Synthesis of Bridged Oligophenylenes from Fluorene. Part 1. Ter- and Quater-phenyls

Abstract

Alkylation and halogenation of fluorene give halogenated 9,9-dialkylfluorenes, which are converted by Pd-catalysed coupling with aryl Grignard reagents into a series of ter- and quater-phenyls exhibiting strongly efficient fluorescence, useful solubility and photochemical stability.

References

1. (a) M. Rinke, H. Gusten and H. J. Ache, J. Phys. Chem., 1986, 90, 2661 (and references cited therein); (b) M. Rinke, H. Gusten and H. J. Ache, J. Phys. Chem., 1986, 90, 2666.
2. (a) H. O. Wirth, K. H. Gonner and W. Kern, Makromol. Chem., 1963, 63, 30; (b) H. O. Wirth, K. H. Gonner, R. Stuck and W. Kern, Makromol. Chem., 1963, 63, 53; (c) H. O. Wirth, G. Waese and W. Kern, Makromol. Chem., 1965, 86, 139.
3. (a) J. M. Kauffman, C. J. Kelley, A. Ghiorghis, E. Neister, L. Armstrong and P. Prause, Laser Chem., 1987, 7, 343; (b) J. M. Kauffman, C. J. Kelley, A. Ghiorghis, E. Neister and L. Armstrong, Laser Chem., 1988, 8, 335; (c) P. A. Fleitz, C. J. Seliskar, R. N. Steppel, J. M. Kauffman, C. J. Kelley and A. Ghiorghis, Laser Chem., 1991, 11, 99; (d) C. J. Seliskar, D. A. Landis, J. M. Kauffman, M. A. Aziz, R. N. Steppel, C. J. Kelley, Y. Qin and A. Ghiorghis, Laser Chem., 1993, 13, 19; (e) J. M. Kauffman, P. Litak, J. A. Novinski, C. J. Kelley, A. Ghiorghis and Y. Qin, J. Fluorescence, 1995, 5, 295.
4. J. M. Kauffman and C. J. Kelley, in preparation.
5. A. Minato, K. Tamao, T. Hayashi, K. Suzuki and M. Kumada, Tetrahedron Lett., 1981, 22, 5319.