Helical superstructures from charged poly(styrene)- poly(isocyanodipeptide) block copolymers

Science

Volumn 280, Issue 5368, 1998, Pages 1427-1430

  Cornelissen, Jeroen J L M ^a   Fischer, Matthias ^a   Sommerdijk, Nico A J M ^a   Nolte, Roeland J M ^a  

^a RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ISOCYANIC ACID DERIVATIVE; POLYSTYRENE;

ARTICLE; CHIRALITY; CYTOARCHITECTURE; MACROMOLECULE; MEMBRANE VESICLE; MICELLE; PRIORITY JOURNAL; STRUCTURE ANALYSIS;

EID: 0032577361     PISSN: 00368075     EISSN: None     Source Type: Journal    
DOI: 10.1126/science.280.5368.1427     Document Type: Article

References (41)

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4. Phospholipid-derived surfactants: J. M. Schnur, ibid. 262, 1669 (1993), and references therein; N. A. J. M. Sommerdijk et al., J. Chem. Soc. Chem. Commun. 1994, 1941 (1994); N. A. J. M. Sommerdijk, M. H. L. Lambermon, M. C. Feiters, R. J. M. Nolte, B. Zwanenburg, Chem. Commun. 1997, 1423 (1997). Amino acid-derived surfactants: N. Nakashima, S. Asakuma, T. Kunitake, J. Am. Chem. Soc. 107, 509 (1985); T. Kunitake and N. Yamada, J. Chem. Soc. Chem. Commun. 1986, 655 (1986); T. Kunitake, J.-M. Kim, Y. Ishikawa, J. Chem. Soc. Perkin Trans. 2, 885 (1991) ; N. A. J. M. Sommerdijk, M. H. L. Lambermon, M. C. Feiters, R. J. M. Nolte, B. Zwanenburg, Chem. Commun. 1997, 455 (1997). Nucleic acid-derived surfactants: H. Yanagawa, Y. Ogawa, H. Furuta, K. Tsuno, Chem. Lett. 1988, 269 (1988); J. Am. Chem. Soc. 114, 3414 (1989). Sugar-derived surfactants: J. H. Fuhrhop and W. Helfrich, Chem. Rev. 93, 1565 (1993), and references therein; R. J. H. Hafkamp, M. C. Feiters, R. J. M. Nolte, Angew. Chem. 106, 1054 (1994).
5. Phospholipid-derived surfactants: J. M. Schnur, ibid. 262, 1669 (1993), and references therein; N. A. J. M. Sommerdijk et al., J. Chem. Soc. Chem. Commun. 1994, 1941 (1994); N. A. J. M. Sommerdijk, M. H. L. Lambermon, M. C. Feiters, R. J. M. Nolte, B. Zwanenburg, Chem. Commun. 1997, 1423 (1997). Amino acid-derived surfactants: N. Nakashima, S. Asakuma, T. Kunitake, J. Am. Chem. Soc. 107, 509 (1985); T. Kunitake and N. Yamada, J. Chem. Soc. Chem. Commun. 1986, 655 (1986); T. Kunitake, J.-M. Kim, Y. Ishikawa, J. Chem. Soc. Perkin Trans. 2, 885 (1991) ; N. A. J. M. Sommerdijk, M. H. L. Lambermon, M. C. Feiters, R. J. M. Nolte, B. Zwanenburg, Chem. Commun. 1997, 455 (1997). Nucleic acid-derived surfactants: H. Yanagawa, Y. Ogawa, H. Furuta, K. Tsuno, Chem. Lett. 1988, 269 (1988); J. Am. Chem. Soc. 114, 3414 (1989). Sugar-derived surfactants: J. H. Fuhrhop and W. Helfrich, Chem. Rev. 93, 1565 (1993), and references therein; R. J. H. Hafkamp, M. C. Feiters, R. J. M. Nolte, Angew. Chem. 106, 1054 (1994).
6. Phospholipid-derived surfactants: J. M. Schnur, ibid. 262, 1669 (1993), and references therein; N. A. J. M. Sommerdijk et al., J. Chem. Soc. Chem. Commun. 1994, 1941 (1994); N. A. J. M. Sommerdijk, M. H. L. Lambermon, M. C. Feiters, R. J. M. Nolte, B. Zwanenburg, Chem. Commun. 1997, 1423 (1997). Amino acid-derived surfactants: N. Nakashima, S. Asakuma, T. Kunitake, J. Am. Chem. Soc. 107, 509 (1985); T. Kunitake and N. Yamada, J. Chem. Soc. Chem. Commun. 1986, 655 (1986); T. Kunitake, J.-M. Kim, Y. Ishikawa, J. Chem. Soc. Perkin Trans. 2, 885 (1991) ; N. A. J. M. Sommerdijk, M. H. L. Lambermon, M. C. Feiters, R. J. M. Nolte, B. Zwanenburg, Chem. Commun. 1997, 455 (1997). Nucleic acid-derived surfactants: H. Yanagawa, Y. Ogawa, H. Furuta, K. Tsuno, Chem. Lett. 1988, 269 (1988); J. Am. Chem. Soc. 114, 3414 (1989). Sugar-derived surfactants: J. H. Fuhrhop and W. Helfrich, Chem. Rev. 93, 1565 (1993), and references therein; R. J. H. Hafkamp, M. C. Feiters, R. J. M. Nolte, Angew. Chem. 106, 1054 (1994).
7. Phospholipid-derived surfactants: J. M. Schnur, ibid. 262, 1669 (1993), and references therein; N. A. J. M. Sommerdijk et al., J. Chem. Soc. Chem. Commun. 1994, 1941 (1994); N. A. J. M. Sommerdijk, M. H. L. Lambermon, M. C. Feiters, R. J. M. Nolte, B. Zwanenburg, Chem. Commun. 1997, 1423 (1997). Amino acid-derived surfactants: N. Nakashima, S. Asakuma, T. Kunitake, J. Am. Chem. Soc. 107, 509 (1985); T. Kunitake and N. Yamada, J. Chem. Soc. Chem. Commun. 1986, 655 (1986); T. Kunitake, J.-M. Kim, Y. Ishikawa, J. Chem. Soc. Perkin Trans. 2, 885 (1991) ; N. A. J. M. Sommerdijk, M. H. L. Lambermon, M. C. Feiters, R. J. M. Nolte, B. Zwanenburg, Chem. Commun. 1997, 455 (1997). Nucleic acid-derived surfactants: H. Yanagawa, Y. Ogawa, H. Furuta, K. Tsuno, Chem. Lett. 1988, 269 (1988); J. Am. Chem. Soc. 114, 3414 (1989). Sugar-derived surfactants: J. H. Fuhrhop and W. Helfrich, Chem. Rev. 93, 1565 (1993), and references therein; R. J. H. Hafkamp, M. C. Feiters, R. J. M. Nolte, Angew. Chem. 106, 1054 (1994).
8. Phospholipid-derived surfactants: J. M. Schnur, ibid. 262, 1669 (1993), and references therein; N. A. J. M. Sommerdijk et al., J. Chem. Soc. Chem. Commun. 1994, 1941 (1994); N. A. J. M. Sommerdijk, M. H. L. Lambermon, M. C. Feiters, R. J. M. Nolte, B. Zwanenburg, Chem. Commun. 1997, 1423 (1997). Amino acid-derived surfactants: N. Nakashima, S. Asakuma, T. Kunitake, J. Am. Chem. Soc. 107, 509 (1985); T. Kunitake and N. Yamada, J. Chem. Soc. Chem. Commun. 1986, 655 (1986); T. Kunitake, J.-M. Kim, Y. Ishikawa, J. Chem. Soc. Perkin Trans. 2, 885 (1991) ; N. A. J. M. Sommerdijk, M. H. L. Lambermon, M. C. Feiters, R. J. M. Nolte, B. Zwanenburg, Chem. Commun. 1997, 455 (1997). Nucleic acid-derived surfactants: H. Yanagawa, Y. Ogawa, H. Furuta, K. Tsuno, Chem. Lett. 1988, 269 (1988); J. Am. Chem. Soc. 114, 3414 (1989). Sugar-derived surfactants: J. H. Fuhrhop and W. Helfrich, Chem. Rev. 93, 1565 (1993), and references therein; R. J. H. Hafkamp, M. C. Feiters, R. J. M. Nolte, Angew. Chem. 106, 1054 (1994).
9. Phospholipid-derived surfactants: J. M. Schnur, ibid. 262, 1669 (1993), and references therein; N. A. J. M. Sommerdijk et al., J. Chem. Soc. Chem. Commun. 1994, 1941 (1994); N. A. J. M. Sommerdijk, M. H. L. Lambermon, M. C. Feiters, R. J. M. Nolte, B. Zwanenburg, Chem. Commun. 1997, 1423 (1997). Amino acid-derived surfactants: N. Nakashima, S. Asakuma, T. Kunitake, J. Am. Chem. Soc. 107, 509 (1985); T. Kunitake and N. Yamada, J. Chem. Soc. Chem. Commun. 1986, 655 (1986); T. Kunitake, J.-M. Kim, Y. Ishikawa, J. Chem. Soc. Perkin Trans. 2, 885 (1991) ; N. A. J. M. Sommerdijk, M. H. L. Lambermon, M. C. Feiters, R. J. M. Nolte, B. Zwanenburg, Chem. Commun. 1997, 455 (1997). Nucleic acid-derived surfactants: H. Yanagawa, Y. Ogawa, H. Furuta, K. Tsuno, Chem. Lett. 1988, 269 (1988); J. Am. Chem. Soc. 114, 3414 (1989). Sugar-derived surfactants: J. H. Fuhrhop and W. Helfrich, Chem. Rev. 93, 1565 (1993), and references therein; R. J. H. Hafkamp, M. C. Feiters, R. J. M. Nolte, Angew. Chem. 106, 1054 (1994).
10. Phospholipid-derived surfactants: J. M. Schnur, ibid. 262, 1669 (1993), and references therein; N. A. J. M. Sommerdijk et al., J. Chem. Soc. Chem. Commun. 1994, 1941 (1994); N. A. J. M. Sommerdijk, M. H. L. Lambermon, M. C. Feiters, R. J. M. Nolte, B. Zwanenburg, Chem. Commun. 1997, 1423 (1997). Amino acid-derived surfactants: N. Nakashima, S. Asakuma, T. Kunitake, J. Am. Chem. Soc. 107, 509 (1985); T. Kunitake and N. Yamada, J. Chem. Soc. Chem. Commun. 1986, 655 (1986); T. Kunitake, J.-M. Kim, Y. Ishikawa, J. Chem. Soc. Perkin Trans. 2, 885 (1991) ; N. A. J. M. Sommerdijk, M. H. L. Lambermon, M. C. Feiters, R. J. M. Nolte, B. Zwanenburg, Chem. Commun. 1997, 455 (1997). Nucleic acid-derived surfactants: H. Yanagawa, Y. Ogawa, H. Furuta, K. Tsuno, Chem. Lett. 1988, 269 (1988); J. Am. Chem. Soc. 114, 3414 (1989). Sugar-derived surfactants: J. H. Fuhrhop and W. Helfrich, Chem. Rev. 93, 1565 (1993), and references therein; R. J. H. Hafkamp, M. C. Feiters, R. J. M. Nolte, Angew. Chem. 106, 1054 (1994).
11. Phospholipid-derived surfactants: J. M. Schnur, ibid. 262, 1669 (1993), and references therein; N. A. J. M. Sommerdijk et al., J. Chem. Soc. Chem. Commun. 1994, 1941 (1994); N. A. J. M. Sommerdijk, M. H. L. Lambermon, M. C. Feiters, R. J. M. Nolte, B. Zwanenburg, Chem. Commun. 1997, 1423 (1997). Amino acid-derived surfactants: N. Nakashima, S. Asakuma, T. Kunitake, J. Am. Chem. Soc. 107, 509 (1985); T. Kunitake and N. Yamada, J. Chem. Soc. Chem. Commun. 1986, 655 (1986); T. Kunitake, J.-M. Kim, Y. Ishikawa, J. Chem. Soc. Perkin Trans. 2, 885 (1991) ; N. A. J. M. Sommerdijk, M. H. L. Lambermon, M. C. Feiters, R. J. M. Nolte, B. Zwanenburg, Chem. Commun. 1997, 455 (1997). Nucleic acid-derived surfactants: H. Yanagawa, Y. Ogawa, H. Furuta, K. Tsuno, Chem. Lett. 1988, 269 (1988); J. Am. Chem. Soc. 114, 3414 (1989). Sugar-derived surfactants: J. H. Fuhrhop and W. Helfrich, Chem. Rev. 93, 1565 (1993), and references therein; R. J. H. Hafkamp, M. C. Feiters, R. J. M. Nolte, Angew. Chem. 106, 1054 (1994).
12. Phospholipid-derived surfactants: J. M. Schnur, ibid. 262, 1669 (1993), and references therein; N. A. J. M. Sommerdijk et al., J. Chem. Soc. Chem. Commun. 1994, 1941 (1994); N. A. J. M. Sommerdijk, M. H. L. Lambermon, M. C. Feiters, R. J. M. Nolte, B. Zwanenburg, Chem. Commun. 1997, 1423 (1997). Amino acid-derived surfactants: N. Nakashima, S. Asakuma, T. Kunitake, J. Am. Chem. Soc. 107, 509 (1985); T. Kunitake and N. Yamada, J. Chem. Soc. Chem. Commun. 1986, 655 (1986); T. Kunitake, J.-M. Kim, Y. Ishikawa, J. Chem. Soc. Perkin Trans. 2, 885 (1991) ; N. A. J. M. Sommerdijk, M. H. L. Lambermon, M. C. Feiters, R. J. M. Nolte, B. Zwanenburg, Chem. Commun. 1997, 455 (1997). Nucleic acid-derived surfactants: H. Yanagawa, Y. Ogawa, H. Furuta, K. Tsuno, Chem. Lett. 1988, 269 (1988); J. Am. Chem. Soc. 114, 3414 (1989). Sugar-derived surfactants: J. H. Fuhrhop and W. Helfrich, Chem. Rev. 93, 1565 (1993), and references therein; R. J. H. Hafkamp, M. C. Feiters, R. J. M. Nolte, Angew. Chem. 106, 1054 (1994).
13. Phospholipid-derived surfactants: J. M. Schnur, ibid. 262, 1669 (1993), and references therein; N. A. J. M. Sommerdijk et al., J. Chem. Soc. Chem. Commun. 1994, 1941 (1994); N. A. J. M. Sommerdijk, M. H. L. Lambermon, M. C. Feiters, R. J. M. Nolte, B. Zwanenburg, Chem. Commun. 1997, 1423 (1997). Amino acid-derived surfactants: N. Nakashima, S. Asakuma, T. Kunitake, J. Am. Chem. Soc. 107, 509 (1985); T. Kunitake and N. Yamada, J. Chem. Soc. Chem. Commun. 1986, 655 (1986); T. Kunitake, J.-M. Kim, Y. Ishikawa, J. Chem. Soc. Perkin Trans. 2, 885 (1991) ; N. A. J. M. Sommerdijk, M. H. L. Lambermon, M. C. Feiters, R. J. M. Nolte, B. Zwanenburg, Chem. Commun. 1997, 455 (1997). Nucleic acid-derived surfactants: H. Yanagawa, Y. Ogawa, H. Furuta, K. Tsuno, Chem. Lett. 1988, 269 (1988); J. Am. Chem. Soc. 114, 3414 (1989). Sugar-derived surfactants: J. H. Fuhrhop and W. Helfrich, Chem. Rev. 93, 1565 (1993), and references therein; R. J. H. Hafkamp, M. C. Feiters, R. J. M. Nolte, Angew. Chem. 106, 1054 (1994).
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20. For a discussion of other, nonhelical structures, see (8) and (9).
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23. The N-formyl-protected dipeptides were prepared according to standard protecting and coupling procedures and were converted into the isocyanides by a method developed by I. Ugi and R. Meyr [Angew. Chem. 70, 702 (1958)]. The optical purity could easily be checked by proton NMR spectroscopy, because racemization results in diastereomers with different chemical shifts. Detailed syntheses and physical characterization will be published elsewhere.
24. 2O-MeOH (1/1, v/v).
25. 3, C 0.05).
26. 3, C 0.05).
27. CHARMm Version 3.0, Revision 92.0911 (Residents and Fellows of Harvard College, Cambridge, MA, 1984, 1992).
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29. The spectroscopic data obtained for 1 perfectly matched the data of Ni(II) carbene complexes previously described (11).
30. Amine functionalized poly(styrene) was prepared as reported by J. C. M. van Hest et al. [Chem. Eur. J. 12, 1616 (1996)].
31. R. W. Stephany and W. Drenth, Recl. Trav. Chim. Pays-Bas 91, 1453 (1972).
32. -1.
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34. TEM was performed on a Philips EM210 microscope at an acceleration voltage of 60 kV. For AFM, a Nanoscope III instrument from Digital Instruments was used, operating in the tapping mode.
35. Samples were deposited from the aqueous dispersions onto copper grids coated with a thin film of polyvinyl formaldehyde plastic. Water was evaporated during a period of 1 to 10 min at atmospheric pressure. The remaining water was drained off, and the grids were shadowed with platinum at an angle of 45°.
36. A similar zigzag pattern has been observed in films of block copolymers of poly(hexyl isocyanate) and poly-(styrene) [J. T. Chen, E. L. Thomas, C. K. Ober, G.-P. Mao, Science 273, 343 (1996)].
37. V. N. Malashkevich, R. A. Kammerer, V. P. Efimov, T. Schulthess, J. Engel, ibid. 274, 761 (1996).
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40. M. Kauranen et al., ibid. 270, 966 1995).
41. We thank the Department of Macromolecular and Organic Chemistry (E. W. Meijer) of the Technical University Eindhoven for kindly providing some poly(styrene) samples, P. C. J. Kamer for useful suggestions, A. E. Rowan for the molecular modeling studies, M. M. Green for fruitful discussions, J. Gerritsen for the AFM measurements, and H. P. M. Geurts for help with the TEM. Supported by the Netherlands Foundation for Chemical Research with financial aid from the Netherlands Organization for Scientific Research.