A novel pyrenophane incorporating macrocyclic tetraazathiapentalene is synthesised and characterised. The absorption and fluorescence spectra in CH2Cl2 clearly showed π–π interaction between two pyrene rings including pyrene excimer emission.
De SilvaA.P., GunaratneH. Q. N., and McCoyC. P., 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.
MiharaH., TanakaY., FujimotoT., and NishinoN., 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.
3.
DeSchryberF.C., CollartP., VandendriesscheJ., GoedeweeckR., SwinnenA., and Von Der AuweraerM., Acc Chem, Res., 1987, 20, 159; D. Declercq, P. Delbeke, F.C. DeSchryver, L. Van Meervelt 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.
4.
(a) AokiI., HaradaT., SakakiT., KawaharaY., and ShinkaiS., J. Chem. Soc., Chem. Commun., 1992, 1341.
5.
InouyeM., FujimotoK., FrusyoM., and NakazumiH., J. Am. Chem. Soc., 1999, 121, 1452.
UmemotoT., SataniS., SakatY., and MisumiS., 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.
8.
MatsumuraN., TomuraM., MoriO., UkawaM., and YonedaS., Heterocycles, 1987, 26, 3097; N. Matsumura, R. Hirase and H. Inoue, Tetrahedron Lett., 1994, 35, 899.
9.
MatsumuraN., KonishiT., HayashiH., YasuiM., IwasakiF., and MizunoK., Heterocycles, 2000, 53, 1239; N. Matsumura, T. Konishi, H. Hayashi, M. Yasui, F. Iwasaki and K. Mizuno, J. Heterocyclic Chem., 2002, 39, 189.
Fluorescence lifetimes of 1, 2, and 3 in CH2Cl2 were obtained by single photon counting method (HORIBA NAES-550). 1; 20 and 6 ns, 2; 19 ns, 3; 31 ns.
12.
Recently, we have reported the PET reaction of tetraazathiapentalene with trialkylamines; HayashiH., MatsumuraN., and MizunoK., Chem. Lett., 2002, 510.
13.
MOPAC version 97; CS MOPAC., Tokyo and CAChe 3.2 for windows, Fujitsu, co., Tokyo.