Synthesis and optical resolution of a fluorescent chiral calix[4]arene with two pyrene moieties forming an intramolecular excimer

Abstract

An inherently fluorescent chiral calix[4]arene 2 with two pyrene moieties forming an intramolecular pyrene excimer has been synthesized and optically resolved by an HPLC method using a chiral-packed column.

References

1. For reviews on calixarenes, see: C. D. Gutshe, Calixarenes, The Royal Society of Chemistry, Cambridge, England, 1989; Calixarenes: A Versatile Class of Macrocyclic Compounds, ed. V. Böhmer and J. Vincens, Kluwer, Dordrecht, 1991.
2. K. Araki, K. Inada and S. Shinkai, Angew. Chem., Int. Ed. Engl., 1996, 35, 72; Y. Kubo, S. Maeda, S. Tokita and M. Kubo, Nature, 1996, 382, 522.
3. S. Shinkai, T. Arimura, H. Saitoh and O. Manabe, J. Chem. Soc., Chem. Commun., 1987, 1495; T. Arimura, S. Edamitsu, S. Sinkai, O. Manabe, T. Muramatsu and M. Tashiro, Chem. Lett., 1987, 2269; C. D. Gutshe and K. C. Nam, J. Am. Chem. Soc., 1988, 110, 6153; T. Arimura, H. Kuwabata, M. Matsuda, T. Muramatsu, H. Saitoh, K. Fujio, O. Manabe and S. Shinkai, J. Org. Chem., 1991, 56, 301; A. Marra, M.-C. Scherrmann, A. Dondoni, A. Casnati, P. Minari and R. Ungaro, Angew. Chem., 1994, 106, 2533; Angew. Chem., Int. Ed. Eng., 1994, 33, 2479; P. Nari, A. Bottino, C. Geraci and M. Piattelli, Tetrahedron: Asymmetry, 1996, 7, 17.
4. (a) K. Iwamoto, A. Yanagi, T. Arimura, T. Matsuda and S. Shinkai, Chem. Lett., 1990, 1901; (b) S. Pappalardo, S. Caccamese and L. Giunta, Tetrahedron. Lett., 1991, 32, 7747; (c) K. Iwamoto, H. Shimizu, K. Araki and S. Shinkai, J. Am. Chem. Soc., 1993, 115, 3997; (d) G. Ferguson, J. F. Gallagher, L. Glunta, P. Neri and S. Pappalardo, J. Org. Chem., 1994, 59, 42; (e) S. Pappalardo, G. Ferguson, P. Neri and C. Rocco, J. Org. Chem., 1995, 60, 4576.
5. (a) H. Casabianca, J. Royer, A. Satrallah, A. Taty-C and J. Vicens, Tetrahedron Lett., 1987, 28, 6595; (b) S. Shinkai, T. Arimura, H. Kuwabata, H. Murakami, K. Araki, K. Iwamoto and T. Matsuda, J. Chem. Soc., Chem. Commun., 1990, 1734; (c) S. Shinkai, T. Arimura, H. Kuwabata, H. Murakami and K. Iwamoto, J. Chem. Soc., Perkin Trans. 1, 1991, 2429; (d) P. A. Reddy and C. D. Gutshe, J. Org. Chem., 1993, 58, 3245; (e) G. D. Andreetti, V. Böhmer, J. G. Jordan, M. Tabatabai, F. Ugozzoli, W. Vogt and A. Wolff, J. Org. Chem., 1993, 58, 4023; (f) W. Verboom, P. J. Bodewes, G. van Essen, P. Timmerman, G. J. Van Hummel, S. Harkema and D. N. Reinhouldt, Tetrahedron, 1995, 51, 499; (g) A. Ikeda, M. Yoshimura, P. Lhotak and S. Shinkai, J. Chem. Soc., Perkin Trans. 1, 1996, 1945.
6. W. R. Ware, Time-Resolved Fluorescence Spectroscopy in Biochemistry, ed. R. B. Cundall and R. E. Dale, Plenum, New York, 1983, p. 341; T. Jin, K. Ichikawa and T. Koyama, J. Chem. Soc., Chem, Commun., 1992, 499.
7. C. D. Gutsche, B. Dhawam, J. A. Levine, K. Hyun and L. J. Bauer, Tetrahedron, 1983, 39, 409; K. Iwamoto, K. Araki and S. Shinkai, Terahedron, 1991, 47, 4325.