How to distinguish isodesmic from cooperative supramolecular polymerisation

Chemistry - A European Journal

Volumn 16, Issue 1, 2010, Pages 362-367

  Smulders, Maarten M J ^a   Nieuwenhuizen, Marko M L ^a   De Greef, Tom F A ^a   Van Der Schoot, Paul ^a   Schenning, Albertus P H J ^a   Meijer, E W ^a  

^a EINDHOVEN UNIVERSITY OF TECHNOLOGY   (Netherlands)

Author keywords

Polymerization; Reaction mechanisms; Self assembly; Supramolecular chemistry; Uv Vis spectroscopy

Indexed keywords

CHARACTERISATION; CONCENTRATION-DEPENDENT; ISODESMIC; LARGE DATA; POLYMERISATION; POLYMERISATION MECHANISM; POLYMERIZATION REACTION; SELF-ASSEMBLING; SELF-ASSEMBLY SUPRAMOLECULAR CHEMISTRY; TEMPERATURE-DEPENDENT MEASUREMENTS; THERMODYNAMIC PARAMETER; UV/ VIS SPECTROSCOPY;

DISSOLUTION; MACROMOLECULES; POLYMERIZATION; SELF ASSEMBLY; THERMODYNAMICS;

SUPRAMOLECULAR CHEMISTRY;

EID: 73949136056     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200902415     Document Type: Article

References (74)

1. a) J. Ruokolainen, R. Makinen, M. Torkkeli, T. Makela, R. Serimaa, G. Ten Brinke, O. Ikkala, Science 1998, 280, 557-560;
2. b) J. M. J. Fréchet, Proc. Natl. Acad. Sci. USA 2002, 99, 4782-4787;
3. c) T. Kato, N. Mizoshita, K. Kishimoto, Angew. Chem. 2006, 118, 44-74;
4. Angew. Chem. Int. Ed. 2006, 45, 38-68;
5. d) S. Sivakova, S. J. Rowan, Chem. Soc. Rev. 2005, 34, 9-21;
6. e) M. Weck, Polym. Int. 2007, 56, 453-460;
7. f) V. Percec, A. E. Dulcey, V. S. K. Balagurusamy, Y. Miura, J. Smidrkal, M. Peterca, S. Nummelin, U. Edlund, S. D. Hudson, P. A. Heiney, H. Duan, S. N. Magonov, S. A. Vinogradov, Nature 2004, 430, 764-768.
8. a) T. F. A. de Greef, M. M. J. Smulders, M. Wolffs, A. P. H. J. Schenning, R. P. Sijbesma, E. W. Meijer, Chem. Rev. 2009, DOI: 10.1021/cr900181u;
9. b) A. P. H. J. Schenning, E. W. Meijer, Chem. Commun. 2005, 3245-3258;
10. c) Z. Chen, A. Lohr, C. R. Saha-Möller, F. Würthner, Chem. Soc. Rev. 2009, 38, 564-584;
11. d) R. F. Service, Science 2005, 309, 95.
12. R. B. Martin, Chem. Rev. 1996, 96, 3043-3064.
13. P. van der Schoot in Theory of Supramolecular Polymerization, Vol.2 (Ed.: A. Ciferri), Taylor & Francis, London, 2005, pp. 77-106.
14. D. Zhao, J. S. Moore, Org. Biomol. Chem. 2003, 2, 3471-3491.
15. F. Würthner, C. Thalacker, S. Diele, C. Tschierske, Chem. Eur. J. 2001, 7, 2245-2253.
16. a) S. Lahiri, J. L. Thompson, J. S. Moore, J. Am. Chem. Soc. 2000, 122, 11315-11319;
17. b) Y. Tobe, N. Utsumi, K. Kawabata, A. Nagano, K. Adachi, S. Araki, M. Sonoda, K. Hirose, K. Naemura, J. Am. Chem. Soc. 2002, 124, 5350-5364.
18. Z. Chen, V. Stepanenko, V. Dehm, P. Prins, L. D. A. Siebbeles, J. Seibt, P. Marquetand, V. Engel, F. Würthner, Chem. Eur. J. 2007, 13, 436-449.
19. a) V. Simic, L. Bouteiller, M. Jalabert, J. Am. Chem. Soc. 2003, 125, 13148-13154;
20. b) I. A. Nyrkova, A. N. Semenov, A. Aggeli, M. Bell, N. Boden, T. C. B. McLeish, Eur. Phys. J. B 2000, 17, 499-513;
21. c) M. Kastler, W. Pisula, D. Wasserfallen, T. Pakula, K. Müllen, J. Am. Chem. Soc. 2005, 127, 4286-4296;
22. d) M. de Loos, J. van Esch, R. M. Kellogg, B. L. Feringa, Angew. Chem. 2001, 113, 633-636;
23. Angew. Chem. Int. Ed. 2001, 40, 613-616.
24. T. E. Kaiser, V. Stepanenko, F. Würthner, J. Am. Chem. Soc. 2009, 131, 6719-6732.
25. a) M. M. J. Smulders, A. P. H. J. Schenning, E. W. Meijer, J. Am. Chem. Soc. 2008, 130, 606-611;
26. b) Ž. Tomović, J. van Dongen, S. J. George, H. Xu, W. Pisula, P. Leclère, M. M. J. Smulders, S. de Feyter, E. W. Meijer, A. P. H. J. Schenning, J. Am. Chem. Soc. 2007, 129, 16190-16196;
27. c) P. van der Schoot, M. A. J. Michels, L. Brunsveld, R. P. Sijbesma, A. Ramzi, Langmuir 2000, 16, 10076-10083;
28. d) M. Ikeda, T. Nobori, M. Schmutz, J.-M. Lehn, Chem. Eur. J. 2005, 11, 662-668;
29. e) M. Peterca, V. Percec, M. R. Imam, P. Leowanawat, K. Morimitsu, P. A. Heiney, J. Am. Chem. Soc. 2008, 130, 14840-14852.
30. P. Jonkheijm, P. van der Schoot, A. P. H. J. Schenning, E. W. Meijer, Science 2006, 313, 80-83.
31. a) M. Miyauchi, Y. Takashima, H. Yamaguchi, A. Harada, J. Am. Chem. Soc. 2005, 127, 2984-2989;
32. b) Y. Hasegawa, M. Miyauchi, Y. Takashima, H. Yamaguchi, A. Harada, Macromolecules 2005, 38, 3724-3730;
33. c) A. Kraft, F. Osterod, R. Fröhlich, J. Org. Chem. 1999, 64, 6425-6433;
34. d) S. Stončius, E. Orentas, E. Butkus, L. Öhrström, O. F. Wendt, K. Wärnmark, J. Am. Chem. Soc. 2006, 128, 8272-8285.
35. a) L. Allouche, A. Marquis, J.-M. Lehn, Chem. Eur. J. 2006, 12, 7520-7525;
36. b) N. Giuseppone, J.-L. Schmitt, L. Allouche, J.-M. Lehn, Angew. Chem. 2008, 120, 1161-1111;
37. Angew. Chem. Int. Ed. 2008, 47, 2235-2239;
38. c) S. Pappalardo, V. Villari, S. Slovak, Y. Cohen, G. Gattuso, A. Notti, A. Pappalardo, I. Pisagatti, M. F. Parisi, Chem. Eur. J. 2007, 13, 8164-8173.
39. a) A. Arnaud, L. Bouteiller, Langmuir 2004, 20, 6858-6863;
40. b) M. Bellot, L. Bouteiller, Langmuir 2008, 24, 14176-14182;
41. c) V. H. Soto Teilini, A. Jover, J. C. Garcia, L. Galantini, F. Meijide, J. V. Tato, J. Am. Chem. Soc. 2006, 128, 5728-5734;
42. d) P. Delangle, J.-C. Mulatier, B. Tinant, J.-P. Declercq, J.-P. Dutasta, Eur. J. Org. Chem. 2001, 3695-3704.
43. a) W. Wang, J. J. Han, L. Q. Wang, L. S. Li, W. J. Shaw, A. D. Q. Li, Nano Lett. 2003, 3, 455-458;
44. b) T. Seki, S. Yagai, T. Karatsu, A. Kitamura, J. Org. Chem. 2008, 73, 3328-3335;
45. c) H. Fenniri, B.-L. Deng, A. E. Ribbe, K. Hallenga, J. Jacob, P. Thiyagarajan, Proc. Natl. Acad. Sci. USA 2002, 99, 6487-6492;
46. d) J.-H. Ryu, L. Tang, E. Lee, H.-J. Kim, M. Lee, Chem. Eur. J. 2008, 14, 871-881;
47. e) P. G. A. Janssen, P. Jonkheijm, P. Thordarson, J. C. Gielen, P. C. M. Christianen, J. L. J. van Dongen, E. W. Meijer, A. P. H. J. Schenning, J. Mater. Chem. 2007, 17, 2654-2660;
48. f) P. J. Collings, E. J. Gibbs, T. E. Starr, O. Vafek, C. Yee, L. A. Pomerance, R. F. Pasternack, J. Phys. Chem. B 1999, 103, 8474-8481.
49. a) R. Takahashi, Y. Kobuke, J. Am. Chem. Soc. 2003, 125, 2372-2373;
50. b) H. Fenniri, B.-L. Deng, A. E. Ribbe, J. Am. Chem. Soc. 2002, 124, 11064-11072;
51. c) A. R. Hirst, B. Huang, V. Castelletto, I. W. Hamley, D. K. Smith, Chem. Eur. J. 2007, 13, 2180-2188.
52. a) F. Lortie, S. Boileau, L. Bouteiller, C. Chassenieux, B. Deme, G. Ducouret, M. Jalabert, F. Lauprêtre, P. Terech, Langmuir 2002, 18, 1118-1111;
53. b) L. Bouteiller, O. Colombani, F. Lortie, P. Terech, J. Am. Chem. Soc. 2005, 127, 8893-8898;
54. c) E. Obert, M. Bellot, L. Bouteiller, F. Andrioletti, C. Lehen-Ferrenbach, F. Boue, J. Am. Chem. Soc. 2007, 129, 15601-15605;
55. d) E. Kolomiets, E. Buhler, S. J. Candau, J.-M. Lehn, Macromolecules 2006, 39, 1173-1181;
56. e) P. Jonkheijm, F. J. M. Hoeben, R. Kleppinger, J. van Herrikhuyzen, A. P. H. J. Schenning, E. W. Meijer, J. Am. Chem. Soc. 2003, 125, 15941-15949.
57. J. van Gestel, P. van der Schoot, M. A. J. Michels, Langmuir 2003, 19, 1375-1383.
58. a) M. Kasai, S. Asakura, F. Oosawa, Biochim. Biophys. Acta 1962, 57, 22-31;
59. b) F. Oosawa, M. Kasai, J. Mol. Biol. 1962, 4, 10-21.
60. See the Supporting Information.
61. J. van Herrikhuyzen, A. Syamakumari, A. P. H. J. Schenning, E. W. Meijer, J. Am. Chem. Soc. 2004, 126, 10021-10027.
62. a) Y. C. Lin, B. Kachar, R. G. Weiss, J. Am. Chem. Soc. 1989, 111, 5542-5551;
63. b) K. Murata, M. Aoki, T. Suzuki, T. Harada, H. Kawabata, T. Komori, F. Ohseto, K. Ueda, S. Shinkai, J. Am. Chem. Soc. 1994, 116, 6664-6676;
64. c) N. Sreenivasachary, J.-M. Lehn, Proc. Natl. Acad. Sci. USA 2005, 102, 5938-5943;
65. d) S. Yagai, M. Higashi, T. Karatsu, A. Kitamura, Chem. Mater. 2005, 17, 4392-4398.
66. To normalise the data we fitted it with a standard sigmoid equation to arrive at the asymptotic values of the UV/Vis absorption at high and low temperatures. See the Supporting Information for more details.
67. The spread in ΔH and ΔS values is most likely the result of experimental errors.
68. Note that during the self-assembly of 2 the hydrogen-bonded dimer is the actual monomer that self-assembles into helical, one-dimensional stacks.
69. The concentration was expressed as the (dimensionless) volume fraction to be able to use Equation (4).
70. The simplest model that can describe a cooperative self-assembly process requires two equilibrium constants.
71. p is observed. However, to actually measure this effect, rather high concentrations are required (millimolar range) or the use of ultrasensitive DSC is necessary.
72. a becomes close to unity, that is, weakly cooperative self-assembly, it will become difficult to distinguish an isodesmic from a cooperative supramolecular polymerisation mechanism.
73. C. A. Hunter, H. L. Anderson, Angew. Chem. 2009, 121, 7624-7636;
74. Angew. Chem. Int. Ed. 2009, 48, 7488-7499.