Photoinitiated Polymerization of Columnar Stacks of Self-Assembled Trialkyl-1,3,5-benzenetricarboxamide Derivatives

Journal of the American Chemical Society

Volumn 125, Issue 51, 2003, Pages 15935-15940

  Masuda, Mitsutoshi ^a,b   Jonkheijm, Pascal ^a   Sijbesma, Rint P ^a   Meijer, E W ^a  

^a EINDHOVEN UNIVERSITY OF TECHNOLOGY   (Netherlands)

^b NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AGGLOMERATION; ATOMIC FORCE MICROSCOPY; COPOLYMERIZATION; FOURIER TRANSFORM INFRARED SPECTROSCOPY; HYDROGEN BONDS; INITIATORS (CHEMICAL); MORPHOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOPOLYMERIZATION; SELF ASSEMBLY; SIZE EXCLUSION CHROMATOGRAPHY; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL); ULTRAVIOLET RADIATION;

PHOTOINITIATORS;

AROMATIC COMPOUNDS;

2,2 DIMETHOXY 2 PHENYLACETOPHENONE; ACETOPHENONE DERIVATIVE; AMIDE; BENZENE DERIVATIVE; CYCLOHEXANE; N (5 SORBYLPENTYL) N',N' DI(N OCTYL)BENZENE 1,3,5 TRICARBOXAMIDE; NANOPARTICLE; POLYMER; SORBIC ACID; TRI 1,3,5 BENZENETRICARBOXAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ATOMIC FORCE MICROSCOPY; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; GEL PERMEATION CHROMATOGRAPHY; HYDROGEN BOND; INFRARED SPECTROSCOPY; MOLECULAR WEIGHT; PHOTOACTIVATION; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SEQUENCE HOMOLOGY; STRUCTURE ANALYSIS; SYNTHESIS; ULTRAVIOLET RADIATION;

EID: 0345733899     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja037927u     Document Type: Article

References (49)

1. Neher, D. Adv. Mater. 1995, 7, 691-701.
2. Disch, S.; Finkelmann, H.; Ringsdorf, H.; Schuhmacher, P. Macromolecules 1995, 28, 2424-2428.
3. Percec, V.; Glodde, M.; Bera, T. K.; Miura, Y.; Shiyanovskaya, I.; Singer, K. D.; Balagumsamy, V. S. K.; Heiney, P. A.; Schnell, I.; Rapp, A.; Spiess, H. W.; Hudson, S. D.; Duan, H. Nature 2002, 419, 384-387.
4. Lightfoot, M. P.; Mair, F. S.; Pritchard, R. G.; Warren, J. E. Chem. Commun. 1999, 1945-1946.
5. (a) Chang, J. Y.; Baik, J. H.; Lee, C. B.; Han, M. J.; Hong, S.-K. J. Am. Chem. Soc. 1997, 119, 3197-3198.
6. (b) Bushey, M. L.; Hwang, A.; Stephens, P. W.: Nuckolls. C. J. Am. Chem. Soc. 2001, 123, 8157-8158.
7. (a) Yasuda, Y.; Iishi, E.; Inada, H.; Shirota, Y. Chem. Lett. 1996, 575-576.
8. (b) Hanabusa, K.; Koto, C.; Kimura, M.; Shirai, H.; Kakehi, A. Chem. Lett. 1997, 429-430.
9. (c) Matsunaga, Y.; Miyajima, N.; Nakayasu, Y.; Sakai, S.; Yonenaga, M. Bull. Chem. Soc. Jpn. 1988, 61, 207-210.
10. (d) Brunsveld, L.; Schenning, A. P. H. J.; Broeren, M. A. C.; Janssen, H. M.; Vekemans, J. A. J. M.; Meijer, E. W. Chem. Lett. 2000, 292-293.
11. (e) Gorp, J. J. v.; Vekemans, J. A. J. M.; Meijer, E. W. J. Am. Chem. Soc. 2002, 124, 14759-14769.
12. Green, M. M.; Reidy, M. P.; Johnson, R. D.; Darling, G.; O'Leary, D. J.; Wilson, G. J. Am. Chem. Soc. 1989, 111, 6452-6454.
13. For reviews, see: (a) Lindsey, J. S. New. J. Chem. 1991, 15, 153-180.
14. (b) Mueller, A.; O'Brien, D. F. Chem. Rev. 2002, 102, 727-758.
15. (c) Tajima, K.; Aida, T. Chem. Commun. 2000, 2412, 2399-2412.
16. (d) Ringsdorf, H.; Schlarb, B.; Venzmer, J. Angew. Chem., Int. Ed. Engl. 1988, 27, 113-158.
17. For examples, see: Gray, D. H.: Hu, S.; Juung, E.; Gin, D. L. Adv. Mater. 1997, 9, 731-735.
18. Broer, D. J.; Lub, J.; Mol, G. N. Nature 1995, 378, 467-468.
19. (a) Percec, V.; Ahn, C.-H.; Ungar, G.: Yeardley, D. J. P.; Möller, M.; Sheiko, S. S. Nature 1998, 391, 161-163.
20. (b) Percec, V.; Ahn, C.-H.; Barboiu, B. J. Am. Chem. Soc. 1997, 119, 12978-12979.
21. (c) Percec, V.; Schlueter, D. Macromolecules 1997, 30, 5783-5790.
22. (d) Percec, V.; Holerca, M. N. Biomacromolecules 2000, 1, 6-16.
23. (e) Percec, V.; Ahn, C. H.; Bera, T. K.; Ungar, G.; Yeardley, D. J. P. Chem.-Eur. J. 1999, 5, 1070-1083.
24. (f) Drager, A. S.; Zangmeister, R. A. P.; Armstrong, N. R.; O'Brien, D. F. J. Am. Chem. Soc. 2001, 123, 3595-3596.
25. (a) Masuda, M.; Hanada, T.; Yase, K.; Shimizu, T. Macromolecules 1998, 31, 9403-9405.
26. (b) Inoue, K.; Ono, Y.; Kanekiyo, Y.; Hanabusa, K.; Shinkai, S. Chem. Lett. 1999, 429-430.
27. (c) Tamaoki, N.; Shimada, S.; Okada, Y.; Belaissaoui, A.; Kruk, G.; Yase, K.; Matsuda, H. Langmuir 2000, 16, 7545-7457.
28. Won, Y. Y.; Davis, H. T.; Bates, F. S. Science 1999, 283, 960-963.
29. Stupp, S. I.; LeBonheur, V.; Walker, K.; Li, L. S.; Huggins, K. E.; Keser, M.; Amstutz, A. Science 1997, 276, 384-389.
30. Natta, G.; Farina, M.; Donati, M. Makromol. Chem. 1961, 43, 251-254.
31. (a) Tieke, B. J. Polym. Sci., Polym. Chem. 1984, 22, 2895-2921.
32. (b) Matsumoto, A.; Nagahama, S.; Odani, T. J. Am. Chem. Soc. 2000, 122, 9109-9119.
33. (c) Tieke, B. Colloid Polym. Sci. 1985, 263, 965-972.
34. (a) Agrawal, R. N.; Rubner, M. F. Macromolecules 1990, 23, 1017-1025.
35. (b) Nallicheri, R. A.; Rubner, M. F. Macromolecules 1991, 24, 526-529.
36. (c) Beckham, H. W.; Rubner, M. F. Macromolecules 1993, 26, 5192-5197.
37. (d) Hammond, P. T.; Rubner, M. F. Macromolecules 1995, 28, 795-805.
38. (a) Sission, T. M.; Srisiri, W.; O'Brien, D. F. J. Am. Chem. Soc. 1998, 120, 2322-2329.
39. (b) Lamparski, H.; O'Brien, D. F. Macromolecules 1995, 28, 1786-1794.
40. Barraud, A.; Rosilio, C.; Ruaudel-Teixier. A. Polym. Prepr. 1978, 19, 179-182.
41. Sirsiri, W.; Sisson, T. M.; O'Brien, D. F.; Mcgrath, K. M.; Han, Y.; Gruner, S. M. J. Am. Chem. Soc. 1997, 119, 4866-4873.
42. Odian, G. Principles of Polymerization. 3rd ed.; A Wiley-Interscience Publication: New York. 1991.
43. Tsuchida, E.; Hasegawa, E.; Kimura, N.; Hatashita, M.; Makino, C. Macromolecules 1992, 25, 207-212.
44. Naf, F.; Degen, P. Helv. Chim. Acta 1971, 54, 1939-1949.
45. See Supporting Information for spectra.
46. Hertler, W. R.; Ovenall, D. W.; Reddy, G. S.; Sogah, D. Y. J. Am. Chem. Soc. 1988, 110, 5841-5853.
47. (a) Kamachi, M.; Umetani, H.; Kuwae, Y.; Nozakura, S. Polym. J. (Tokyo) 1983, 15, 753-761.
48. (b) Matsumoto, A.; Horie, A.; Otsu, T. Makromol. Chem., Rapid Commun. 1991, 12, 681-685.
49. Samori, P.; Francke, V.; Mangel, T.; Müllen, K.; Rabe, J. P. Opt. Mater. 1998, 9, 390-393.