Hydrophobically modified poly(amidoamine) (PAMAM) dendrimers: their properties at the air–water interface and use as nanoscopic container molecules

Abstract

Tri- and tetra-dendron poly(amidoamine) (PAMAM) dendrimers were converted into hydrocarbon-soluble polymers and used as hydrophobic nanoscopic scaffolding by reacting their primary amino chain ends with various epoxyalkanes. These hydrophobically modified modules performed well as nanoscopic transport molecules. They mimicked classical inverse micelle behaviour by transporting copper(ii) sulfate from an aqueous solution into an organic phase to form homogeneous, transparent, intensely blue toluene solutions. The modified dendrimers were examined at the air–water interface both with and without copper guest molecules. A number of critical macromolecular design parameters (CMDPs) such as generation (size), core (shape, topology) and surface groups were varied to determine their influence on Langmuir film properties.

References

1. (a) P. R. Dvornic and D. A. Tomalia, Science Spectra, 1996, 5, 36; (b) J. M. J. Fréchet, Science, 1994, 263, 1710.
2. L. J. de Jongh, in Physics and Chemistry of Metal Cluster Compounds, ed. F. Levy, Kluwer Academic Publishers, Dordrecht, 1994.
3. P. R. Dvornic and D. A. Tomalia, Curr. Opin. Colloid Interface Sci., 1996, 1, 221.
4. (a) J.-M. Lehn, Supramolecular Chemistry, VCH, New York, 1995; (b) C. A. Mirkin, R. C. Mucic, J. J. Storhoff and R. L. Letsinger, Nature, 1996, 382, 607.
5. (a) A. Kumar, N. L. Abbott, E. Kim, H. A. Biebuyck and G. M. Whitesides, Acc. Chem. Res., 1995, 28, 219; (b) R. Dagani, ‘Nanoengineering’ in Chem. Eng. News, December 2, 1996, p. 20.
6. P. R. Dvornic and D. A. Tomalia, Chem. Br., 1994, 30, 641.
7. G. M. Whitesides, J. P. Mathias and C. T. Seto, Science, 1991, 254, 1312.
8. J. Dutta, H. Hofmann and G. Schmid, Adv. Mater., 1996, 8, 555.
9. R. Dagani, ‘Nanostructured Materials’ in Chem. Eng. News, November 23, 1992, p. 18.
10. D. A. Tomalia and H. D. Durst, in Top. Curr. Chem. Vol. 165: Supramolecular Chemistry I—Directed Synthesis and Molecular Recognition, ed. E. Weber, Springer-VerlagBerlin Heidelberg, 1993, pp. 193–313.
11. G. R. Newkome, C. N. Moorefield and F. Vögtle, in Dendritic molecules, ed. G. Walter, VCH, New York & Weinheim 1996.
12. (a) N. Ardoin and D. Astruc, Bull. Soc., Chim Fr., 1995, 132, 875; (b) D. Astruc, C.R. Acad. Sci. Paris, 1996, 322, 757.
13. B. I. Voit, Acta Polymer., 1995, 46, 87.
14. R. Yin, D. R. Swanson and D. A. Tomalia, Polym. Mater. Sci. Eng., 1995, 73, 277.
15. (a) D. A. Tomalia, J. R. Dewald, M. J. Hall, S. J. Martin and P. B. Smith, Preprints 1st SPSJ Int. Polym. Conf., Soc. of Polym. Sci.Japan, Kyoto, 1984, p. 65; (b) D. A. Tomalia, H. Baker, J. Dewald, M. Hall, G. Kallos, S. Martin, J. Roeck, J. Ryder and P. Smith, Polym. J. (Tokyo), 1985, 17, 117.
16. (a) D. A. Tomalia, Aldrichim. Acta, 1993, 26(4), 91; (b) D. A. Tomalia, Adv. Mater., 1994, 6, 529.
17. J. W. J. Knapen, A. W. van der Made, J. C. de Wilde, P. W. N. M. van Leeuwen, P. Wijkens, D. M. Grove and G. van Koten, Nature, 1994, 372, 659.
18. P. Bhyrappa, J. K. Young, J. S. Moore and K. S. Suslick, J. Mol. Catal. A: Chem., 1996, 113, 109.
19. M. X. Tang, C. T. Redemann and F. C. Szoka, Jr, Bioconj. Chem., 1996, 7, 703.
20. (a) J. F. Kukowska-Latallo, A. U. Bielinska, J. Johnson, R. Spindler, D. A. Tomalia and J. R. Baker, Jr, Proc. Natl. Acad. Sci. USA, 1996, 93, 4897; (b) A. Bielinska, J. Kukowska-Lattalo, L. T. Piehler, D. A. Tomalia, R. Yin and J. R. Baker, Jr, Polym. Mater. Sci. Eng., 1995, 73, 273.
21. A. Bielinska, J. F. Kukowska-Latallo, J. Johnson, D. A. Tomalia and J. R. Baker, Jr, Nucleic Acids Res., 1996, 24, 2176.
22. E. C. Wiener, M. W. Brechbiel, H. Brothers, R. L. Magin, O. A. Gansow, D. A. Tomalia and P. C. Lauterbur, Magn. Reson. Med., 1994, 31, 1.
23. (a) L. I. Miller, T. Hashimoto, I. Tabakovic, D. R. Swanson and D. A. Tomalia, Chem. Mater., 1995, 7, 9; (b) R. G. Duan, L. I. Miller and D. A. Tomalia, J. Am. Chem. Soc., 1995, 117, 10783.
24. (a) C. Devadoss, P. Bharathi and J. S. Moore, J. Am. Chem. Soc., 1996, 118, 9635; (b) Z. Xu and J. S. Moore, Acta Polym., 1994, 45, 83.
25. (a) J. F. G. A. Jansen, E. M. M. de Brabander-van den Berg and E. W. Meijer, Science, 1994, 266, 1226; (b) J. F. G. A. Jansen, E. W. Meijer and E. M. M. de Brabander-van den Berg, J. Am. Chem. Soc., 1995, 117, 4417; (c) J. F. G. A. Jansen, R. A. J. Janssen, E. M. M. de Brabander-van den Berg and E. W. Meijer, Adv. Mater., 1995, 7, 561.
26. (a) D. A. Tomalia, H. Baker, J. Dewald, M. Hall, G. Kallos, S. Martin, J. Roeck, J. Ryder and P. Smith, Macromolecules, 1986, 19, 2466; (b) D. A. Tomalia, V. Berry, M. Hall and D. M. Hedstrand, Macromolecules, 1987, 20, 1167; (c) D. A. Tomalia, M. Hall and D. M. Hedstrand, J. Am. Chem. Soc., 1987, 109, 1601.
27. (a) P. B. Smith, S. J. Martin, M. J. Hall and D. A. Tomalia, in Applied Polymer Analysis and Characterization, ed. J. Mitchell, Hanser, 1987, pp. 357–385; (b) G. J. Kallos, D. A. Tomalia, D. M. Hedstrand, S. Lewis and J. Zhou, Rapid Commun. Mass Spectrom., 1991, 5, 383; (c) P. R. Dvornic and D. A. Tomalia, Macromol. Symp., 1995, 98(35th IUPAC Int. Symp. Macromol., 1994), 403.
28. (a) C. J. Hawker, K. L. Wooley and J. M. J. Fréchet, J. Chem. Soc., Perkin Trans., 1, 1993, 1287; (b) C. J. Hawker and J. M. J. Fréchet, J. Chem. Soc., Perkin Trans., 1, 1992, 2459.
29. (a) K. L. Wooley, C. J. Hawker, J. M. Pochan and J. M. J. Fréchet, Macromolecules, 1993, 26, 1514; (b) E. M. M. de Brabander-van den Berg, A. Nijenhuis, M. Mure, J. Kuelen, R. Reintjens, F. Vandenbooren, B. Bosman, R. de Raat, T. Frijns, S. v. d. Wal, M. Castelijns, J. Put and E. W. Meijer, Macromol. Symp., 1994, 77, 51.
30. 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.
31. L. T. Piehler and D. A. Tomalia, Michigan Molecular Institute, unpublished results.
32. A. M. Naylor, W. A. Goddard III, G. E. Kiefer and D. A. Tomalia, J. Am. Chem. Soc., 1989, 111, 2339.
33. (a) D. A. Tomalia, A. M. Naylor and W. A. Goddard III, Angew. Chem., 1990, 102, 119; (b) Angew. Chem., Int. Ed. Engl., 1990, 29, 138.
34. (a) D. A. Tomalia, V. Berry, M. Hall and D. Hedstrand, Macromolecules, 1987, 20, 1164; (b) G. R. Newkome, C. N. Moorefield, G. R. Baker, M. J. Saunders and S. H. Grossman, Angew. Chem., 1991, 103, 1207; (c) K. L. Wooley, C. J. Hawker and J. M. J. Frèchet, J. Am. Chem. Soc., 1993, 115, 11496; (d) G. R. Newkome, J. K. Young, G. R. Baker, R. L. Potter, L. Audoly, D. Cooper and C. D. Weiss, Macromolecules, 1993, 26, 2394; (e) C. J. Hawker, K. L. Wooley and J. M. J. Fréchet, J. Chem. Soc., Perkin Trans., 1, 1993, 1287; (f) N. Tanaka, T. Tanigawa, K. Hosoya, K. Kimata, T. Araki and S. Teraba, Chem. Lett., 1992, 959; (g) S. A. Kuzdzal, C. A. Monning, G. R. Newkome and C. N. Moorefield, J. Chem. Soc., Chem. Commun., 1994, 2139; (h) P. G. H. M. Muijselaar, H. A. Claessens, C. A. Cramers, J. F. G. A. Jansen, E. W. Meijer, E. M. M. de Brabander-van den Berg and S. Van der Wal., J. High Resolut. Chromatogr., 1995, 18, 121.
35. V. U. Wege and R. H. Grubbs, Polym. Prepr. Am. Chem. Soc., Div. Polym. Chem., 1995, 36(2), 239.
36. M. C. Moreno-Bondi, G. Orellana, N. J. Turro and D. A. Tomalia, Macromolecules, 1990, 23, 910.
37. K. R. Gopidas, A. R. Leheny, G. Caminati, N. J. Turro and D. A. Tomalia, J. Am. Chem. Soc., 1991, 113, 7335.
38. M. F. Ottaviani, S. Bossman, N. J. Turro and D. A. Tomalia, J. Am. Chem. Soc., 1994, 116, 661.
39. M. F. Ottaviani, E. Cossu, N. J. Turro and D. A. Tomalia, J. Am. Chem. Soc., 1995, 117, 4387.
40. F. A. Cotton and G. Wilkinson, Advanced Inorganic Chemistry, Wiley, New York, 1980, pp. 815–817.
41. M. F. Ottaviani, F. Montalti, N. J. Turro and D. A. Tomalia, J. Phys. Chem. B, 1997, 101, 158.
42. (a) G. L. Gaines, Insoluble Monolayers at Liquid–Gas Interfaces, Interscience, New York, 1996, p. 264; (b) R. A. Hahn, in Langmuir–Blodgett Films, ed. G. Roberts, Plenum Press, New York, 1990, pp. 68–73.
43. R. H. G. Brinkhuis and A. J. Schouten, Langmuir, 1992, 8, 2247.
44. (a) X. Cha, R. Yin, X. Zhang and J. Shen, Macromolecules, 1991, 24, 4985; (b) S. Granick and J. Herz, Macromolecules, 1985, 18, 460.
45. I. R. Gentle, P. M. Saville, J. W. White and J. Penfold, Langmuir, 1993, 9, 646.
46. J. Kumaki, Macromolecules, 1988, 21, 749.
47. (a) P. M. Saville, J. W. White, C. J. Hawker, K. L. Wooley and J. M. J. Fréchet, J. Phys. Chem., 1993, 97, 293; (b) P. M. Saville, J. W. White, C. J. Hawker, J. M. J. Fréchet, K. L. Wooley, J. Penfold and J. R. P. Webster, J. Phys. Chem., 1995, 99, 8283.
48. R. Esfand, A. E. Beezer, J. C. Mitchell and I. J. Twyman, Pharm. Sci., 1996, 2, 1.