chem. Soc., 1993, 115, 5702; K.A. Zachariasse and W. Kühnle, Zh. Phys. Chem., 1976, 101, 267; K.A. Zachariasse, G. Duveneck and W. Kühnle, Chem. Phys. Lett., 1985, 113, 337.
14. F.C. DeSchryber, P. Collart, J. Vandendriessche, R. Goedeweeck, A. Swinnen and M. Von. Der Auweraer, Acc Chem, Res., 1987, 20, 159; D. Declercq, P. Delbeke, F.C. DeSchryver, L. Van Meerveit and R.D. Miller, J. Am. Chem. Soc., 1993, 115, 5702; K.A. Zachariasse and W. Kühnle, Zh. Phys. Chem., 1976, 101, 267; K.A. Zachariasse, G. Duveneck and W. Kühnle, Chem. Phys. Lett., 1985, 113, 337.
15. (a) I. Aoki, T. Harada, T. Sakaki, Y. Kawahara and S. Shinkai, J. Chem. Soc., Chem. Commun., 1992, 1341;
16. (b) M. Inouye, K. Fujimoto, M. Frusyo and H. Nakazumi, J. Am. Chem. Soc., 1999, 121, 1452;
17. (c) T. Aoyagi, H. Ikeda and A. Ueno, Bull. Chem. Soc. Jpn., 2001, 74, 157.
18. T. Umemoto, S. Satani, Y. Sakat, and S. Misumi, Tetrahedron Lett., 1975, 3159; R.H. Mitchell, R.J. Corruthers and J.C.M. Zwinkels, Tetrahedron Lett., 1976, 2585; H.A. Staab and R.G.H. Kirrstetter, Liebigs, Ann, Chem., 1979, 886; A. Bilyk, M.M. Harding, P. Turner and T.W. Hanbley, J. Chem. Soc., Dalton. Trans., 1994, 2783.
19. T. Umemoto, S. Satani, Y. Sakat, and S. Misumi, Tetrahedron Lett., 1975, 3159; R.H. Mitchell, R.J. Corruthers and J.C.M. Zwinkels, Tetrahedron Lett., 1976, 2585; H.A. Staab and R.G.H. Kirrstetter, Liebigs, Ann, Chem., 1979, 886; A. Bilyk, M.M. Harding, P. Turner and T.W. Hanbley, J. Chem. Soc., Dalton. Trans., 1994, 2783.
20. T. Umemoto, S. Satani, Y. Sakat, and S. Misumi, Tetrahedron Lett., 1975, 3159; R.H. Mitchell, R.J. Corruthers and J.C.M. Zwinkels, Tetrahedron Lett., 1976, 2585; H.A. Staab and R.G.H. Kirrstetter, Liebigs, Ann, Chem., 1979, 886; A. Bilyk, M.M. Harding, P. Turner and T.W. Hanbley, J. Chem. Soc., Dalton. Trans., 1994, 2783.
21. T. Umemoto, S. Satani, Y. Sakat, and S. Misumi, Tetrahedron Lett., 1975, 3159; R.H. Mitchell, R.J. Corruthers and J.C.M. Zwinkels, Tetrahedron Lett., 1976, 2585; H.A. Staab and R.G.H. Kirrstetter, Liebigs, Ann, Chem., 1979, 886; A. Bilyk, M.M. Harding, P. Turner and T.W. Hanbley, J. Chem. Soc., Dalton. Trans., 1994, 2783.
22. N. Matsumura, M. Tomura, O. Mori, M. Ukawa and S. Yoneda, Heterocycles, 1987, 26, 3097; N. Matsumura, R. Hirase and H. Inoue, Tetrahedron Lett., 1994, 35, 899.
23. N. Matsumura, M. Tomura, O. Mori, M. Ukawa and S. Yoneda, Heterocycles, 1987, 26, 3097; N. Matsumura, R. Hirase and H. Inoue, Tetrahedron Lett., 1994, 35, 899.
24. N. Matsumura, T. Konishi, H. Hayashi, M. Yasui, F. Iwasaki, and K. Mizuno, Heterocycles, 2000, 53, 1239; N. Matsumura, T. Konishi, H. Hayashi, M, Yasui, F. Iwasaki and K. Mizuno, J. Heterocyclic Chem., 2002, 39, 189.
25. N. Matsumura, T. Konishi, H. Hayashi, M. Yasui, F. Iwasaki, and K. Mizuno, Heterocycles, 2000, 53, 1239; N. Matsumura, T. Konishi, H. Hayashi, M, Yasui, F. Iwasaki and K. Mizuno, J. Heterocyclic Chem., 2002, 39, 189.
26. N. Matsumura, M. Tomura, O. Mori, Y. Tsuchiya, S. Yoneda and K. Toriumi, Bull. Chem. Soc. Jpn, 1988, 61, 2419.
27. 2 were obtained by single photon counting method (HORIBA NAES-550). 1; 20 and 6 ns, 2; 19 ns, 3; 31 ns.
28. Recently, we have reported the PET reaction of tetraazathiapentalene with trialkylamines; H. Hayashi, N. Matsumura and K. Mizuno, Chem. Lett., 2002, 510.
29. MOPAC version 97; CS MOPAC., Tokyo and CAChe 3.2 for windows, Fujitsu, co., Tokyo.