Self-assembly of rodlike hydrogen-bonded nanostructures [3]

Journal of the American Chemical Society

Volumn 121, Issue 30, 1999, Pages 7154-7155

  Klok, Harm Anton ^a   Jolliffe, Katrina A ^b   Schauer, Caroline L ^c   Prins, Leonard J ^d   Spatz, Joachim P ^d   Möller, Martin ^d   Timmerman, Peter ^d   Reinhoudt, David N ^d  

^a MAX PLANCK INSTITUTE FOR POLYMER RESEARCH   (Germany)

^b UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^c TUFTS UNIVERSITY   (United States)

^d NONE

Author keywords

[No Author keywords available]

Indexed keywords

NANOPARTICLE; POLYMER;

CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; HYDROGEN BOND; LETTER; MOLECULAR WEIGHT; STRUCTURE ANALYSIS;

EID: 0033523247     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9905344     Document Type: Letter

References (23)

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2. For some recent examples, see: (a) Kotera, M.; Lehn, J.-M.; Vigneron, J.-P. J. Chem. Soc., Chem. Commun. 1994, 197-199. (b) Percec, V.; Heck, J.; Lee, M.; Ungar, G.; Alvarez-Castillo, A. J. Mater. Chem. 1992, 2, 1033-1039. (c) Stupp, S. I.; LeBonheur, V.; Walker, K.; Li, L. S.; Huggins, K. E.; Keser, M.; Amstutz, A. Science 1997, 276, 384-389. (d) Sijbesma, R. P.; Beijer, F. H.; Brunsveld, L.; Folmer, B. J. B.; Hirschberg, J. H. K. K.; Lange, R F. M.; Lowe, J. K. L.; Meijer, E. W. Science 1997, 278, 1601-1604. (e) Huck, W. T. S.; van Veggel, F. C. J. M.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1213-1215. (f) Zimmerman, S. C.; Zeng, F.; Reichert, D. E. C.; Kolotuchin, S. V. Science 1996, 71, 1095-1098.
3. For some recent examples, see: (a) Kotera, M.; Lehn, J.-M.; Vigneron, J.-P. J. Chem. Soc., Chem. Commun. 1994, 197-199. (b) Percec, V.; Heck, J.; Lee, M.; Ungar, G.; Alvarez-Castillo, A. J. Mater. Chem. 1992, 2, 1033-1039. (c) Stupp, S. I.; LeBonheur, V.; Walker, K.; Li, L. S.; Huggins, K. E.; Keser, M.; Amstutz, A. Science 1997, 276, 384-389. (d) Sijbesma, R. P.; Beijer, F. H.; Brunsveld, L.; Folmer, B. J. B.; Hirschberg, J. H. K. K.; Lange, R F. M.; Lowe, J. K. L.; Meijer, E. W. Science 1997, 278, 1601-1604. (e) Huck, W. T. S.; van Veggel, F. C. J. M.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1213-1215. (f) Zimmerman, S. C.; Zeng, F.; Reichert, D. E. C.; Kolotuchin, S. V. Science 1996, 71, 1095-1098.
4. For some recent examples, see: (a) Kotera, M.; Lehn, J.-M.; Vigneron, J.-P. J. Chem. Soc., Chem. Commun. 1994, 197-199. (b) Percec, V.; Heck, J.; Lee, M.; Ungar, G.; Alvarez-Castillo, A. J. Mater. Chem. 1992, 2, 1033-1039. (c) Stupp, S. I.; LeBonheur, V.; Walker, K.; Li, L. S.; Huggins, K. E.; Keser, M.; Amstutz, A. Science 1997, 276, 384-389. (d) Sijbesma, R. P.; Beijer, F. H.; Brunsveld, L.; Folmer, B. J. B.; Hirschberg, J. H. K. K.; Lange, R F. M.; Lowe, J. K. L.; Meijer, E. W. Science 1997, 278, 1601-1604. (e) Huck, W. T. S.; van Veggel, F. C. J. M.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1213-1215. (f) Zimmerman, S. C.; Zeng, F.; Reichert, D. E. C.; Kolotuchin, S. V. Science 1996, 71, 1095-1098.
5. For some recent examples, see: (a) Kotera, M.; Lehn, J.-M.; Vigneron, J.-P. J. Chem. Soc., Chem. Commun. 1994, 197-199. (b) Percec, V.; Heck, J.; Lee, M.; Ungar, G.; Alvarez-Castillo, A. J. Mater. Chem. 1992, 2, 1033-1039. (c) Stupp, S. I.; LeBonheur, V.; Walker, K.; Li, L. S.; Huggins, K. E.; Keser, M.; Amstutz, A. Science 1997, 276, 384-389. (d) Sijbesma, R. P.; Beijer, F. H.; Brunsveld, L.; Folmer, B. J. B.; Hirschberg, J. H. K. K.; Lange, R F. M.; Lowe, J. K. L.; Meijer, E. W. Science 1997, 278, 1601-1604. (e) Huck, W. T. S.; van Veggel, F. C. J. M.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1213-1215. (f) Zimmerman, S. C.; Zeng, F.; Reichert, D. E. C.; Kolotuchin, S. V. Science 1996, 71, 1095-1098.
6. For some recent examples, see: (a) Kotera, M.; Lehn, J.-M.; Vigneron, J.-P. J. Chem. Soc., Chem. Commun. 1994, 197-199. (b) Percec, V.; Heck, J.; Lee, M.; Ungar, G.; Alvarez-Castillo, A. J. Mater. Chem. 1992, 2, 1033-1039. (c) Stupp, S. I.; LeBonheur, V.; Walker, K.; Li, L. S.; Huggins, K. E.; Keser, M.; Amstutz, A. Science 1997, 276, 384-389. (d) Sijbesma, R. P.; Beijer, F. H.; Brunsveld, L.; Folmer, B. J. B.; Hirschberg, J. H. K. K.; Lange, R F. M.; Lowe, J. K. L.; Meijer, E. W. Science 1997, 278, 1601-1604. (e) Huck, W. T. S.; van Veggel, F. C. J. M.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1213-1215. (f) Zimmerman, S. C.; Zeng, F.; Reichert, D. E. C.; Kolotuchin, S. V. Science 1996, 71, 1095-1098.
7. Zhong, Q.; Inniss, D, Elings, V. B. Surf. Sci. 1993, 290, L688-L692.
8. (b) Spatz, J. P.; Sheiko, S.; Möller, M.; Winkler, R. G.; Reineker, P.; Marti, O. Nanotechnology 1995, 6, 40-44.
9. (c) Spatz, J. P.; Sheiko, S.; Winkler, R. G.; Reineker, P.; Marti, O.; Möller, M. Langmuir 1997, 13, 4699-4703.
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12. (b) Timmerman, P.; Vreekamp, R. H.; Hulst, R.; Verboom, W.; Reinhoudt, D. N.; Rissanen, K.; Udachin, K. A.; Ripmeester, J. Chem. Eur. J. 1997, 3, 1823-1832.
13. (c) Jolliffe, K. A.; Crego Calama, M.; Fokkens, R.; Nibbering, N. M. M.; Timmerman, P.; Reinhoudt, D. N. Angew. Chem., Int. Ed. 1998, 37, 1294-1297.
14. For a general overview of this work, see: Whitesides, G. M.; Simanek, E. E.; Mathias, J. P.; Seto, C. T.; Chin, D. N.; Mammen, M.; Gordon, D. M. Acc. Chem. Res. 1995, 28, 37-44 and references therein.
15. After submission of this paper, a very similar paper from the Whitesides group was published: Choi, I. S.; Li, X.; Simanek, E. E.; Akaba, R.; Whitesides, G. M. Chem. Mater, 1999, 11, 684.
16. n was obtained by mixing calix[4]arenes 1b and 2b in a 1:1 molar ratio in THF followed by evaporation of the solvent and dissolution in chloroform.
17. Mathias, J. P.; Simanek, E. E.; Whitesides, G. M. J. Am. Chem. Soc. 1994, 116, 4326-4340.
18. Koenig, J. L. Spectroscopy of Polymers; ACS Publications; American Chemical Society: Washington, DC, 1992; Chapter 6.
19. 6 formed large crystals (∼3 × 3 mm in size) from a variety of solvent systems, but none of these crystals gave diffraction data good enough for structure determinations.
20. 6 only showed a broad endotherm around 200 °C (which is much higher than the melting temperatures of the separate components) probably indicating the disintegration of the hydrogen-bonded assembly.
21. 6, and was performed by manual substitution of the propyl for dodecyl (all-trans configuration) side chains followed by a gasphase minimization (CHARMm 3.3, ABNR, rms < 0.001).
22. n the alkyl chains of component 1 mainly determine the lateral dimensions of the strands.
23. n these units are at least 10 Å apart.