Expression of supramolecular chirality in aggregates of chiral amide-containing surfactants

Chemistry - A European Journal

Volumn 4, Issue 1, 1998, Pages 127-136

  Sommerdijk, N A J M ^a   Buynsters, P J J A ^a   Akdemir, H ^a   Geurts, D G ^a   Pistorius, A M A ^b   Feiters, M C ^a   Nolte, R J M ^a   Zwanenburg, B ^a  

^a RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

^b RADBOUD UNIVERSITY MEDICAL CENTER   (Netherlands)

Author keywords

Aggregations; Chirality; Helical structures; Hydrogen bonds; Supramolecular chemistry; Surfactants

Indexed keywords

EID: 0031887450     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3765(199801)4:1<127::aid-chem127>3.3.co;2-y     Document Type: Article

References (59)

1. J. H. Fuhrhop, W. Helfrich, Chem. Rev. 1993, 95, 1565-1582, and references therein.
2. a) K. Yamada, H. Ihara, T. Ide, T. Fukumoto, C. Hirayama, Chem. Lett. 1984, 1713-1716;
3. b) I. Sakurai, T. Karvamura, A. Dakurai, A. Kegami, T. Setoi, Mol. Cryst. Liq. Cryst. 1985, 130, 203-222;
4. c) N. Nakashima, S. Asakuma, T. Kunitake, J. Am. Chem. Soc. 1985, 107, 509-510;
5. d) T. Kunitake, N. Yamada, J. Chem. Soc. Chem. Commun. 1986, 655-656;
6. e) T. Kunitake, J.-M. Kim, Y. Ishikawa, J. Chem. Soc. Perkin Trans. 2, 1991, 885-890;
7. f) T. Imae, Y. Takahashi, H. Muramatsu, J. Am. Chem. Soc. 1992, 114, 3414-3415.
8. a) H. Yanagawa, Y. Ogawa, H. Furuta, K. Tsuno, Chem. Lett. 1988, 269-272;
9. b) H. Yanagawa, Y. Ogawa, H. Furuta, K. Tsuno, J. Am. Chem. Soc. 1989, 111, 4567-4570.
10. a) D. G. Rodes, S. L. Blechner, P. Yager, P. E. Schoen, Chem. Phys. Lipids 1988, 49, 39;
11. b) J. M. Schnur, Science 1993, 262, 1669-1676, and references therein.
12. a) T. A. A. Fonteijn, D. Hoekstra, J. B. F. N. Engberts, Langmuir 1992, 8, 2437;
13. b) F. Giulieri, M. P. Krafft, Angew. Chem. 1994, 106, 1583; Angew. Chem. Int. Ed. Engl. 1994, 33, 1514;
14. b) F. Giulieri, M. P. Krafft, Angew. Chem. 1994, 106, 1583; Angew. Chem. Int. Ed. Engl. 1994, 33, 1514;
15. c) J. G. Riess, F. Giulieri, F. Guillod, J. Greiner, M. P. Krafft, J. G. Riess, Chem. Eur. J. 1996, 2, 1335.
16. a) J.-H. Fuhrhop, P. Schnieder, E. Boekema, J. Am. Chem. Soc. 1988, 110, 2861-2867;
17. b) J.-H. Fuhrhop, S. Svenson, C. Boettcher, E. Rössler, H. M. Vieth, J. Am. Chem. Soc. 1990, 112, 4307-4312;
18. c) X. Lu, Z. Zhang, Y. Liang, J. Chem. Soc. Chem. Commun. 1994, 2731-2732;
19. d) J. M. Schnur, B. R. Ratna, J. V. Selinger, A. Singh, G. Jyothi, K. R. K. Easwaran, Science 1994, 264, 945.
20. a) T. C. Lubensky, J. Prost, J. Phys. II 1992, 2, 371;
21. b) W. Helfrich, J. Prost, Phys. Rev. A 1988, 38, 3065;
22. c) P. Nelson, T. Powers, Phys. Rev. Lett. 1992, 69, 2409;
23. d)M. S. Spector, K. R. K. Easwaran, G. Jyothi, J. V. Selinger, A. Singh, L. M. Schnur, Phys. Rev. E 1996, 53, 3804-3818.
24. J. M. Boggs, Biochim. Biophys. Acta 1987, 906, 353.
25. D. A. Frankel, D. F. O'Brien, J. Am. Chem. Soc. 1994, 116, 10057-10069.
26. a) N. A. J. M. Sommerdijk, P. J. J. A. Buynsters, A. M. A. Pistorius, M. Wang, M. C. Feiters, R. J. M. Nolte, B. Zwanenburg. J. Chem. Soc. Chem. Commun. 1994, 1941-1942;
27. b) ibid. 1994, 2739.
28. N. A. J. M. Sommerdijk, P. J. J. A. Buynsters, H Akdemir, D. G. Geurts, M. C. Feiters, R. J. M. Nolte, B. Zwanenburg, J. Org. Chem. 1997, 62, 4955.
29. This is also supported by the finding that isotherms of 1 recorded at 10, 20 and 30°C all showed a plateau, indicating a liquid expanded (LE)-liquid condensed (LC) coexistence region. The transition pressure was temperature-independent whereas the lift-off area was strongly temperature-dependent. From these results it may be concluded tenlatively that in the LE phase of 1 the molecular area is determined by the conformational motions in the hydrocarbon chains. Apparently, upon further compression this area depends only on the size of the head group. In the compressed state, then, the molecular area will be determined by the head group, which will be less influenced by thermally induced conformational motions due to intermolecular hydrogen bonding. In isotherms of 2 the transition pressure was temperature-dependent and the lift-off area temperature-independent. The molecular area in the LE phase is independent of the conformations of the alkyl chains, but in the LC phase these conformations play a major role in determining the molecular area. Changes in the head group organisation due to conformational motions of the butyrate group would explain the effect of temperature on the molecular area in the LC phase, wheras the overall shape of the molecule accounts for the observed low area per surfactant molecule.
30. a) D. Hönig, D. Möbius, J. Phys. Chem. 1991, 62, 4590-4592;
31. b) S. Hénon, J. Meunier, Rev. Sci. Instrum. 1991, 62, 936-939.
32. Chiral monolayer domains were also observed during fluorescence microscopy experiments using 0.5 mol% sn-1,2-dipalmitoyl-3-glycerolphosphatidylethanolaminesulfurodamine. The size of these domains was drastically reduced compared to the ones observed by Brewster angle microscopy. This remarkable difference is probably due to the fluorescence probe, which acts as an impurity and causes an increase in the number of nucleation sites.
33. The formation of more strongly curved domains at lower temperatures can be attributed to tilting of the surfactant molecules: a) D. J. Keller, H. M. McConnell, V. T. Moy, J. Phys. Chem. 1986, 90, 2310;
34. b) V. T. Moy, D. J. Keller, H. E. Gaub, H. M. McConnell, ibid. 1986, 90, 3198.
35. Z. Reich, L. Zaidman, S. B. Gutman, T. Arad, A. Minski, Biochem. 1994, 33, 14177-14184.
36. a2 values were 11.2 and 10.9.
37. a) R. M. Weis, H. M. McConnell, Nature 1984, 310, 47-49;
38. b) C. M. Knobler, Science, 1990, 249, 870-874.
39. s reflection. See : a) T. Gulik-Krzywicki, E. Rivas, V. Luzzati, J. Mol. Biol. 1967, 27, 303;
40. b) A. Tardieu, V. Luzzati, ibid. 1973, 75, 711;
41. c) J. L. Ranck, L. Mathieu, D. M. Sadler, A. Tardieu, T. Gulik-Krzywicki, V. Luzzati, ibid. 1974, 85, 249.
42. J.-H. Fuhrhop, P. Schnieder, J. Rosenberg, E. Boekema. J. Am. Chem. Soc. 1987, 109, 3387-3390.
43. a values of 3 are assumed to be similar to those of 1 and 2 (see ref. [17]).
44. 4]. See: a) R. J. H. Hafkamp, M. C. Feiters, R. J. M Nolte, Angew. Chem. 1994, 106, 1054; Angew. Chem. Int. Ed. Engl. 1994, 33, 986;
45. 4]. See: a) R. J. H. Hafkamp, M. C. Feiters, R. J. M Nolte, Angew. Chem. 1994, 106, 1054; Angew. Chem. Int. Ed. Engl. 1994, 33, 986;
46. b) J. H. van Esch, M. Damen, M. C. Feiters, R. J. M. Nolte, Reel. Trav. Chim. Pays-Bas 1994, 113, 186-193.
47. -1 is characteristic of a trans-amide polymer structure: N. Colthup, L. Daly, S. Wiberley, Introduction to Infrared and Raman Spectroscopy, Academic Press, New York, 1964, pp. 263-265.
48. -1.
49. -1 (see ref. [23]).
50. -1 occurs in both the spin-dried sample and in the chloroform solution.
51. A. Blume, W. Hubner, G. Messner, Biochem. 1988, 27, 8230.
52. In the models of 2 (Figure 7b) the bridging water molecules between the amide carbonyl and phosphate groups have been omitted for the sake of clarity.
53. 2O, therefore, may offer the possibility of tuning the aggregation behaviour of surfactants by changing the strength of their intermolecular interactions.
54. J. Reedijk, J. Inorg Chem. 1971, 33, 179.
55. -1 is also present, indicating that not all ester groups are involved in hydrogen bonding.
56. No NH-ND exchange was observed for this compound.
57. Compound 4 did not form a stable monolayer.
58. N. A. J. M. Sommerdijk, T. H. L. Hoeks, M. Synak, M. C. Feiters, R. J. M. Nolte, B. Zwanenburg, J. Am. Chem. Soc. 1997, 119, 4338-4344.
59. N. Clark, K. Rothschild, B. Simon, D. Luippold, Biophys. J. 1980, 31, 65.