Molecular aggregation behavior of perylene-bridged bis(ß- cyclodextrin) and its electronic interactions upon selective binding with aromatic guests

Journal of Physical Chemistry B

Volumn 114, Issue 1, 2010, Pages 101-106

  Wang, Ke Rang ^a   Guo, Dong Sheng ^a   Jiang, Bang Ping ^a   Sun, Zhan Hu ^a   Liu, Yu ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; BINDING ENERGY; BINDING SITES; BIOCHEMISTRY; COMPLEXATION; CYCLODEXTRINS; DESORPTION; FLUORESCENCE; FOURIER TRANSFORM INFRARED SPECTROSCOPY; INFRARED LASERS; IONIZATION OF LIQUIDS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OPTICAL PROPERTIES; POLYVINYL ALCOHOLS; SILANES; WATER ANALYSIS;

AGGREGATION BEHAVIOR; AGGREGATION CONSTANT; AROMATIC GUESTS; ELECTRONIC INTERACTIONS; ELECTROSTATIC REPULSION; ELEMENTAL ANALYSIS; H NMR SPECTRA; IMINO GROUPS; MALDI-MS; MATRIX-ASSISTED LASER DESORPTION IONIZATION MASS SPECTROMETRY; MOLECULAR AGGREGATION; ORDER OF MAGNITUDE; ORGANIC SOLUTIONS; PERYLENE BISIMIDES; PERYLENES; PHOTOINDUCED ELECTRON-TRANSFER PROCESS; PROTONATED; SELECTIVE BINDING; TEMPERATURE DEPENDENT;

ELECTRON TRANSITIONS;

EID: 75649092237     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp908699b     Document Type: Article

References (44)

1. (a) Ajayaghosh, A.; Praveen, V. K. Acc. Chem. Res. 2007, 40, 644-656.
2. (b) Grimsdale, A. C.; Müllen, K. Angew. Chem., Int. Ed. 2005, 44, 5592-5629.
3. (c) Lee, C. C.; Grenier, C.; Meijer, E. W.; Schenning, A. P. H. J. Chem. Soc. Rev. 2009, 38, 671-683.
4. (d) Ryu, J. H.; Hong, D. J.; Lee, M Chem. Commun. 2008, 1043-1054.
5. (a) Würthner, F. Chem. Commun. 2004, 1564-1579.
6. (b) Elemans, J. A. A. W.; van Hameren, R.; Nolte, R. J. M.; Rowan, A. E. Adv. Mater. 2006, 18, 1251-1266.
7. (c) Wasielewski, M. R. J. Org. Chem. 2006, 71, 5051-5066.
8. Zang, L.; Che, Y.; Moore, J. S. Acc. Chem. Res. 2008, 41, 1596-1608.
9. (a) Lehn, J. M. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4763-4768.
10. (b) Lehn, J. M. Chem. Soc. Rev. 2007, 36, 151-160.
11. (a) Baram, J.; Shirman, E.; Ben-Shitrit, N.; Ustinov, A.; Weissman, H.; Pinkas, I.; Wolf, S. G.; Rybtchinski, B. J. Am. Chem. Soc. 2008, 130, 14966-14967.
12. (b) Gebers, J.; Rolland, D.; Frauenrath, H. Angew. Chem., Int. Ed. 2009, 48, 4480-4483.
13. (a) Hippius, C.; Schlosser, F.; Vysotsky, M. O.; Böhmer, V.; Würthner, F. J. Am. Chem. Soc. 2006, 128, 3870-3871.
14. (b) Hippius, C.; van Stokkum, I. H. M.; Zangrando, E.; Williams, R. M.; Würthner, F. J. Phys. Chem. C 2007, 111, 13988-13996.
15. (c) Hippius, C.; van Stokkum, I. H. M.; Gsänger, M.; Groeneveld, M. M.; Williams, R. M.; Würthner, F. J. Phys. Chem. C 2008, 112, 2476-2486.
16. (d) Hippius, C.; van Stokkum, I. H. M.; Zangrando, E.; Williams, R. M.; Wykes, M.; Beljonne, D.; Würthner, F. J. Phys. Chem. C 2008, 112, 14626-14638.
17. (e) Liu, Y.; Wang, K. R.; Guo, D. S.; Jiang, B. P. Adv. Funct. Mater. 2009, 19, 2230-2235.
18. Liu, Y.; Chen, Y. Acc. Chem. Res. 2006, 39, 681-691.
19. Harada, A. Acc. Chem. Res. 2001, 34, 456-464.
20. (a) Lai, X. H.; Ng, S. C. Tetrahedron Lett. 2004, 45, 4469-4472.
21. (b) Kang, S.; Chen, Y.; Shi, J.; Ma, Y. H.; Liu, Y. Chem. J. Chin. Univ. 2007, 28, 458-461.
22. Langhals, H. Chem. Ber. 1985, 118, 4540-4543.
23. (a) Zhang, X.; Chen, Z.; Würthner, F. J. Am. Chem. Soc. 2007, 129, 4886-4887.
24. (b) Schmidt, C. D.; Böttcher, C.; Hirsch, A. Eur. J. Org. Chem. 2007, 5497-5505.
25. (c) Wang, W.; Wan, W.; Zhou, H. H.; Niu, S.; Li, A. D. Q. J. Am. Chem. Soc. 2003, 125, 5248-5249.
26. (d) Marcon, R. O.; dos Santos, J. G.; Figueiredo, K. M.; Brochsztain, S. Langmuir 2006, 22, 1680-1687.
27. (a) Sadrai, M.; Hadel, L.; Sauers, R. R.; Husain, S.; Krogh-Jespersen, K.; Westbrook, J. D.; Bird, G. R. J. Phys. Chem. 1992, 96, 7988-7996.
28. (b) 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.
29. (a) Seibt, J.; Marquetand, P.; Enge, V.; Chen, Z.; Dehm, V.; Würthner, F. Chem. Phys. 2006, 328, 354-362.
30. (b) Fink, R. F.; Seibt, J.; Engel, V.; Renz, M.; Kaupp, M.; Lochbrunner, S.; Zhao, H. M.; Pfister, J.; Würthner, F.; Engels, B. J. Am. Chem. Soc. 2008, 130, 12858-12859.
31. (a) Shaller, A. D.; Wang, W.; Gan, H.; Li, A. D. Q. Angew. Chem., Int. Ed. 2008, 47, 7705-7709.
32. (b) Wang, W.; Han, J. J.; Wang, L. Q.; Li, L. S.; Shaw, W. J.; Li, A. D. Q. Nano Lett. 2003, 3, 455-458.
33. (c) Wang, W.; Li, L. S.; Helms, G.; Zhou, H. H.; Li, A. D. Q. J. Am. Chem. Soc. 2003, 125, 1120-1121.
34. (d) Li, A. D. Q.; Wang, W.; Wang, L. Q. Chem. - Eur. J. 2003, 9, 4594-4601.
35. (a) Zang, L.; Liu, R.; Holman, M. W.; Nguyen, K. T.; Adams, D. M. J. Am. Chem. Soc. 2002, 124, 10640-10641.
36. (b) Daffy, L. M.; de Silva, A. P.; Gunaratne, H. Q. N.; Huber, C.; Lynch, P. L. M.; Werner, T.; Wolfbeis, O. S. Chem. - Eur. J. 1998, 4, 1810-1815.
37. Chen, Z.; Lohr, A.; Saha-Möller, C. R.; Würthner, F. Chem. Soc. Rev. 2009, 38, 564-584.
38. Würthner, F.; Thalacker, C.; Diele, S.; Tschierske, C. Chem. - Eur. J. 2001, 7, 2245-2253.
39. (a) van der Boom, T.; Hayes, R. T.; Zhao, Y.; Bushard, P. J.; Weiss, E. A.; Wasielewski, M. R. J. Am. Chem. Soc. 2002, 124, 9582-9590.
40. (b) Würthner, F.; Chen, Z.; Hoeben, F. J. M.; Osswald, P.; You, C. C.; Jonkheijm, P. v.; Herrikhuyzen, J.; Schenning, A. P. H. J.; van der Schoot, P. P. A. M.; Meijer, E. W.; Beckers, E. H. A.; Meskers, S. C. J.; Janssen, R. A. J. J. Am. Chem. Soc. 2004, 126, 10611-10618.
41. (c) Mathew, S.; Johnston, M. R. Chem. - Eur. J. 2009, 15, 248-253.
42. (a) Yang, H.; Bohne, C. J. Phys. Chem. 1996, 100, 14533-14539.
43. (b) Hollas, M.; Chung, M. A.; Adams, J. J. Phys. Chem. B 1998, 102, 2947-2953.
44. Inoue, Y.; Yamamoto, K.; Wada, T.; Everitt, S.; Gao, X. M.; Hou, Z. J.; Tong, L. H.; Jiang, S. K.; Wu, H. M. J. Chem. Soc., Perkin Trans. 2 1998, 1807-1816.