A poly(para-phenylene) with hydrophobic and hydrophilic dendrons: Prototype of an amphiphilic cylinder with the potential to segregate lengthwise

Angewandte Chemie - International Edition

Volumn 38, Issue 16, 1999, Pages 2370-2372

  Bo, Zhishan ^a   Rabe, Jürgen P ^b   Schlüter, A Dieter ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

^b HUMBOLDT UNIVERSITY   (Germany)

Author keywords

Amphiphiles; Dendrimers; Monolayers; Nanostructures; Polymers

Indexed keywords

AMPHOPHILE; DENDRIMER; MEMBRANE PROTEIN; POLYMER;

ARTICLE; BROMINATION; CHEMICAL REACTION; COLUMN CHROMATOGRAPHY; ESTERIFICATION; HYDROPHILICITY; HYDROPHOBICITY; ION CHANNEL; MACROMOLECULE; NONHUMAN; OXIDATION; PURIFICATION; SYNTHESIS;

EID: 0033549791     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19990816)38:16<2370::AID-ANIE2370>3.0.CO;2-T     Document Type: Article

References (24)

1. G. R. Newkome, C. N. Moorefield, F. Vögtle, Dendritic Molecules. Concepts, Syntheses, Perspectives, VCH, Weinheim, 1996.
2. F. Zeng, S. C. Zimmerman, Chem. Rev. 1997, 97, 1681-1712; A. P. H. J. Schenning, C. Elissen-Roman, J.-W. Weener, M. W. P. L. Baars, S. J. van der Gaast, E. W. Meijer, J. Am. Chem. Soc. 1998, 120, 8199-8208, and references therein.
3. F. Zeng, S. C. Zimmerman, Chem. Rev. 1997, 97, 1681-1712; A. P. H. J. Schenning, C. Elissen-Roman, J.-W. Weener, M. W. P. L. Baars, S. J. van der Gaast, E. W. Meijer, J. Am. Chem. Soc. 1998, 120, 8199-8208, and references therein.
4. V. Percec, C. H. Ahn, G. Ungar, D. J. P. Yeardley, M. Möller, S. S. Sheiko, Nature 1998, 391, 161-164.
5. B. Karakaya, W. Claussen, K. Gessler, W. Saenger, A. D. Schlüter, J. Am. Chem. Soc. 1997, 119, 3296-3301; W. Stocker, B. Karakaya, B. L. Schürmann, J. P. Rabe, A. D. Schlüter, J. Am. Chem. Soc. 1998, 120, 7691-7695; "Dendrimers with Polymeric Cores: Towards Nanocylinders": A. D. Schlüter, Top. Curr. Chem. 1998, 197, 165-192; W. Stocker, B. L. Schürmann, J. P. Rabe, S. Förster, R. Lindner, I. Neubert, A. D. Schlüter, Adv. Mater. 1998, 10, 793-797. For a recent work on dendronized poly(phenylenevinylene)s, see Z. Bao, K. R. Amundson, A. J. Lovinger, Macromolecules 1998, 31, 8647-8649.
6. B. Karakaya, W. Claussen, K. Gessler, W. Saenger, A. D. Schlüter, J. Am. Chem. Soc. 1997, 119, 3296-3301; W. Stocker, B. Karakaya, B. L. Schürmann, J. P. Rabe, A. D. Schlüter, J. Am. Chem. Soc. 1998, 120, 7691-7695; "Dendrimers with Polymeric Cores: Towards Nanocylinders": A. D. Schlüter, Top. Curr. Chem. 1998, 197, 165-192; W. Stocker, B. L. Schürmann, J. P. Rabe, S. Förster, R. Lindner, I. Neubert, A. D. Schlüter, Adv. Mater. 1998, 10, 793-797. For a recent work on dendronized poly(phenylenevinylene)s, see Z. Bao, K. R. Amundson, A. J. Lovinger, Macromolecules 1998, 31, 8647-8649.
7. B. Karakaya, W. Claussen, K. Gessler, W. Saenger, A. D. Schlüter, J. Am. Chem. Soc. 1997, 119, 3296-3301; W. Stocker, B. Karakaya, B. L. Schürmann, J. P. Rabe, A. D. Schlüter, J. Am. Chem. Soc. 1998, 120, 7691-7695; "Dendrimers with Polymeric Cores: Towards Nanocylinders": A. D. Schlüter, Top. Curr. Chem. 1998, 197, 165-192; W. Stocker, B. L. Schürmann, J. P. Rabe, S. Förster, R. Lindner, I. Neubert, A. D. Schlüter, Adv. Mater. 1998, 10, 793-797. For a recent work on dendronized poly(phenylenevinylene)s, see Z. Bao, K. R. Amundson, A. J. Lovinger, Macromolecules 1998, 31, 8647-8649.
8. B. Karakaya, W. Claussen, K. Gessler, W. Saenger, A. D. Schlüter, J. Am. Chem. Soc. 1997, 119, 3296-3301; W. Stocker, B. Karakaya, B. L. Schürmann, J. P. Rabe, A. D. Schlüter, J. Am. Chem. Soc. 1998, 120, 7691-7695; "Dendrimers with Polymeric Cores: Towards Nanocylinders": A. D. Schlüter, Top. Curr. Chem. 1998, 197, 165-192; W. Stocker, B. L. Schürmann, J. P. Rabe, S. Förster, R. Lindner, I. Neubert, A. D. Schlüter, Adv. Mater. 1998, 10, 793-797. For a recent work on dendronized poly(phenylenevinylene)s, see Z. Bao, K. R. Amundson, A. J. Lovinger, Macromolecules 1998, 31, 8647-8649.
9. B. Karakaya, W. Claussen, K. Gessler, W. Saenger, A. D. Schlüter, J. Am. Chem. Soc. 1997, 119, 3296-3301; W. Stocker, B. Karakaya, B. L. Schürmann, J. P. Rabe, A. D. Schlüter, J. Am. Chem. Soc. 1998, 120, 7691-7695; "Dendrimers with Polymeric Cores: Towards Nanocylinders": A. D. Schlüter, Top. Curr. Chem. 1998, 197, 165-192; W. Stocker, B. L. Schürmann, J. P. Rabe, S. Förster, R. Lindner, I. Neubert, A. D. Schlüter, Adv. Mater. 1998, 10, 793-797. For a recent work on dendronized poly(phenylenevinylene)s, see Z. Bao, K. R. Amundson, A. J. Lovinger, Macromolecules 1998, 31, 8647-8649.
10. N. Voyer, J. Lamothe, Tetrahedron 1995, 51, 9241; N. Voyer, M. Robitaille, J. Am. Chem. Soc. 1995, 117, 6599-6600.
11. N. Voyer, J. Lamothe, Tetrahedron 1995, 51, 9241; N. Voyer, M. Robitaille, J. Am. Chem. Soc. 1995, 117, 6599-6600.
12. "Molecular Assemblies and Membranes": J.-H. Fuhrhop, J. Köning in Supramolecular Chemistry (Ed.: J. F. Stoddart), Royal Society of Chemistry, London, 1994.
13. W. Marzin, J. Prakt. Chem. 1933, 138, 103-110; L. Lamba, J. S. Jaydeep, J. Tour, J. Am. Chem. Soc. 1994, 116, 11723-11736.
14. W. Marzin, J. Prakt. Chem. 1933, 138, 103-110; L. Lamba, J. S. Jaydeep, J. Tour, J. Am. Chem. Soc. 1994, 116, 11723-11736.
15. Traces of the dioxidation product can be removed by column chromatography. This, however, was not normally done and the raw material was used in the next step.
16. J. M. J. Fréchet, K. L. Wooley, C. J. Hawker, J. Am. Chem. Soc. 1991, 113, 4252-4261.
17. 4 because this leads to undesired debromination.
18. U. Lauter, W. H. Meyer, G. Wegner, Macromolecules 1997, 30, 209-2101.
19. J. Frahn, B. Karakaya, A. Schäfer, A. D. Schlüter, Tetrahedron 1997, 53, 15459-15467.
20. S. Förster, I. Neubert, A. D. Schlüter, P. Lindner, Macromolecules, in press.
21. n < 40. This range has to be considered with some care because of partial signal overlap.
22. A. I. Kitaigovodstry, Mixed Crystals, Springer Series in Solid-State Sciences 33, Springer, Berlin, 1984, p. 353.
23. Z. Bo, A. D. Schlüter, unpublished results.
24. For the behavior of a polythiophene with ethyleneoxy and alkyl chains at the air/water interface, see T. Bjornholm, D. R. Greve, N. Reitzel, T. Hassenkam, K. Kjaer, P. B. Howes, N. B. Larsen, J. Bogelund, M. Jayaraman, P. C. Ewbank, R. D. McCullough, J. Am. Chem. Soc. 1998, 120, 7643-7644.