Designer dendrimers: Branched oligosulfonimides with controllable molecular architectures

Journal of the American Chemical Society

Volumn 128, Issue 27, 2006, Pages 8964-8974

  Lukin, Oleg ^a   Gramlich, Volker ^a   Kandre, Ramchandra ^a   Zhun, Igor ^a   Felder, Thorsten ^b,c   Schalley, Christoph A ^c   Dolgonos, Grigoriy ^d  

^a ETH ZURICH   (Switzerland)

^b UNIVERSITY OF BONN   (Germany)

^c FREIE UNIVERSITÄT BERLIN   (Germany)

^d Gina Cody School of Engineering and Computer Science   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; IONIZATION; MOLECULAR STRUCTURE; SINGLE CRYSTALS; SYNTHESIS (CHEMICAL);

DENDRONS; ELECTROSPRAY IONIZATION; OLIGOSULFONIMIDES;

DENDRIMERS;

BROMINE DERIVATIVE; DENDRIMER; FUNCTIONAL GROUP; IMIDE; OLIGOSULFONIMIDE; SULFONIMIDE; TERPHENYL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; DENSITY FUNCTIONAL THEORY; ELECTROSPRAY MASS SPECTROMETRY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID STATE; STEREOCHEMISTRY; SUZUKI REACTION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 33745969120     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja061606b     Document Type: Article

References (89)

1. For general reviews on dendrimers and dendrons, see: (a) Archut, A.; Vögtle, F. Chem. Soc. Rev. 1998, 27, 233-240.
2. (b) Smith, D. K.; Diederich, F. Chem. Eur. J. 1998, 4, 1351-1361.
3. (c) Bosman, A. W.; Jansen, H. M.; Meijer, E. W. Chem. Rev. 1999, 99, 1665-1688.
4. (d) Fischer, M.; Vögtle, F. Angew. Chem. 1999, 111, 934-955;
5. Angew. Chem., Int. Ed. 1999, 38, 884-905.
6. (e) Newkome, G. R.; Moorefield, C. N.; Vögtle F. Dendrimers and Dendrons. Concepts, Syntheses, Applications, Wiley-VCH: Weinheim, 2001.
7. (f) Grayson, S. M.; Fréchet, J. M. J. Chem. Rev. 2001, 101, 3819-3868.
8. (a) Fréchet, J. M. J.; Tomalia, D. A. Dendrimers and Other Dendritic Polymers; Wiley: New York, 2001.
9. (b) Gao, C.; Yan, D. Prog. Polym. Sci. 2004, 29, 183-275.
10. (a) Schlüter, A. D.; Rabe, J. P. Angew. Chem. 2000, 112, 860-880;
11. Angew. Chem., Int. Ed. 2000, 39, 864-883.
12. (b) Zhang, A. F.; Shu, L. J.; Bo, Z. S.; Schlüter, A. D. Macromol. Chem. Phys. 2003, 204, 328-339.
13. (c) Frauenrath, H. Prog. Polym. Sci. 2005, 30, 325-384.
14. For the concept of the repetitive (iterative) synthesis, see: (a) Buhleier, E.; Wehner, W.; Vögtle, F. Synthesis 1978, 155-158.
15. (b) Feuerbacher, N.; Vögtle, F. Top. Curr. Chem. 1998, 197, 2-18.
16. (a) Zimmerman, S. C.; Zeng, F.; Reichert, D. E. C.; Kolotuchin, S. V. Science 1996, 271, 1095-1098.
17. (b) Zeng, F. W.; Zimmerman, S. C. Chem. Rev. 1997, 97, 1681-1712.
18. (c) Ma, Y.; Kolotuchin, S. V.; Zimmerman, S. C. J. Am. Chem. Soc. 2002, 124, 13757-13769.
19. (d) Zeng, F. W.; Zimmerman, S. C.; Kolotuchin, S. V.; Reichert, D. E. C.; Ma, Y. G. Tetrahedron 2002, 58, 825-843.
20. (e) Gibson, H. W.; Yamaguchi, N.; Hamilton, L.; Jones, J. W. J. Am. Chem. Soc. 2002, 124, 4653-4665.
21. (f) Franz, A.; Bauer, W.; Hirsch, A. Angew. Chem., Int. Ed. 2005, 44, 1564-1567.
22. (g) Sun, H.; Kaifer, A. E. Org. Lett. 2005, 7, 3845-3848.
23. (h) Rudzevich, Y.; Rudzevich, V.; Moon, C; Schnell, I.; Fischer, K.; Böhmer, V. J. Am. Chem. Soc. 2005, 127, 14168-14169.
24. (i) Hahn, U.; González, J. J.; Huerta, E.; Segura, M.; Eckert, J.-F.; Cardinali, F.; De Mendoza, J.; Nierengarten, J.-F. Chem. Eur. J. 2005, 11, 6666-6672.
25. (a) Krause, W.; Hackmann-Schlichter, N.; Maier, F. K.; Müller, R. Top. Curr. Chem. 2000, 210, 261.
26. (b) Lee, C. C.; MacKay, J. A.; Fréchet, J. M. J.; Szoka, F. C. Nat. Biotechnol. 2005, 23, 1517-1526.
27. Dennig, J. Top. Curr. Chem. 2003, 228, 227-236.
28. (a) Hudson, S. D.; Jung, H.-T.; Percec, V.; Cho, W.-D.; Johansson, G.; Ungar, G.; Balagurusamy, V. S. K. Science 1997, 278, 449-452.
29. (b) Percec, V.; Ahn, C.-H.; Ungar, G.; Yeardley, D. J. P.; Möller, M.; Sheiko, S. Nature 1998, 391, 161-164.
30. (c) Percec, V.; Glodde, M.; Bera, T. K.; Miura, Y.; Shiyanovska, I.; Singer, K. D.; Balagurusamy, V. S. K.; Heiney, P. A.; Schnell, I.; Rapp, A.; Spiess, H.-W.; Hudson, S. D.; Duan, H. Nature 2002, 384-387.
31. (d) Percec, V.; Dulcey, A. E.; Balagurusamy, V. S. K.; Miura, Y.; Smidrkal, J.; Peterca, M.; Nummelin, S.; Edlung, U.; Hudson, S. D.; Heiney, P. A.; Duan, H.; Masonov, S. N.; Vinogradov. S. A. Nature 2004, 430, 764-768.
32. (e) Bottcher, C.; Schade, B.; Ecker, C.; Rabe, J. P.; Shu, L. J.; Schlüter, A. D. Chem. Eur. J. 2005, 11, 2923-2928.
33. (f) Chow, H.-F.; Zhang, J. Chem. Eur. J. 2005, 11, 5817-5831.
34. (g) Yan, D.; Zhou, Y.; Hou, J. Science 2004, 303, 65-67.
35. (a) Hawker, C. J.; Wooley, K. L.; Fréchet, J. M. J. J. Chem. Soc., Perkin Trans. 1 1993, 1287.
36. (b) Zhang, S.; Rio, Y.; Cardinali, F.; Bourgogne, C.; Gallani, J.-L.; Nierengarten, J.-F. J. Org. Chem. 2003, 68, 9787-9797.
37. (c) Percec, V.; Imam, M. R.; Bera, T. K.; Balagurusamy, V. S. K.; Peterca, M.; Heiney, P. A. Angew. Chem., Int. Ed. 2005, 117, 4817-4823.
38. (d) Wu, P.; Malkoch, M.; Hunt, J. N.; Vestberg, R.; Kaltgrad, E.; Finn, M. G.; Fokin, V. V.; Sharpless, K. B.; Hawker, C. J. Chem. Commun. 2005, 5775-5777.
39. (a) Newkome, G. R.; Weis, C. D.; Moorefield, C. N.; Baker, G. R.; Childs, B. J.; Epperson, J. Angew. Chem. 1998, 110, 318-321;
40. Angew. Chem., Int. Ed. 1998, 37, 307-310.
41. (b) Baker, J. R.; Quintana, A.; Piehler, L.; Banazak-Holl, M.; Tomalia, D.; Raczka, E. Biomed. Microdevices 2001, 3, 61-69.
42. For recent examples see: (a) Brouwer, A. J.; Liskamp, R. M. J. Eur. J. Org. Chem. 2005, 487-495.
43. (b) Saez, I. M.; Goodby, J. W. Chem. Commun. 2003, 1726-1727.
44. (c) Saez, I. M.; Goodby, J. W. Chem. Eur. J. 2003, 9, 4869-4877.
45. (d) Müller, S.; Schlüter, A. D. Chem. Eur. J. 2005, 11, 5589-5610.
46. (e) Ropponen, J.; Nummelin, S.; Rissanen, K. Org. Lett, 2004, 6, 2495-2497.
47. (f) Chow, H.-K.; Leung, C.-F.; Li, W.; Wong, K.-W.; Xi, L. Angew. Chem. 2003, 115, 5069-5073;
48. Angew. Chem., Int. Ed. 2003, 42, 4919-4923.
49. Steffensen, M. B.; Simanek, E. E. Angew. Chem., Int. Ed. 2004, 43, 5178-5180.
50. (a) Archut, A.; Gestermann, S.; Hesse, R.; Kaufmann. C.; Vögtle, F. Synlett 1998, 546-548.
51. (b) James, T. D.; Shimori, H.; Takeuchi, M.; Shinkai, S. J. Chem. Soc., Chem. Commun. 1996, 705-706.
52. (c) Ornelas, C.; Méry, D.; Blais, J.-C.; Cloutet, E.; Aranzaes, J. R.; Astruc, D. Angew. Chem., Int. Ed. 2005, 44, 7399-7404.
53. (a) Vögtle, F.; Fakhrnabavi, H.; Lukin, O. Org. Lett. 2004, 6, 1075-1078.
54. (b) Vögtle, F.; Fakhrnabavi, H.; Lukin, O.; Müller, S.; Friedhofen, J.; Schalley, C. A. Eur. J. Org. Chem. 2004, 4717-4724.
55. For pioneering work, see: (a) Hawker, C.; Fréchet, J. M. J. J. Chem. Soc., Chem. Commun. 1990, 1010.
56. (b) Hawker, C.; Fréchet, J. M. J. J. Am. Chem. Soc. 1990, 112, 7638.
57. (a) Newkome, G. R.; Moorefield, C. N.; Keith, J. M.; Baker, G. R.; Escamila, G. H. Angew. Chem., Int. Ed. 1994, 33, 666-668.
58. (b) Galliot, C.; Larré, C.; Caminade, A. M.; Majoral, J. P. Science 1997, 277, 1981.
59. (c) Larré, C.; Bressolles, D.; Turrin, C.; Donnadieu, B.; Caminade, A. M.; Majoral, J. P. J. Am. Chem. Soc. 1998, 120, 13070-13082.
60. (d) Sakamoto, J.; Müllen, K. Org. Lett. 2004, 6, 4277-4280.
61. (a) Maraval, V.; Laurent, R.; Donnadieu, B.; Mauzac, M.; Caminade, A. M.; Majoral, J. P. J. Am. Chem. Soc. 2000, 122, 2499-2511.
62. (b) Gilles, E. R.; Fréchet, J. M. J. J. Am. Chem. Soc. 2002, 124, 14137-14146.
63. The term "Janus" denoting two different faces of one entity is often used in dendrimer research. See for example refs 9c, 11b, and 11c.
64. (a) DeChristopher, P. J.; Adamek, J. P.; Lyon, G. D.; Klein, S. A.; Baumgarten, R. J. J. Org. Chem. 1974, 39, 3525-3532.
65. (b) Hutchins, R. O.; Cistone, F.; Goldsmith, B. Heuman, P. J. Org. Chem. 1975, 40, 2018-2020.
66. (a) Mekelburger, H.-B.; Rissanen, K.; Vögtle, F. Chem. Ber. 1993, 126, 1161-1169.
67. (b) Lambert, J. B.; Pflug, J. L.; Denari, J. M. Organometallics 1996, 15, 615-625.
68. (c) Kriesel, J. W.; König, S.; Freitas, M. A.; Marshall, A. G.; Leary, J. A.; Tilley, T. D. J. Am. Chem. Soc. 1998, 120, 12207-12215.
69. (d) Larré, C.; Bressolles, D.; Turrin, C.; Donnadieu, B.; Caminade, A. M.; Majoral, J. P. J. Am. Chem. Soc. 1998, 120, 13070-13082.
70. (e) Gossage, R. A.; Muñoz-Martinez, E.; Frey, H.; Burgath, A.; Lutz, M.; Spek, A. L.; van Koten, G. Chem. Eur. J. 1999, 5, 2191-2197.
71. (f) Nanjo, M.; Sunaga, T.; Sekiguchi, A.; Horn, E. Inorg. Chem. Commun. 1999, 2, 203-206.
72. (g) Ranganathan, D.; Kurur, S.; Gilardi, R.; Karle, I. L. Biopolymers 2000, 54, 289-295.
73. (h) Brewis, M.; Clarkson, G. J.; Helliwell, M.; Holder, A. M.; McKeown, N. B. Chem. Eur. J. 2000, 6, 4630-4636.
74. (i) Bauer, R. E.; Enkelmann, V.; Wiesler, U. M.; Berresheim, A. J.; Müllen, K. Chem. Eur. J. 2002, 8, 3858-3864.
75. (j) Portner, K.; Nieger, M.; Vögtle, F. Synlett 2004, 1167-1170.
76. (k) Harder, S.; Meijboom, R.; Moss, J. R. J. Oganomet Chem. 2004, 689, 1095-1101.
77. (l) Saalfrank, R. W.; Deutscher, C.; Maid, H.; Ako, A. M.; Sperner, S.; Nakajima, T.; Bauer, W.; Hampel, F.; Hess, B. A.; van Eikema Hommes, N. J. R.; Puchta, R.; Heinemann, F. W. Chem. Eur. J. 2004, 10, 1899-1905.
78. (m) Williams, A. A.; Day, B. S.; Kite, B. L.; McPherson, M. K.; Slebodnick, C. Morris, J. R.; Candour, R. D. Chem. Commun. 2005, 5053-5055.
79. (a) Seyferth, D.; Son, D. Y.; Rheingold, A. L.; Ostrander, R. L. Organometallics 1994, 13, 2682-2690.
80. (b) Rajca, A.; Janicki, S. J. Org. Chem. 1994, 59, 7099-7107.
81. (c) Sekiguchi, A.; Nanjo, M.; Kabuto, C.; Sakurai, H. J. Am. Chem. Soc. 1995, 117, 4195-4196.
82. (d) Karakaya, B.; Claussen, W.; Gessler, K.; Saenger, W.; Schlüter, A. D. J. Am. Chem. Soc. 1997, 119, 3296-3301.
83. (e) Brewis, M.; Clarkson, G. J.; Goddard, V.; Helliwell, M.; Holder, A. M.; McKeown, N. B. Angew. Chem. 1998, 110, 1185-1187;
84. Angew. Chem., Int. Ed. 1998, 37, 1092-1094.
85. For example: Polyakov, O. G.; Ivanova, S. M.; Gaudinski, C. M.; Miller, S. M.; Anderson, O. P.; Strauss, S. H. Organometallics 1999, 18, 3769-3771.
86. De Ridder, D. J. A.; Goubitz, K.; Fontijn, M.; Capkovà, P.; Dova, E.; Schenk, H. Acta Crystallogr. 2001, B57, 780-790.
87. ar-S-N-S, more than 10 carbon atoms of the molecule and all of the entrapped chloroform solvent could not be located from the electron density map. Attempts at growing better crystals of 23 are in progress.
88. (a) Felder, T.; Schalley, C. A.; Fakhrnabavi, H.; Lukin, O. Chem. Eur. J. 2005, 11, 5625-5636.
89. (b) Baytekin, B.; Werner, N.; Luppertz, F.; Engeser, M.; Brüggemann, J.; Bitter, S.; Henkel, R.; Felder, T.; Schalley, C. A. Int. J. Mass Spectrom. 2006, 249-250, 138-148.