Synthesis and characterization of π-conjugated oligomers that contain metal-to-ligand charge transfer chromophores†

Abstract

The synthesis and characterization of a series of p-phenyleneethynylene oligomers that contain the 2,2′-bipyridine-5,5′-diyl moiety is reported; metallation of the oligomers with Re^I(CO)₅Cl and Ru(bpy)₂Cl₂ yields the corresponding (L)Re(CO)₃Cl and (L)Ru(bpy)₂²⁺ complexes.

References

1. For leading reviews on π-conjugated polymers see: Handbook of Conducting Polymers, ed. T. A. Skotheim, R. L. Elsenbaumer and J. R. Reynolds, Marcel Dekker, New York, 2nd edn. 1998; H. Bassler and L. J. Rothberg, Chem. Phys., 1998, 227, 1; A. Kraft, A. C. Grimsdale and A. B. Holmes, Angew. Chem., Int. Ed., 1998, 37, 402; A. D. Schlüter and G. Wegner, Acta Polym., 1993, 44, 59.
2. (a) J. M. Tour, Chem. Rev., 1996, 96, 537; (b) L. R. Jones, J. S. Schumm and J. M. Tour, J. Org. Chem., 1997, 62, 1388; (c) J. S. Moore, Acc. Chem. Res., 1997, 30, 402; (d) M. Moroni, J. LeMoigne and S. Luzzati, Macromolecules, 1994, 27, 562; (e) U. Ziener and A. Godt, J. Org. Chem., 1997, 62, 6137; (f) H. Kukula, S. Veit and A. Godt, Eur. J. Org. Chem., 1999, 277.
3. K. D. Ley, C. E. Whittle, M. D. Bartberger and K. S. Schanze, J. Am. Chem. Soc., 1997, 119, 3423; K. D. Ley and K. S. Schanze, Coord. Chem. Rev., 1998, 171, 287; K. A. Walters, K. D. Ley and K. S. Schanze, Chem. Commun., 1998, 1115.
4. (a) Z. Peng and L. Yu, J. Am. Chem. Soc., 1996, 118, 3777; (b) S. C. Rasumssen, D. W. Thompson, V. Singh and J. D. Peterson, Inorg. Chem., 1996, 35, 3449; (c) Z. Peng, A. Gharavi and L. Yu, J. Am. Chem. Soc., 1997, 119, 4622; (d) B. Wang and M. R. Wasielewski, J. Am. Chem. Soc., 1997, 119, 12; (e) L. X. Chen, W. J. H. Jäger, M. P. Niemczyk and M. R. Wasielewski, J. Phys. Chem. A, 1999, 103, 4341.
5. K. Sonogashira, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 3, p. 521.
6. L. Della Ciana and A. Haim, J. Heterocycl. Chem., 1984, 21, 607; S. J. Havens and P. M. Hergenrother, J. Org. Chem., 1985, 50, 1763.
7. V. Grosshenny, F. M. Romero and R. Ziessel, J. Org. Chem., 1997, 62, 1491.