Formation of supramolecular polymers and discrete dimers of perylene bisimide dyes based on melamine - Cyanurates hydrogen-bonding interactions

Journal of Organic Chemistry

Volumn 73, Issue 9, 2008, Pages 3328-3335

  Seki, Tomohiro ^a   Yagai, Shiki ^a,b   Karatsu, Takashi ^a   Kitamura, Akihide ^a  

^a CHIBA UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AGGLOMERATION; DIMERS; HYDROGEN BONDS; MELAMINE; MOLECULAR INTERACTIONS; ORGANIC POLYMERS; SUPRAMOLECULAR CHEMISTRY;

CYANURATES; HYDROGEN BONDING INTERACTIONS; PERYLENE BISIMIDE DYES;

DYES;

CYANURIC ACID; DYE; ETHYLENE; MELAMINE; ORGANIC SOLVENT; PERYLENE; POLYMER;

ARTICLE; ATOMIC FORCE MICROSCOPY; CHEMICAL INTERACTION; FIBER; HYDROGEN BOND; LIGHT SCATTERING; SYNTHESIS; THERMOSTABILITY; ULTRAVIOLET SPECTROSCOPY;

EID: 43449091902     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800338f     Document Type: Article

References (50)

1. Supramolecular Dye Chemistry; Würthner, F. Ed.; Topics in Current Chemistry 258; Springer-Verlag: Heidelberg, 2005.
2. Hoeben, F. J. M.; Jonkheijm, P.; Meijer, E. W.; Schenning, A. P. H. J. Chem. Rev. 2005, 105, 1491-1546.
3. Schenning, A. P. H. J.; Meijer, E. W. Chem. Commun. 2005, 3245-3258.
4. Ajayaghosh, A.; Praveen, V. K. Acc. Chem. Res. 2007, 40, 644-656.
5. Schenning, A. P. H. J.; Jonkheijm, P.; Hoeben, F. J. M.; Van Herrikhuyzen, J.; Meskers, S. C. J.; Meijer, E. W.; Herz, L. M.; Daniel, C.; Silva, C.; Phillips, R. T.; Friend, R. H.; Beljonne, D.; Miura, A.; De Feyter, S.; Zdanowska, M.; Uji-I, H.; De Schryver, F. C.; Chen, Z.; Würthner, F.; Mas-Torrent, M.; Den Boer, D.; Durkut, M.; Hadley, P. Synth. Met. 2004, 147, 43-48.
6. Langhals, H. Helv. Chim. Acta 2005, 88, 1309-1343.
7. Würthner, F. Chem. Commun. 2004, 1564-1579.
8. Elemans, J. A. A. W.; van Hameren, R.; Nolte, R. J. M.; Rowan, A. E. Adv. Mater. 2006, 18, 1251 1266.
9. Grimsdale, A. C.; Müllen, K. Angew. Chem., Int. Ed. 2005, 44, 5592-5629.
10. Wasielewski, M. R. J. Org. Chem. 2006, 71, 5051-5066.
11. Li, X.-Q.; Stepanenko, V.; Chen, Z.; Prins, P.; Siebbeles Laurens, D. A.; Würthner, F. Chem. Commun. 2006, 3871-3873.
12. Che, Y.; Datar, A.; Balakrishnan, K.; Zang, L. J. Am. Chem. Soc. 2007, 129, 7234-7235.
13. Balakrishnan, K.; Datar, A.; Naddo, T.; Huang, J.; Oitker, R.; Yen, M.; Zhao, J.; Zang, L. J. Am. Chem. Soc. 2006, 128, 7390-7398.
14. Balakrishnan, K.; Datar, A.; Oitker, R.; Chen, H.; Zuo, J.; Zang, L. J. Am. Chem. Soc. 2005, 127, 10496-10497.
15. Yan, P.; Chowdhury, A.; Holman, M. W.; Adams, D. M. J. Phys. Chem. B 2005, 109, 724-730.
16. Würthner, F.; Hanke, B.; Lysetska, M.; Lambright, G.; Harms, G. S. Org. Lett. 2005, 7, 967-970.
17. Sugiyasu, K.; Fujita, N.; Shinkai, S. Angew. Chem., Int. Ed. 2004, 43, 1229-1233.
18. Kaiser, T. E.; Wang, H.; Stepanenko, V.; Würthner, F. Angew. Chem., Int. Ed. 2007, 46, 5541-5544.
19. Zhang, X.; Chen, Z.; Würthner, F. J. Am. Chem. Soc. 2007, 129, 4886-4887.
20. Würthner, F.; You, C.-C.; Saha-Moller Chantu, R. Chem. Soc. Rev 2004, 33, 133-146.
21. Sautter, A.; Kaletas, B. K.; Schmid, D. G.; Dobrawa, R.; Zimine, M.; Jung, G.; Van Stokkum, I. H. M.; De Cola, L.; Williams, R. M.; Würthner, F. J. Am. Chem. Soc. 2005, 127, 6719-6729.
22. Würthner, F.; Sautter, A. Chem. Commun. 2000, 445-446.
23. Würthner, F.; Sautter, A.; Schmid, D.; Weber, P. J. A. Chem. - Eur. J. 2001, 7, 894-902.
24. Yagai, S.; Monma, Y.; Kawauchi, N.; Karatsu, T.; Kitamura, A. Org. Lett. 2007, 9, 1137-1140.
25. Perylene bisimide assemblies based on multiple hydrogen-bonding interactions: (a) Yagai, S. J. Photochem. Photobiol. C: Photochem. Rev. 2006, 7, 164-182.
26. (b) Würthner, F.; Thalacker, C.; Sautter, A. Adv. Mater. 1999, 11, 754-758.
27. (c) Würthner, F.; Thalacker, C.; Sautter, A.; Schartl, W.; Ibach, W.; Hollricher, O. Chem. - Eur. J. 2000, 6, 3871-3886.
28. (d) Liu, Y.; Zhuang, J.; Liu, H.; Li, Y.; Lu, F.; Gan, H.; Jiu, T.; Wang, N.; He, X.; Zhu, D. ChemPhysChem. 2004, 5, 1210-1215.
29. (e) Sinks, L. E.; Rybtchinski, B.; Iimura, M.; Jones, B. A.; Goshe, A. J.; Zuo, X.; Tiede, D. M.; Li, X.; Wasielewski, M. R. Chem. Mater. 2005, 17, 6295-6303.
30. (f) Yagai, S.; Seki, T.; Karatsu, T.; Kitamura, A.; Würthner, F. Angew Chem., Int. Ed., in press.
31. Yagai, S.; Higashi, M.; Karatsu, T.; Kitamura, A. Chem. Mater. 2004, 16, 3582-3585.
32. Yagai, S.; Higashi, M.; Karatsu, T.; Kitamura, A. Chem. Mater. 2005, 17, 4392-4398.
33. Yagai, S.; Karatsu, T.; Kitamura, A. Langmuir 2005, 21, 11048-11052.
34. Yagai, S.; Higashi, M.; Karatsu, T.; Kitamura, A. Chem. Commun. 2006, 1500-1502.
35. Yagai, S.; Kinoshita, T.; Higashi, M.; Kishikawa, K.; Nakanishi, T.; Karatsu, T.; Kitamura, A. J. Am. Chem. Soc. 2007, 129, 13277-13287.
36. Würthner, F.; Thalacker, C.; Diele, S.; Tschierske, C. Chem. - Eur. J. 2001, 7, 2245-2253.
37. Chen, Z.; Stepanenko, V.; Dehm, V.; Prins, P.; Siebbeles, L. D. A.; Seibt, J.; Marquetand, P.; Engel, V.; Würthner, F. Chem. - Eur. J. 2007, 13, 436-449.
38. Thalacker, C.; Würthner, F. Adv. Funct. Mater. 2002, 12, 209-218.
39. Jonkheijm, P.; Miura, A.; Zdanowska, M.; Hoeben, F. J. M.; De Feyter, S.; Schenning, A. P. H. J.; De Schryver, F. C.; Meijer, E. W. Angew. Chem., Int. Ed. 2004, 43, 74-78.
40. A similar hypsochromically-shifted absorption band was observed for octadecylated perylene bisimide: Struijk, C. W.; Sieval, A. B.; Dakhorst, J. E. J.; van Dijk, M.; Kimkes, P.; Koehorst, R. B. M.; Donker, H.; Schaafsma, T. J.; Picken, S. J.; van de Craats, A. M.; Warman, J. M.; Zuilhof, H.; Sudholter, E. J. R. J. Am. Chem. Soc. 2000, 122, 11057-11066.
41. Brunsveld, L.; Folmer, B. J.; Meijer, E. W.; Sijbesma, R. P. Chem. Rev. 2001, 101, 4071-4098.
42. Lehn, J.-M. Polym. Int. 2002, 51, 825-839.
43. Ciferri, A. Macromol. Rapid Commun. 2002, 23, 511-529.
44. Kato, T.; Mizoshita, N.; Kishimoto, K. Angew. Chem., Int. Ed. 2006, 45, 38-68.
45. Nakanishi, K.; Berova, N. In Circular Dichroism: Principles and Applications; Woody, R., Ed.; VCH Publishers: New York, 1994; pp 361-398.
46. Dehm, V.; Chen, Z.; Baumeister, U.; Prins, P.; Siebbeles, L. D. A.; Würthner, F. Org. Lett. 2007, 9, 1085-1088.
47. Langhals, H.; Ismael, R. Eur. J. Org. Chem. 1998, 1915-1917.
48. Syamakumari, A.; Schenning, A. P. H. J.; Meijer, E. W. Chem. - Eur. J. 2002, 8, 3353-3361.
49. Multiple-hydrogen-bond-directed extended aggregation and dimerization of porphyrin derivatives have been controlled by the atropisomerism of meso-substituents: Arai, S.; Niwa, D.; Nishide, H.; Takeoka, S. Org. Lett. 2007, 9, 17-20.
50. Percec, V.; Ahn, C.-H.; Bera, T. K.; Ungar, G.; Yeardley, D. J. P. Chem. - Eur. J. 1999, 5, 1070-1083.