4′-Bromo-2′,3′,5′,6′-tetrafluorostilbazole: Donor and acceptor site for halogen bonding and π-stacking in one rigid-rod-type molecule

Crystal Growth and Design

Volumn 5, Issue 5, 2005, Pages 1671-1673

  Lucassen, André C B ^a   Vartanian, Maida ^a   Leitus, Gregory ^a   Van Der Boom, Milko E ^a  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 25444483107     PISSN: 15287483     EISSN: None     Source Type: Journal    
DOI: 10.1021/cg0501433     Document Type: Article

References (50)

1. (a) Braga, D.; Brammer, L.; Champness, N. R. CrystEng-Comm 2005, 7, 1.
2. (b) Aizenberg, J. Adv. Mater. 2004, 16, 1295.
3. (c) Almarsson, O.; Zaworotko, M. J. Chem. Commun. 2004, 17, 1889.
4. Kitagawa, S.; Kitaura, R.; Noro, S. Angew. Chem., Int. Ed. 2004, 43, 2334.
5. (e) Nassimbeni, L. R. Acc. Chem. Res. 2003, 36, 631.
6. (f) Jones, W.; Rao, C. N. R. Some Aspects of Supramolecular Design of Organic Materials: Cambridge University Press: Cambridge, 2002.
7. (g) Evans, O. R.; Lin, W. Acc. Chem. Res. 2002, 35, 511.
8. (a) Prins, L. J.; Reinhoudt, D. N.; Timmerman, P. Angew. Chem., Int. Ed. 2001, 40, 2382.
9. (b) Muller-Dethlefs, K.; Hobza, P. Chem. Rev. 2000, 100, 143.
10. (c) Aacheroey, C. B.; Seddon, K. R. Chem. Soc. Rev. 1993, 22, 397.
11. For recent reviews on host-guest interactions, see (a) Gohlke, H.; Klebe, G. Angew. Chem., Int. Ed. 2002, 41, 2644.
12. (b) Cafeo, G.; Gattuso, G.; Kohnke, F. H.; Notti, A.; Occhipinti, S.; Pappalardo, S.; Parisi, M. F. Angew. Chem., Int. Ed. 2002, 41, 2122.
13. (c) Lavigne, J. J.; Anslyn, E. V. Angew. Chem., Int. Ed. 2001, 40, 3118.
14. (a) Nguyen, H. L.; Horton, P. N.; Hursthouse, M. B.; Legon, A. C.; Bruce, D. W. J. Am. Chem. Soc. 2004, 126, 16.
15. (b) Legon, A. C. Angew. Chem., Int. Ed. 1999, 38, 2686.
16. Caronna, T.; Liantonio, R.; Logothetis, T. A.; Metrangolo, P.; Pilati, T.; Resnati, G. J. Am. Chem. Soc. 2004, 126, 4500.
17. (a) Logothetis, T. A.; Meyer, F.; Metrangolo, P.; Pilati, T.; Resnati, G. New J. Chem. 2004, 28, 760.
18. (b) Fox, D. B.; Liantonio, R.; Metrangolo, P.; Pilati, T.; Resnati, G. J. Fluor. Chem. 2004, 125, 271.
19. (c) Forni, A.; Metrangolo, P.; Pilati, T.; Resnati, G. Cryst. Growth Des. 2004, 4, 291.
20. Crihfield, A.; Hartwell, J.; Phelps, D.; Walsh, R. B.; Harris, J. L.; Payne, J. F.; Pennington, W. T.; Hanks, T. W. Cryst. Growth Des. 2003, 3, 313.
21. Messina, M. T.; Metrangolo, P.; Pappalardo, S.; Parisi, M. F.; Pilati, T.; Resnati, G. Chem. Eur. J. 2000, 6, 3495.
22. Metrangolo, P.; Neukirch, H.; Pilati, T.; Resnati, G. Acc. Chem. Res. 2005, 38, 386;
23. Metrangolo, P.; Resnati, G. Chem. Eur. J. 2001, 7, 2511.
24. Zou, J.-W.; Jiang, Y.-J.; Guo, M.; Hu, G.-X.; Zhang, B.; Liu, H.-C.; Yu, Q.-S. Chem. Eur. J. 2005, 11, 740.
25. Valerio, G.; Raos, G.; Meille, S. V.; Metrangolo, P.; Resnati, G. J. Phys. Chem. A, 2000, 104, 1617.
26. Glaser, R.; Chen, N.; Wu, H.; Knotts, N.; Kaupp, M. J. Am. Chem. Soc. 2004, 126, 4412.
27. Berski, S.; Ciunik, Z.; Drabent, K.; Latajka, Z.; Panek, J. J. Phys. Chem. B 2004, 108, 12327.
28. Bond, A. D.; Griffiths, J.; Rawson, J. M.; Hulliger, J. Chem. Commun. 2001, 2488.
29. (a) Fourmigue, M.; Batail, P. Chem. Rev. 2004, 104, 5379.
30. Zhu, S.; Xing, C.; Xu, W.; Jin, G.; Li, Z. Cryst. Growth Des. 2004, 4, 53.
31. Metrangolo, P.; Pilati, T.; Resnati, G.; Stevenazzi, A. Chem. Commun. 2004, 13, 1492.
32. Auffinger, P.; Hays, F. A.; Westhof, E.; Ho, P. S. Proc. Nat. Acad. Sci., U.S.A. 2004, 101, 16789.
33. 4: C, 47.02; H. 1.82. Found C, 46.94; H, 1.77.
34. -3. Structural data for compound 1 has been deposited in the Cambridge Crystallographic Data Centre under CCDC 274127, and can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html.
35. Hoeben, F. J. M.; Jonkheijm, P.; Meijer, E. W.; Schenning, A. P. H. J. Chem. Rev. 2005, 105, 1491.
36. Lorance, E. D.; Kramer, W. H.; Gould, I. R. J. Am. Chem. Soc. 2002, 124, 15225.
37. Kim, C.-Y.; Chandra, P. P.; Jain, A.; Christianson, D. W. J. Am. Chem. Soc. 2001, 123, 9620.
38. (a) Filip-Granit, N.; Yerushalmi, R.; Brandis, A.; van der Boom, M. E.; Scherz, A. J. Phys. Chem. B 2005, 109, 6933.
39. (b) Shukla, A. D.; Strawser, D.; Lucassen, A. C. B.; Freeman, D.; Cohen, H.; Jose, D. A.; Das, A.; Evmenenko, G.; Dutta, P.; van der Boom, M. E. J. Phys. Chem. B. 2004, 108, 17505.
40. (c) Yerushalmi, R.; Scherz, A.; van der Boom, M. E. J. Am. Chem. Soc. 2004, 126, 2700.
41. (d) van der Boom, M. E. Angew. Chem., Int. Ed. 2002, 41, 3363.
42. (e) Würthner, F.; Wortmann, R.; Meerholz, K. ChemPhysChem 2002, 3, 17.
43. (f) Shi, Y.; Zhang, C.; Zhang, H.; Bechtel, J. H.; Dalton, L. R.; Robinson, B. H.; Steier, W. H. Science 2000, 288, 119.
44. (g) Dela Cruz, J. L.; Blanchard, G. J. J. Phys. Chem. A 2002, 106, 10718.
45. (a) Reichenbächer, K.; Süss, H. I.; Hulliger, J. Chem. Soc. Rev. 2005, 34, 22.
46. (b) Vangala, V. R.; Nangia, A.; Lynch, V. M. Chem. Commun. 2002, 1304.
47. (c) Collings, J. C.; Roscoe, K. P.; Li, R.; Thomas; Batsanov, A. S.; Stimson, L. M.; Howard, J. A. K.; Marder, T. B. New. J. Chem. 2001, 25, 1410.
48. (a) van der Boom, M. E.; Marks, T. J. Polymers for Microelectronics and Nanoelectronics; ACS Symposium Series; American Chemical Society: Washington, DC, 2004; Vol. 874, pp 30-43.
49. (b) Yitzchaik, S.; Marks, T. J. Acc. Chem. Res. 1996, 29, 197.
50. (c) DeQuan, L. Ratner, M. A.; Marks, T. J.; Zhang, C.; Yang, J.; Wong, G. K. J. Am. Chem. Soc. 1990, 112, 7389.