Transfer of π-Conjugated Columnar Stacks from Solution to Surfaces

Journal of the American Chemical Society

Volumn 125, Issue 51, 2003, Pages 15941-15949

  Jonkheijm, Pascal ^a   Hoeben, Freek J M ^a   Kleppinger, Ralf ^a   Van Herrikhuyzen, Jeroen ^a   Schenning, Albertus P H J ^a   Meijer, E W ^a  

^a EINDHOVEN UNIVERSITY OF TECHNOLOGY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

PHOTOPHYSICAL MEASUREMENTS;

ATOMIC FORCE MICROSCOPY; DIMERS; HYDROGEN BONDS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; SURFACE CHEMISTRY; SYNTHESIS (CHEMICAL); TEMPERATURE MEASUREMENT;

AROMATIC POLYMERS;

GLASS; GOLD; GRAPHITE; MICA; OLIGO(4 PHENYLENEVINYLENE); OLIGOMER; SILICONE DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CONCENTRATION RESPONSE; HYDROGEN BOND; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SURFACE PROPERTY; SYNTHESIS; TEMPERATURE DEPENDENCE;

EID: 0345733898     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0383118     Document Type: Article

References (47)

1. Klug, A. Angew. Chem. 1983, 95, 579-596.
2. For reviews, see: (a) Brunsveld, L.; Folmer, B. J. B.; Meijer, E. W.; Sijbesma, R. P. Chem. Rev. 2001, 101, 4071-4097.
3. (b) Prins, L. J.; Reinhoudt, D. N.; Timmerman, P. Angew. Chem., Int. Ed. 2001, 40, 2382-2426.
4. (c) Sherrington, D. C.; Taskinen, K. A. Chem. Soc. Rev. 2001, 30, 83.
5. (d) Bong, D. T.; Clark, T. D.; Granja, J. R.; Ghadiri, M. R. Angew. Chem., Int. Ed. 2001, 40, 988-1011.
6. (e) Ciferri, A. Macromol. Rapid Commun. 2002, 23, 511-529.
7. (f) Hartgerink, J. D.; Zubarev, E. R.; Stupp, S. I. Curr. Opin. Solid State Mater. Sci. 2001, 5, 355-361.
8. For examples, see: (a) Pralle, M. U.; Whitaker, C. M.; Braun, P. V.; Stupp, S. I. Macromolecules 2000, 33, 3550-3556.
9. (b) Klok, H.-A.; Jolliffe, K. A.; Schauer, C. L.; Prins. L. J.; Spatz, J. P.; Möller, M.; Timmerman, P.; Reinhoudt, D. N. J. Am. Chem. Soc. 1999, 121, 7154-7155.
10. (c) Zerowski, J. A.; Seto, C. T.; Wierda, D. A.; Whitesides, G. M. J. Am. Chem. Soc. 1990, 112, 9025-9026.
11. (d) Gottarelli, G.; Mezzina, E.; Spada, G. P.; Carsughi, F.; di Nicola G.; Mariani, P.; Sabaticci, A.; Bonazzi, S. Helv. Chim. Acta 1996, 79, 220-234.
12. (e) Mio, M. J.; Prince. R. B.; Moore, J. S.; Kuebel, C.; Martin, D. C. J. Am. Chem. Soc. 2000, 122, 6134-6135.
13. (f) Percec, V.; Ahn, C.-H.; Ungar, G.; Yeardley, D. J. P.; Möller, M.; Sheiko, S. S. Nature 1998, 391, 161-164.
14. (g) Hirschberg, J. H. K. K.; Brunsveld, L.; Ramzi, A.; Vekemans, J. A. J. M.; Sijbesma, R. P.; Meijer, E. W. Nature 2000, 407, 167-170.
15. For examples, see: (a) Rapaport, H.; Kim, H. S.; Kjaer, K.; Howes, P. B. ; Cohen, S.; Als-Nielsen, J.; Ghadiri, M. R.; Leiserowitz, L.; Lahav. M. J. Am. Chem. Soc. 1999, 121, 1186-1191.
16. (b) van Gorp, J. J.; Vekemans, J. A. J. M.; Meijer, E. W. J. Am. Chem. Soc. 2002, 124, 14759-14769.
17. (c) Fenniri, H.; Deng, B.-L.; Ribbe, A. E. J. Am. Chem. Soc. 2002, 124, 11064-11072.
18. (d) Zubarev, E. R.; Pralle, M. U.; Sone, E. D.; Stupp, S. I. J. Am. Chem. Soc. 2001, 123, 4105-4106.
19. (e) Schönherr, H.; Paraschiv, V.; Zapotoczny, S.; Crego-Calama, M.; Timmerman, P.; Frank, C. W.; Vancso, G. J.: Reinhoudt, D. N. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 5025-5027.
20. (f) Kawasaki, T.; Tokuhiro, M.; Kimizuka, N.; Kunitake, T. J. Am. Chem. Soc. 2001, 123, 6792-6800.
21. (a) Van der Craats, A. M.; Warman, J. M.; Fechtenkötter, A.; Brand, J. D.; Harbison, M. A.; Müllen, K. Adv. Mater. 1999, 11, 1469-1472.
22. (b) Schmidt-Mende, L.; Fechtenkötter, A.; Müllen, K.; Moons, E.; Friend, R. H.; MacKenzie, J. D. Science 2001, 293, 1119-1122.
23. Percec, V.; Glodde, M.; Bera, T. K.; Mlura, Y.; Shlyanovskaya, I.; Singer, K. D.; Balagumsamy, V. S. K.; Helney, P. A.; Schnell, I.; Rapp, A.; Spiess, H.-W.; Hudson, S. D.; Duan, H. Nature 2002, 417, 384-387.
24. (a) Sone, E. D.; Zubarev, E. R.; Stupp, S. I. Angew. Chem., Int. Ed. 2002, 41, 1705-1709.
25. (b) Duan, X.; Huang, Y.; Cui, Y.; Wang, J.; Lieber, C. M. Nature 2001, 409, 66-69.
26. (c) Huang, Y.; Duan, X.; Cui, Y.; Lauhon, L. J.; Kim, K.-H.; Lieber, C. M. Science 2001, 294, 1313-1317.
27. (a) Bachtold, A.; Hadley, P.; Nakanishi, T.; Dekker, C. Science 2001, 294, 1317-1320.
28. (b) Postma, H. W. Ch.; Teepen, T.; Yao, Z.; Grifoni, M.: Dekker, C. Science 2001, 293, 76-79.
29. (a) Tseng, G. Y.; Ellenbogen, J. C. Science 2001, 294, 1293-1294.
30. (b) Chen, J.; Reed, M. A.; Rawlett, A. M.; Tour, J. M. Science 1999. 286, 1550-1552.
31. (c) Gorman, C. B.; Carroll, R. L. Angew. Chem., Int. Ed. 2002, 41, 4378-4400.
32. (a) Schenning, A. P. H. J.; van Hemkhuyzen, J.; Jonkheijm, P.; Chen, Z.; Würthner, F.; Meijer, E. W. J. Am. Chem. Soc. 2002, 124, 10252-10253.
33. (b) Schenning, A. P. H. J.; Jonkheijm, P.; Peeters, E.; Meijer, E. W. J. Am. Chem. Soc. 2001, 123, 409-416.
34. (c) Engelkamp, H.; Middelbeek, S.; Nolte. R. J. M. Nature 1999, 284, 785.
35. (d) Schenning, A. P. H. J.; Kilbinger, A. F. M.; Biscarini, F.; Cavellini, M.; Cooper, H. J.; Derrick, P. J.; Feast, W. J.; Lazzaroni, R.; Leclère, Ph.; McDonnell, L. A.; Meijer, E. W.; Meskers, S. C. J. J. Am. Chem. Soc. 2002, 124, 1269-1275.
36. (e) Schoonbeek, F. S.; van Esch, J. H.; Wegewijs, B.; Rep, D. B. A.; de Haas, M. P.; Klapwijk, T. M.; Kellog, R. M.; Feringa, B. L. Angew. Chem., Int. Ed. 1999, 38, 1393-1397.
37. (f) Würthner, F.; Thalacker, C.; Sautter, A. Adv. Mater. 1999, 11, 754-758.
38. (g) Ajayaghosh, A.; George, S. J. J. Am. Chem. Soc. 2001, 123, 5148-5149.
39. (h) Apperloo, J. J.; Janssen, R. A. J.; Malenfant, P. R. L.; Fréchet, J. M. J. Macromolecules, 2000, 33, 7038-7043.
40. Peeters, E.; Marcos, A.; Meskers, S. C. J.; Janssen, R. A. J. J. Chem. Phys. 2000, 112, 9445-9454.
41. Davydov, A. S. Zh. Eksp. Teor. Fiz. 1948, 18, 210-218.
42. Stryer, L. In Biochemistry, 3rd ed.; W. H. Freeman and Company: New York, 1975.
43. For example, see: Marky, L. A.; Breslauer, K. J. Biopolymers 1987, 26, 1601-1620.
44. This behavior is supported by the SANS data that show that the length of the rigid domains increases going from OPV3 to OPV4 (see SANS paragraph).
45. 26-n-dodecane at elevated temperature (388 K. see Supporting Information) revealed similar features as those in d-chloroform at room temperature. Cooling to 323 K gave rise to broadening of the signals of the aromatic protons indicating aggregation. At room temperature, extreme line broadening was observed.
46. Preliminary quantum chemical calculations reveal that the distance between two adjacent hydrogen-bonded dimers is 0.35 nm and the angle of rotation is close to 12° resulting in a pitch length of 6 nm; Beljonne, D. Personal communication.
47. Meijer, E. W.; Schenning, A. P. H. J. Nature 2002, 319, 353-354.