Supramolecular dendritic solubilisation of a hydrophilic dye and tuning of its optical properties

Abstract

Dendritic peptides with a carboxylic acid at the focal point of the branched structure specifically solubilise a polybasic aromatic dye, the microenvironment and optical properties of which are controlled by the size (generation) of the branched peptide.

References

1. For reviews of dendrimer chemistry see: G. R. Newkome, C. N. Moorefield and F. Vögtle, Dendritic Molecules: Concepts, Syntheses, Perspectives, VCH, Weinheim, 1996; H.-F. Chow, T. K.-K. Mong, M. F. Nongrum and C.-W. Wan, Tetrahedron, 1998, 54, 8543; O. A. Matthews, A. N. Shipway and J. F. Stoddart, Prog. Polym. Sci., 1998, 23, 1.
2. For general reviews of supramolecular dendrimer chemistry see: F. W. Zeng and S. C. Zimmerman, Chem. Rev., 1997, 97, 1681; V. V. Narayanan and G. R. Newkome, Top. Curr. Chem., 1998, 197, 20.
3. For reports of self assembling dendrimers see: S. C. Zimmerman, F. Zeng, D. E. C. Reichert and S. V. Kolotuchin, Science, 1996, 271, 1095; V. Percec, W.-D. Cho, P. E. Mosier, G. Ungar and D. J. P. Yeardley, J. Am. Chem. Soc., 1998, 120, 11061; Y. Wang, F. Zeng and S. C. Zimmerman, Tetrahedron Lett., 1997, 31, 5459; M. Kawa and J. M. J. Fréchet, Chem. Mater., 1998, 10, 286 For a general review see: T. Emrick and J. M. J. Fréchet, Curr. Opin. Colloid Interface Sci., 1999, 4, 15.
4. For reports of spherical dendrimers solubilising dyes see: (a) G. R. Newkome, C. N. Moorefield, G. R. Baker, M. J. Saunders and S. H. Grossman, Angew. Chem., Int. Ed. Engl., 1991, 30, 1178; (b) C. J. Hawker, K. L. Wooley and J. M. J. Fréchet, J. Chem. Soc., Perkin Trans. 1, 1993, 1287; (c) J. F. G. A. Jansen, E. M. M. de brabander-van den Berg and E. W. Meijer, Science, 1944, 266, 1226; (d) S. Stevelmans, J. C. M. van Hest, J. F. G. A. Jansen, D. A. F. J. van Boxtel, E. M. M. de Brabander-van den Berg and E. W. Meijer, J. Am. Chem. Soc., 1996, 118, 7398; (e) M. W. P. L. Baars, P. E. Froehling and E. W. Meijer, Chem. Commun., 1997, 1959; (f) A. I. Cooper, J. D. Londono, G. Wignall, J. B. McClain, E. T. Samulski, J. S. Lin, A. Dobrynin, M. Rubinstein, A. L. C. Burke, J. M. J. Fréchet and J. M. DeSimone, Nature, 1998, 389, 368.
5. (a) C. J. Hawker, K. L. Wooley and J. M. J. Fréchet, J. Am. Chem. Soc., 1993, 115, 4375; (b) S. Mattei, P. Seiler, F. Diederich and V. Gramlich, Helv. Chim. Acta, 1995, 78, 1904; (c) C. Devadoss, P. Bharathi and J. S. Moore, Angew. Chem., Int. Ed. Engl., 1997, 36, 1633.
6. D. K. Smith and F. Diederich, Chem. Bur. J., 1998, 4, 1353 and references therein.
7. R. G. Denkewalter, J. Kolc and W. J. Lukasavage, US Pat., 4 289 872, 1981, assigned to Allied Corp; J. P. Tam, Proc. Natl. Acad. Sci. U.S.A., 1988, 85, 5409.
8. Such acid–base interactions have recently been used for complexation both on the surface and in the interior of spherical PAMAM dendrimers: V. Chechik, M. Zhao and R. M. Crooks, J. Am. Chem. Soc., 1999, 121, 4910; L. J. Twyman, A. E. Beezer, R. Esfand, M. J. Hardy and J. C. Mitchell, Tetrahedron Lett., 1999, 40, 1743.
9. C. Seel and F. Vögtle, Angew. Chem., Int. Ed. Engl., 1991, 30, 442.
10. K. Yamaoka and M. Shimadzu, Bull. Chem. Soc. Jpn., 1983, 56, 55.
11. T. Liljefors and P.-O. Norrby, J. Am. Chem. Soc., 1997, 119, 1052.
12. The application of branched molecules to the field of drug delivery is an area of intense current activity, see: K. Uhrich, Trends Polym. Sci., 1997, 5, 388 and references therein.