Tunable molecular assembly codes direct reaction pathways

Angewandte Chemie - International Edition

Volumn 47, Issue 40, 2008, Pages 7705-7709

  Shaller, Andrew D ^a   Wang, Wei ^a   Gan, Haiyang ^a   Li, Alexander D Q ^a  

^a WASHINGTON STATE UNIVERSITY   (United States)

Author keywords

Molecular recognition; Perylenes; Selectivity; Self assembly; Supramolecular chemistry

Indexed keywords

BOTTLES; CODES (SYMBOLS); MOLECULAR BIOLOGY; MOLECULAR RECOGNITION; MONOMERS;

DIIMIDES; MOLECULAR ASSEMBLIES; PERYLENES; PLANARITY; REACTION PATHWAYS; REACTIVE MONOMERS; SELECTIVITY; SUPRAMOLECULAR CHEMISTRY;

SELF ASSEMBLY;

DRUG DERIVATIVE; IMIDE; PERYLENE; PERYLENETETRACARBOXYLIC DIIMIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY;

IMIDES; MODELS, MOLECULAR; PERYLENE;

EID: 54749097774     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200802606     Document Type: Article

References (34)

1. a) G. M. Whitesides, J. P. Mathias, C. T. Seto, Science 1991, 254, 1312;
2. b) X. Li, D. R. Liu, Angew. Chem. 2004, 116, 4956-4979;
3. Angew. Chem. Int. Ed. 2004, 43, 4848-4870;
4. c) B. Hess, A. Mikhailov, Science 1994, 264, 223-224;
5. d) T. Misteli, J. Cell Biol. 2001, 155, 181-185.
6. a) S. J. Rowan, S. J. Cantrill, G. R. L. Cousins, J. K. M. Sanders, J. F. Stoddart, Angew. Chem. 2002, 114, 938-993;
7. Angew. Chem. Int. Ed. 2002, 41, 898-952;
8. b) P. Mukhopadhyay, P. Zavalij, L. Isaacs, J. Am. Chem. Soc. 2006, 128, 14093-14102.
9. a) G. M. Whitesides, M. Boncheva, Proc. Natl. Acad. Sci. USA 2002, 99, 4769-4774;
10. b) F. J. M. Hoeben, P. Jonkheijm, E. W. Meijer, A. P. H. J. Schenning, Chem. Rev. 2005, 105, 1491-1546.
11. a) M. M. J. Smulders, P. H. J. Schenning, E. W. Meijer, J. Am. Chem. Soc. 2008, 130, 606-611;
12. b) E. A. Meyer, R. K. Castellano, F. Diederich, Angew. Chem. 2003, 115, 1244-1287;
13. Angew. Chem. Int. Ed. 2003, 42, 1210-1250;
14. c) D. H. Busch, Top. Curr. Chem. 2005, 249, 1-65;
15. d) G. J. Gabriel, S. Sorey, B. L. Iverson, J. Am. Chem. Soc. 2005, 127, 2637-2640.
16. a) W. Su, Y. Zhang, C. Zhao, X. Li, J. Jiang, ChemPhysChem 2007, 8, 1857-1862;
17. b) Z. Chen, U. Baumeister, C. Tschierske, F. Wurthner, Chem. Eur. J. 2007, 13, 450-465;
18. c) M. J. Ahrens, L. E. Sinks, B. Rybtchinski, W. Liu, B. A. Jones, J. M. Giaimo, A. V. Gusev, A. J. Goshe, D. M. Tiede, M. R. Wasielewski, J. Am. Chem. Soc. 2004, 126, 8284-8294;
19. d) Y. Li, Y. Li, J. Li, C. Li, X. Liu, M. Yuan, H. Liu, S. Wang, Chem. Eur. J. 2006, 12, 8378-8385.
20. a) X. Zhang, Z. Chen, F. Wurthner, J. Am. Chem. Soc. 2007, 129, 4886-4887;
21. b) H. Langhals, R. Ismael, O. Yuruk, Tetrahedron 2000, 56, 5435-5441;
22. c) C. Kohl, T. Weil, J. Qu, K. Mullen, Chem. Eur. J. 2004, 10, 5297-5310.
23. a) W. Wang, J. J. Han, L.-Q. Wang, L.-S. Li, W. Shaw, A. D. Q. Li, Nano Lett. 2003, 3, 455-458;
24. b) W. Wang, L.-S. Li, G. Helms, H. Zhou, A. D. Q. Li, J. Am. Chem. Soc. 2003, 125, 1120-1121.
25. a) F. Würthner, Chem. Commun. 2004, 1564-1579;
26. b) P. Osswald, F. Wurthner, J. Am. Chem. Soc. 2007, 129, 14319-14326;
27. c) W. Wang, A. D. Bain, L.-Q. Wang, G. J. Exarhos, A. D. Q. Li, J. Phys. Chem. A 2008, 112, 3094-3103.
28. See the Supporting Information for complete experimental details, synthesis, and characterization of compounds 2-3, 5-10, and 18-22, and additional supporting figures and tables.
29. A. D. Q. Li, W. Wang, L. Q. Wang, Chem. Eur. J. 2003, 9, 4594-4601.
30. -1.
31. F. C. Spano, S. C. J. Meskers, E. Hennebicq, D. Beljonne, J. Am. Chem. Soc. 2007, 129, 7044-7054.
32. R. B. Martin, Chem. Rev. 1996, 96, 3043-3064.
33. W. Wang, L. Q. Wang, J. Palmer, G. Exarhos, A. D. Q. Li, J. Am. Chem. Soc. 2006, 128, 11150-11159.
34. W. Wang, A. D. Shaller, A. D. Q. Li, J. Am. Chem. Soc. 2008, 130, 8271-8279.