Polycationic Dendrimers

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 24, 1997, Pages 2781-2783

  Ashton, Peter R ^b   Shibata, Kazusato ^b   Shipway, Andrew N ^b   Stoddart, J Fraser ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF BIRMINGHAM   (United Kingdom)

Author keywords

Dendrimers; Menschutkin reaction; Polycations; Polyelectrolytes

Indexed keywords

EID: 0032491868     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199727811     Document Type: Article

References (34)

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2. a) D. A. Tomalia, A. M. Naylor, W. A. Goddard III, Angew. Chem. 1990, 102, 119-157; Angew. Chem. Int. Ed. Engl. 1990, 29, 138-175;
3. b) G. R. Newkome, C. N. Moorefield, F. Vögtle, Dendritic Molecules, VCH, Weinheim, 1996;
4. c) O. A. Matthews, A. N. Shipway, J. F. Stoddart, Prog. Polym. Sci., 1998, 23, 1-56.
5. Many dendrimers with polyanionic surfaces have been synthesized, see for example a) K. R. Gopidas, A. R. Leheny, G. Caminati, N. J. Turro, D. A. Tomalia, J. Am. Chem. Soc. 1991, 113, 7335-7342; b) C. J. Hawker, K. L. Wooley, J. M. J. Fréchet, J. Chem. Soc. Perkin Trails. 1 1993, 1287-1297.
6. Many dendrimers with polyanionic surfaces have been synthesized, see for example a) K. R. Gopidas, A. R. Leheny, G. Caminati, N. J. Turro, D. A. Tomalia, J. Am. Chem. Soc. 1991, 113, 7335-7342; b) C. J. Hawker, K. L. Wooley, J. M. J. Fréchet, J. Chem. Soc. Perkin Trails. 1 1993, 1287-1297.
7. Apart from cationic sites being introduced into an organic compound during its synthesis, polycalionic dendrimers have been produced by a) modification of neutral dendrimers (see for example C. Larré, A.-M. Caminade, J.-P. Majoral, Angew. Chem. 1997, 109, 614-617; Angew. Chem. Int. Ed. Engl. 1997, 36, 596-599) and b) incorporating transition matals into the dendritic structure (see for example S. Campagna, G. Dendti, S. Serroni, A. Juris, M. Venturi, V. Ricevuto, V. Balzani, Chem. Eur. J. 1995 1, 211-221; S. Achar, J. Puddephatt, J. Chem. Soc. Chem. Commun. 1994, 1895-1896).
8. Apart from cationic sites being introduced into an organic compound during its synthesis, polycalionic dendrimers have been produced by a) modification of neutral dendrimers (see for example C. Larré, A.-M. Caminade, J.-P. Majoral, Angew. Chem. 1997, 109, 614-617; Angew. Chem. Int. Ed. Engl. 1997, 36, 596-599) and b) incorporating transition matals into the dendritic structure (see for example S. Campagna, G. Dendti, S. Serroni, A. Juris, M. Venturi, V. Ricevuto, V. Balzani, Chem. Eur. J. 1995 1, 211-221; S. Achar, J. Puddephatt, J. Chem. Soc. Chem. Commun. 1994, 1895-1896).
9. Apart from cationic sites being introduced into an organic compound during its synthesis, polycalionic dendrimers have been produced by a) modification of neutral dendrimers (see for example C. Larré, A.-M. Caminade, J.-P. Majoral, Angew. Chem. 1997, 109, 614-617; Angew. Chem. Int. Ed. Engl. 1997, 36, 596-599) and b) incorporating transition matals into the dendritic structure (see for example S. Campagna, G. Dendti, S. Serroni, A. Juris, M. Venturi, V. Ricevuto, V. Balzani, Chem. Eur. J. 1995 1, 211-221; S. Achar, J. Puddephatt, J. Chem. Soc. Chem. Commun. 1994, 1895-1896).
10. Apart from cationic sites being introduced into an organic compound during its synthesis, polycalionic dendrimers have been produced by a) modification of neutral dendrimers (see for example C. Larré, A.-M. Caminade, J.-P. Majoral, Angew. Chem. 1997, 109, 614-617; Angew. Chem. Int. Ed. Engl. 1997, 36, 596-599) and b) incorporating transition matals into the dendritic structure (see for example S. Campagna, G. Dendti, S. Serroni, A. Juris, M. Venturi, V. Ricevuto, V. Balzani, Chem. Eur. J. 1995 1, 211-221; S. Achar, J. Puddephatt, J. Chem. Soc. Chem. Commun. 1994, 1895-1896).
11. J.-J. Lee, W. T. Ford. J. A. Moore, Y. Li. Macromolecules 1994, 27, 4632-4634.
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15. Although many diverse examples of catalytic dendrimers have been reported, they rely upon the incorporation of a known catalytic site inside or on the surface of the dendritic structure rather than upon the unique dendritic microenvironment itself, see for example a) J. W. J. Knapen, A. W. van der Made, J. C. de Wilde, P. W. N. M. van Leeuwen, P. Wijkens, D. M. Grove, G. van Koten, Nature 1994, 372, 659-663; b) A. Miedaner, C. J. Curtis, R. M. Barkley, D. L. DuBois, Inorg. Chem. 1994, 33, 5482-5490; c) P. J. Dandliker, F. Diederich, J.-P. Gisselbrecht, A. Louati, M. Gross, Angew. Chem. 1995, 107, 2906-2909; Angew. Chem. Int. Ed. Engl. 1995, 54, 2725-2727.
16. Although many diverse examples of catalytic dendrimers have been reported, they rely upon the incorporation of a known catalytic site inside or on the surface of the dendritic structure rather than upon the unique dendritic microenvironment itself, see for example a) J. W. J. Knapen, A. W. van der Made, J. C. de Wilde, P. W. N. M. van Leeuwen, P. Wijkens, D. M. Grove, G. van Koten, Nature 1994, 372, 659-663; b) A. Miedaner, C. J. Curtis, R. M. Barkley, D. L. DuBois, Inorg. Chem. 1994, 33, 5482-5490; c) P. J. Dandliker, F. Diederich, J.-P. Gisselbrecht, A. Louati, M. Gross, Angew. Chem. 1995, 107, 2906-2909; Angew. Chem. Int. Ed. Engl. 1995, 54, 2725-2727.
17. Although many diverse examples of catalytic dendrimers have been reported, they rely upon the incorporation of a known catalytic site inside or on the surface of the dendritic structure rather than upon the unique dendritic microenvironment itself, see for example a) J. W. J. Knapen, A. W. van der Made, J. C. de Wilde, P. W. N. M. van Leeuwen, P. Wijkens, D. M. Grove, G. van Koten, Nature 1994, 372, 659-663; b) A. Miedaner, C. J. Curtis, R. M. Barkley, D. L. DuBois, Inorg. Chem. 1994, 33, 5482-5490; c) P. J. Dandliker, F. Diederich, J.-P. Gisselbrecht, A. Louati, M. Gross, Angew. Chem. 1995, 107, 2906-2909; Angew. Chem. Int. Ed. Engl. 1995, 54, 2725-2727.
18. Although many diverse examples of catalytic dendrimers have been reported, they rely upon the incorporation of a known catalytic site inside or on the surface of the dendritic structure rather than upon the unique dendritic microenvironment itself, see for example a) J. W. J. Knapen, A. W. van der Made, J. C. de Wilde, P. W. N. M. van Leeuwen, P. Wijkens, D. M. Grove, G. van Koten, Nature 1994, 372, 659-663; b) A. Miedaner, C. J. Curtis, R. M. Barkley, D. L. DuBois, Inorg. Chem. 1994, 33, 5482-5490; c) P. J. Dandliker, F. Diederich, J.-P. Gisselbrecht, A. Louati, M. Gross, Angew. Chem. 1995, 107, 2906-2909; Angew. Chem. Int. Ed. Engl. 1995, 54, 2725-2727.
19. For examples of the encapsulation of guest molecules inside dendritic structures, see a) A. M. Taylor, W. M. Goddard III, G. E. Keifer, D. A. Tomalia, J. Am. Chem. Soc. 1989, 111, 2339-2341; b) G. R. Newkome, C. N. Moorefield, G. R. Baker, M. J. Saunders, S. H. Grossman, Angew. Chem. 1991, 103, 1207-1209; Angew. Chem. Int. Ed. Engl. 1991, 30, 1178-1180; c) C. J. Hawker, K. L. Wooley, J. M. J. Fréchet, J. Chem. Soc. Perkin Trans. 1 1993, 1287-1297; d) J. F. G. A. Jansen, E. M. M. de Brabander-van den - Berg, E. W. Meijer, Science 1994, 266, 1226-1229; e) J. F. G. A. Jansen, E. W. Meijer, E. M. M. de Brabander-van den Berg, J. Am. Chem. Soc. 1995, 117, 4417-4418.
20. For examples of the encapsulation of guest molecules inside dendritic structures, see a) A. M. Taylor, W. M. Goddard III, G. E. Keifer, D. A. Tomalia, J. Am. Chem. Soc. 1989, 111, 2339-2341; b) G. R. Newkome, C. N. Moorefield, G. R. Baker, M. J. Saunders, S. H. Grossman, Angew. Chem. 1991, 103, 1207-1209; Angew. Chem. Int. Ed. Engl. 1991, 30, 1178-1180; c) C. J. Hawker, K. L. Wooley, J. M. J. Fréchet, J. Chem. Soc. Perkin Trans. 1 1993, 1287-1297; d) J. F. G. A. Jansen, E. M. M. de Brabander-van den - Berg, E. W. Meijer, Science 1994, 266, 1226-1229; e) J. F. G. A. Jansen, E. W. Meijer, E. M. M. de Brabander-van den Berg, J. Am. Chem. Soc. 1995, 117, 4417-4418.
21. For examples of the encapsulation of guest molecules inside dendritic structures, see a) A. M. Taylor, W. M. Goddard III, G. E. Keifer, D. A. Tomalia, J. Am. Chem. Soc. 1989, 111, 2339-2341; b) G. R. Newkome, C. N. Moorefield, G. R. Baker, M. J. Saunders, S. H. Grossman, Angew. Chem. 1991, 103, 1207-1209; Angew. Chem. Int. Ed. Engl. 1991, 30, 1178-1180; c) C. J. Hawker, K. L. Wooley, J. M. J. Fréchet, J. Chem. Soc. Perkin Trans. 1 1993, 1287-1297; d) J. F. G. A. Jansen, E. M. M. de Brabander-van den - Berg, E. W. Meijer, Science 1994, 266, 1226-1229; e) J. F. G. A. Jansen, E. W. Meijer, E. M. M. de Brabander-van den Berg, J. Am. Chem. Soc. 1995, 117, 4417-4418.
22. For examples of the encapsulation of guest molecules inside dendritic structures, see a) A. M. Taylor, W. M. Goddard III, G. E. Keifer, D. A. Tomalia, J. Am. Chem. Soc. 1989, 111, 2339-2341; b) G. R. Newkome, C. N. Moorefield, G. R. Baker, M. J. Saunders, S. H. Grossman, Angew. Chem. 1991, 103, 1207-1209; Angew. Chem. Int. Ed. Engl. 1991, 30, 1178-1180; c) C. J. Hawker, K. L. Wooley, J. M. J. Fréchet, J. Chem. Soc. Perkin Trans. 1 1993, 1287-1297; d) J. F. G. A. Jansen, E. M. M. de Brabander-van den - Berg, E. W. Meijer, Science 1994, 266, 1226-1229; e) J. F. G. A. Jansen, E. W. Meijer, E. M. M. de Brabander-van den Berg, J. Am. Chem. Soc. 1995, 117, 4417-4418.
23. For examples of the encapsulation of guest molecules inside dendritic structures, see a) A. M. Taylor, W. M. Goddard III, G. E. Keifer, D. A. Tomalia, J. Am. Chem. Soc. 1989, 111, 2339-2341; b) G. R. Newkome, C. N. Moorefield, G. R. Baker, M. J. Saunders, S. H. Grossman, Angew. Chem. 1991, 103, 1207-1209; Angew. Chem. Int. Ed. Engl. 1991, 30, 1178-1180; c) C. J. Hawker, K. L. Wooley, J. M. J. Fréchet, J. Chem. Soc. Perkin Trans. 1 1993, 1287-1297; d) J. F. G. A. Jansen, E. M. M. de Brabander-van den Berg, E. W. Meijer, Science 1994, 266, 1226-1229; e) J. F. G. A. Jansen, E. W. Meijer, E. M. M. de Brabander-van den Berg, J. Am. Chem. Soc. 1995, 117, 4417-4418.
24. For examples of the encapsulation of guest molecules inside dendritic structures, see a) A. M. Taylor, W. M. Goddard III, G. E. Keifer, D. A. Tomalia, J. Am. Chem. Soc. 1989, 111, 2339-2341; b) G. R. Newkome, C. N. Moorefield, G. R. Baker, M. J. Saunders, S. H. Grossman, Angew. Chem. 1991, 103, 1207-1209; Angew. Chem. Int. Ed. Engl. 1991, 30, 1178-1180; c) C. J. Hawker, K. L. Wooley, J. M. J. Fréchet, J. Chem. Soc. Perkin Trans. 1 1993, 1287-1297; d) J. F. G. A. Jansen, E. M. M. de Brabander-van den - Berg, E. W. Meijer, Science 1994, 266, 1226-1229; e) J. F. G. A. Jansen, E. W. Meijer, E. M. M. de Brabander-van den Berg, J. Am. Chem. Soc. 1995, 117, 4417-4418.
25. Examples of catalyses have been observed in cationic micelles (F. M. Menger, L. G. Whitesell, J. Am. Chem. Soc. 1985, 107, 707-708) and in polymerized micelles (A. Kumar, G. Oehme, J. P. Roque, M. Schwarze, R. Selke, Angew. Chem. 1994, 106, 2272-2274; Angew. Chem. Int. Ed. Engl. 1994, 33, 2197-2199).
26. Examples of catalyses have been observed in cationic micelles (F. M. Menger, L. G. Whitesell, J. Am. Chem. Soc. 1985, 107, 707-708) and in polymerized micelles (A. Kumar, G. Oehme, J. P. Roque, M. Schwarze, R. Selke, Angew. Chem. 1994, 106, 2272-2274; Angew. Chem. Int. Ed. Engl. 1994, 33, 2197-2199).
27. Examples of catalyses have been observed in cationic micelles (F. M. Menger, L. G. Whitesell, J. Am. Chem. Soc. 1985, 107, 707-708) and in polymerized micelles (A. Kumar, G. Oehme, J. P. Roque, M. Schwarze, R. Selke, Angew. Chem. 1994, 106, 2272-2274; Angew. Chem. Int. Ed. Engl. 1994, 33, 2197-2199).
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29. 2 rather than a phenoxide group. For this reason, the two systems should be compatible in the construction of mixed-monomer dendritic architectures.
30. The nomenclature employed for describing the wedges and dendrimers: a number (0, 1, 2, or 3) denoting the generation followed by the letter G for generation, and thereafter by the letter W or D for a wedge or a dendrimer, respectively.
31. 4 followed by reduction of the triester affords 1,3,5-tris(hydroxymethyl)benzene in quantitative yield.
32. 3 (0.7 mL) was essentially unchanged after heating at 100°C for 72 h.
33. K. L. Wooley, C. J. Hawker, J. M. J. Fréchet, J. Am. Chem. Soc. 1991, 113, 4252-4261.
34. S. A. Kuzdzal, C. A. Monnig, G. R. Newkome, C. N. Moorefield, J. Am. Chem. Soc. 1997, 119, 2255-2261.