Transformation of a spherical supramolecular dendrimer into a pyramidal columnar supramolecular dendrimer mediated by the fluorophobic effect

Angewandte Chemie - International Edition

Volumn 42, Issue 36, 2003, Pages 4338-4342

  Percec, Virgil ^a   Glodde, Martin ^a   Johansson, Gary ^a   Balagurusamy, Venkatachalapathy S K ^a   Heinev, Paul A ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

Dendrimers; Fluorophobic effect; Liquid crystals; Self assembly

Indexed keywords

SELF ASSEMBLY; SUPRAMOLECULAR CHEMISTRY;

SUPRAMOLECULAR DENDRIMERS;

DENDRIMERS;

AMPHOPHILE; DENDRIMER; DODECANE; N DODECAN 1 YLOXY DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CONFORMATIONAL TRANSITION; FLUORINATION; HYDROGENATION; LIQUID CRYSTAL; REACTION ANALYSIS; STRUCTURE ANALYSIS; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS; TECHNIQUE; THERMOSTABILITY;

EID: 0141996278     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200351804     Document Type: Article

References (47)

1. For selected reviews on fluorous phases in organic synthesis, see a) I. T. Horváth, Acc. Chem. Res. 1998, 31, 641
2. b) D. P. Curran, Angew. Chem. 1998, 110, 1230; Angew. Chem. Int. Ed. 1998, 37, 1174; Erratum: D. P. Curran, Angew. Chem. 1998, 110, 2569; Angew. Chem. Int. Ed. 1998, 37, 2292
3. b) D. P. Curran, Angew. Chem. 1998, 110, 1230; Angew. Chem. Int. Ed. 1998, 37, 1174; Erratum: D. P. Curran, Angew. Chem. 1998, 110, 2569; Angew. Chem. Int. Ed. 1998, 37, 2292
4. b) D. P. Curran, Angew. Chem. 1998, 110, 1230; Angew. Chem. Int. Ed. 1998, 37, 1174; Erratum: D. P. Curran, Angew. Chem. 1998, 110, 2569; Angew. Chem. Int. Ed. 1998, 37, 2292
5. b) D. P. Curran, Angew. Chem. 1998, 110, 1230; Angew. Chem. Int. Ed. 1998, 37, 1174; Erratum: D. P. Curran, Angew. Chem. 1998, 110, 2569; Angew. Chem. Int. Ed. 1998, 37, 2292
6. c) L. P. Barthel-Rosa, J. A. Gladysz, Coord. Chem. Rev. 1999, 190-192, 587
7. d) E. de Wolf, G. van Koten, B.-J. Deelman, Chem. Soc. Rev. 1999, 28, 37
8. e) C. Tschierscke, C. Markert, W. Bannwarth, S. Roller, A. Hebel, R. Haag, Angew. Chem. 2002, 114, 4136; Angew. Chem. Int. Ed. 2002, 41, 3964
9. e) C. Tschierscke, C. Markert, W. Bannwarth, S. Roller, A. Hebel, R. Haag, Angew. Chem. 2002, 114, 4136; Angew. Chem. Int. Ed. 2002, 41, 3964
10. f) J. A. Gladysz, D. P. Curran, Tetrahedron 2002, 58, 3823 (and papers published in this special issue).
11. For selected examples of publications on fluorinated molecules in self-assembly, see a) V. Percec, G. Johansson, G. Ungar, J. Zhou, J. Am. Chem. Soc. 1996, 118, 9855
12. b) S. D. Hudson, H.-T. Jung, V. Percec, W.-D. Cho, G. Johansson, G. Ungar, V. S. K. Balagurusamy, Science 1997, 278, 449;
13. c) G. W. Coates, A. R. Dunn, L. M. Henling, D. A. Dougherty, R. H. Grubbs, Angew. Chem. 1997, 109, 290; Angew. Chem. Int, Ed. Engl. 1997, 36, 248;
14. c) G. W. Coates, A. R. Dunn, L. M. Henling, D. A. Dougherty, R. H. Grubbs, Angew. Chem. 1997, 109, 290; Angew. Chem. Int, Ed. Engl. 1997, 36, 248;
15. d) W. J. Feast, P. W. Lövenich, H. Puschmann, C. Taliani, Chem. Commun. 2001, 505
16. e) V Percec, M. Glodde, T. K. Bera, Y. Miura, I. Shiyanovskaya, K. D. Singer, V. S. K. Balagurusamy, P. A. Heiney, I. Schnell, A. Rapp, H.-W. Spiess, S. D. Hudson, H. Duan, Nature 2002, 419, 384.
17. For selected examples of publications on fluorinated compounds in self-organization, see a) U. Dahn, C. Erdelen, H. Ringsdorf, R. Festag, J. H. Wendorff, P. A. Heiney, N. C. Maliszewskyj, Liq. Cryst. 1995, 19, 759;
18. b) G. Johansson, V. Percec, G. Ungar, K. Smith, Chem. Mater. 1997, 9, 164
19. c) V. Percec, D. Schlueter, G. Ungar, Macromolecules 1997, 30, 645
20. d) F. Guittard, E. T. de Givenchy, S. Geribaldi, A. Cambon, J. Fluorine Chem. 1999, 100, 85
21. e) X. H. Cheng, S. Diele, C. Tschierske, Angew. Chem. 2000, 112, 605; Angew. Chem. Int. Ed. 2000, 39, 592
22. e) X. H. Cheng, S. Diele, C. Tschierske, Angew. Chem. 2000, 112, 605; Angew. Chem. Int. Ed. 2000, 39, 592
23. f) C. Rocaboy, F. Hampel, J. A. Gladysz, J. Org. Chem. 2002, 67, 6863.
24. For several examples of fluorine in biomolecular and macro-molecular chemistry, see a) B. E. Smart in Organofluorine Chemistry. Principles and Commercial Applications (Eds.: R, E. Banks, B. E. Stuart, J. C. Tatlow), Plenum, New York, 1994; 12, 4015.
25. b) Modern Fluoropolymers (Ed.: J. Scheirs), Wiley, New York, 1997;
26. c) V. Percec, D. Schlueter, Y. K. Kwon, J. Blackwell, M. Möller, P. J. Slangen, Macromolecules 1995, 28, 8807;
27. d) G. Johansson, V. Percec, G. Ungar, J. Zhou, Macromolecules 1996, 29, 646;
28. e) Y Tang, G. Ghirlanda, N. Vaidehi, J. Kua, D. T. Mainz, W. A. Goddard III, W. F. DeGrado, D. A. Tirrel, Bio-chemistry 2001, 40, 2790
29. f) S. Sheiko, E. Lermann, M. Möller, Langmuir 1996, 12, 4015.
30. V. S. K. Balagurusamy, G. Ungar, V. Percec, G. Johansson, J. Am. Chem. Soc. 1997, 119, 1539.
31. V. Percec, W.-D. Cho, G. Ungar, D. J. P. Yeardley, J. Am. Chem. Soc. 2001, 123, 1302, and references therein.
32. a) V. Percec, M. N. Holerca, S. Uchida, W.-D. Cho, G. Ungar, Y. Lee, D. J. P. Yeardley, Chem. Eur. J. 2002, 8, 1106;
33. b) V. Percec, W.-D. Cho, G. Ungar, D. J. P. Yeardley, Chem. Eur. J. 2002, 8, 2011;
34. c) V. Percec, W.-D. Cho, P. E. Mosier, G, Ungar, D. J. P. Yeardley, J. Am. Chem. Soc. 1998, 120, 11061;
35. d) V. Percec, C.-H. Ahn, G. Ungar, D. J. P. Yeardley, M, Möller, S. S. Sheiko, Nature 1998, 391, 161.
36. a) D. J. P. Yeardley, G. Ungar, V. Percec, M. N. Holerca, G. Johansson, J. Am. Chem. Soc. 2000, 122, 1684;
37. b) H. Duan, S. D. Hudson, G. Ungar, M. N. Holerca, V. Percee, Chem. Eur. J. 2001, 7, 4134.
38. G. Ungar, Y. Liu, X. Zeng, V. Percec, W.-D. Cho, Science 2003, 299, 1208.
39. a) H. Zimmermann, R. Poupko, Z, Luz, J. Billard, Z. Naturforsch. A 1985, 40a, 149;
40. b) J. Malthête, A. Collet, Nouv. J. Chim. 1985, 9, 15;
41. c) A. M. Levelut, J. Malthête, A. Collet, J. Phys, 1986, 47, 351;
42. d) J. Malthête, A. Collet, J. Am. Chem. Soc. 1987, 109, 7544;
43. e) R. Poupko, Z. Luz, N. Spielberg, H. Zimmermann, J. Am. Chem. Soc. 1989,111, 6094;
44. f) H. Zimmemlann, V. V Bader, R. Poupko, E. J. Wachtel, Z. Luz, J. Am. Chem. Soc. 2002, 124, 15286.
45. Y. K. Kwon, S. Chvalun, A. I. Schneider, J. Blackwell, V. Percec, J. A. Heck, Macromolecules 1994, 27, 6129.
46. G. Ungar, D. Abramic, V. Percec, J. A. Heck, Liq. Cryst. 1996, 21, 73.
47. V. Percec, D, Schlueter, G. Ungar, S. Z. D. Cheng, A. Zhang, Macromolecules 1998, 31, 1745.