Liquid crystal and crystal structure of octahomotetraoxacalix[4]arenes

Journal of Organic Chemistry

Volumn 71, Issue 12, 2006, Pages 4509-4515

  Kohmoto, Shigeo ^b   Someya, Yasunobu ^b   Masu, Hyuma ^a   Yamaguchi, Kentaro ^b   Kishikawa, Keiki ^a  

^a CHIBA UNIVERSITY   (Japan)

^b TOKUSHIMA BUNRI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CRYSTAL PHASE; HOMOOXACALIXARENES; MOIETIES; OCTAHOMOTETRAOXACALIX[4]ARENES;

CRYSTAL STRUCTURE; DIFFERENTIAL SCANNING CALORIMETRY; LIQUID CRYSTALS; SINGLE CRYSTALS; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION ANALYSIS;

AROMATIC HYDROCARBONS;

ALKYL GROUP; CALIXARENE; CARBOXYLIC ACID DERIVATIVE; ESTER; OCTADECANOL; OCTADECYLOXY DERIVATIVE; OCTAHOMOTETRAOXACALIX[4]ARENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONFORMATION; CRYSTAL STRUCTURE; DIFFERENTIAL SCANNING CALORIMETRY; LIQUID CRYSTAL; POLARIZATION MICROSCOPY; SELF ASSEMBLY; SYNTHESIS; X RAY DIFFRACTION;

CALIXARENES; CALORIMETRY, DIFFERENTIAL SCANNING; CARBOXYLIC ACIDS; CRYSTALLIZATION; LIQUID CRYSTALS; MICROSCOPY, POLARIZATION; MOLECULAR STRUCTURE; PHENOLS; X-RAY DIFFRACTION;

EID: 33744910578     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060355m     Document Type: Article

References (56)

1. (a) Gutsche, C. D. Calixarenes Revisited; The Royal Society of Chemistry: Cambridge, England, 1998.
2. (b) Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713-745.
3. (c) Ikeda, A.; Shinkai, S. Chem. Rev. 1997, 97, 1713-1734.
4. (d) Conn, M. M.; Rebek, J., Jr. Chem. Rev. 1997, 97, 1647-1668.
5. (e) Ibach, S.; Prautzsch, V.; Vögtle, F. Acc. Chem. Res. 1999, 32, 729-740.
6. (f) Calixarenes 2001; Asfari, Z., Böhmer, V., Harrowfied, J., Vicens, J., Eds.; Kluwer Academic Publishers: Dordrecht. 2001.
7. (g) Hof, F.; Craig, S. E.; Nuckolls, C.; Rebek, J., Jr. Angew. Chem., Int. Ed. 2002, 41, 1488-1508.
8. Ikeda, A.; Udzu, H.; Yoshimura, M.; Shinkai, S. Tetrahedron 2000, 56, 1825-1832.
9. (a) Vysotsky, M. O.; Thondorf, I.; Böhmer, V. Chem. Commun. 2001, 1890-1891.
10. (b) Shivanyuk, A.; Friese, J. C.; Döring, S.; Rebek, J., Jr. J. Org. Chem. 2003, 68, 6489-6496.
11. (a) Corbellini, F.; Fiammengo, R.; Timmerman, P.; Crego-Calama, M.; Versluis, K.; Heck, A. J. R.; Luyten, I.; Reinhoudt, D. N. J. Am. Chem. Soc. 2002, 124, 6569-6575.
12. (b) Corbellini, F.; Costanzo, L. D.; Crego-Calama, M.; Geremia, S.; Reinhoudt, D. N. J. Am. Chem. Soc. 2003, 125, 9946-9947.
13. Castellano, R. K.; Nuckolls, C.; Eichhorn, S. H.; Wood, M. R.; Lovinger, A. J.; Rebek, J., Jr. Angew. Chem., Int. Ed. 1999, 38, 2603-2606.
14. Lee, M.; Lee, S.; Jiang, L. J. Am. Chem. Soc. 2004, 126, 12724-12725.
15. (a) Yan, X.; Janout, V.; Hsu, J. T.; Regen, S. L. J. Am. Chem. Soc. 2003, 125, 8094-8095.
16. (b) Uragami, T.; Meotoiwa, T.; Miyata, T. Macromolecules 2003, 36, 2041-2048.
17. (c) Ikeda, A.; Hatano, T.; Shinkai, S.; Akiyama, T.; Yamada, S. J. Am. Chem. Soc. 2001, 123, 4855-4856.
18. (a) Xu, B.; Swager, T. M. J. Am. Chem. Soc. 1993, 115, 1159-1160.
19. (b) Komori, T.; Shinkai, S. Chem. Lett. 1993, 1455-1458.
20. (c) Komori, T.; Shinkai, S. Chem. Lett. 1992, 901-904.
21. (d) Lippmann, T.; Dalcanale, E. Gazz. Chim. Ital. 1995, 125, 595-599.
22. Koh, K. N.; Araki, K.; Komori, T.; Shinkai, S. Tetrahedron Lett. 1995, 36, 5191-5194.
23. Xu, B.; Swager, T. M. J. Am. Chem. Soc. 1995, 117, 5011-5012.
24. Yonetake, K.; Nakayama, T.; Ueda, M. J. Mater. Chem. 2001, 11, 761-767.
25. Oh, S.-K.; Nakagawa, M.; Ichimura, K. J. Mater. Chem. 2001, 11, 1563-1569.
26. (a) Gutsche, C. D.; Dhawan, B.; No, K. H.; Muthukrishnan, R. J. Am. Chem. Soc. 1981, 103, 3782-3792.
27. (b) Dhawan, B.; Gutsche, C. D. J. Org. Chem. 1983, 48, 1536-1539.
28. (a) Zerr, P.; Mussrabi, M.; Vicens, J. Tetrahedron Lett. 1991, 32, 1879-1880.
29. (b) Masci, B.; Saccheo, S. Tetrahedron 1993, 49, 10739-10748.
30. (c) Hampton, P. D.; Bencze, Z.; Tong, W.; Daitch, C. E. J. Org. Chem. 1994, 59, 4838-4843.
31. (d) Komatsu, N. Tetrahedron Lett. 2001, 42, 1733-1736.
32. Zinke, A.; Ott, R.; Leggeewie, E.; Hassanein, A.; Zankl, G. Monatsh. Chem. 1956, 87, 552:
33. Chem. Abstr. 1957, 51, 2845c.
34. (a) Zhong, Z.; Ikeda, A.; Shinkai, S. J. Am. Chem. Soc. 1999, 121, 11906-11907.
35. (b) Tsue, H.; Enyo, K.; Hirao, K. Helv. Chim. Acta 2001, 84, 849-859.
36. (c) Miah, M.; Pavey, K. D.; Gun'ko, V. M.; Sheehan, R.; Cragg, P. J. Suprumol. Chem. 2004, 16, 185-192.
37. Masci, B. J. Org. Chem. 2001, 66, 1497-1499.
38. No, K.; Lee, J. H.; Yang, S. H.; Noh, K. H.; Lee, S. W.; Kim, J. S. Tetrahedron 2003, 59, 2403-2407.
39. (a) Masci, B.; Saccheo, S.; Fonsi, M.; Varrone, M.; Finelli, M.; Nierlich, M.; Thuéry, P. Acta Crystallogr. C, 2001, 57, 978-981.
40. (b) Thuéry, P., Nierlich, M.; Vicens J.; Masci, B. J. Chem Soc., Dalton Trans. 2001, 867-874.
41. (c) Komatsu, N.; Chishiro, T. J. Chem. Soc., Perkin Trans. 1 2001, 1532-1537.
42. (d) Masci, B.; Colapietro, M. Portalone, G.; Saccheo, S. Acta Crystallogr. C 2002, 58, 345-346.
43. Nishio, M.; Hirota, M.; Umezawa, Y. The CH/π Interaction; Wiley-VCH: New York, 1998.
44. (a) Baures, P. W.; Rush, J. R.; Schroeder, S. D.; Beatty, A. M. Cryst. Growth Des. 2002, 2, 107-110.
45. (b) Desiraju, G. R. Acc. Chem. Res. 1996, 29, 441-449.
46. Masci, B. Homooxa- and Homoaza-calixarenes. In Calixarenes 2001; Asfari, Z., Böhmen V., Harrowfied, J., Vicens, J., Eds.; Kluwer Academic Publishers: Dordrecht, 2001; Chapter 12.
47. Jaime, C.; Mendoza, J.; Prados, P.; Nieto, P. M.; Sánchez, C. J. Org. Chem. 1991, 56, 3372-3376.
48. Masci, B.; Finelli, M.; Varrone, M. Chem. Eur. J. 1998, 4, 2018-2030.
49. (a) Joachimi, D.; Tschierske, C.; Müller, H.; Wendorff, J. H.; Schneider, L.; Kleppinger, R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1165-1167.
50. (b) Hildebrandt, F.; Schröter, J. A.; Tscierske, C.; Festag, R.; Kleppinger, R.; Wendorff, J. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1631-1633.
51. (c) Kato, T.; Kubota, Y.; Nakano, M.; Uryu, T. Chem. Lett. 1995, 1127-1128.
52. (d) Yamaoka, K.; Kaneko, T.; Gong, J. P.; Osada, Y. Macromolecules 2001, 34, 1470-1476.
53. (e) Kato, T.; Mizoshita, N.; Kishimoto, K. Angew. Chem., Int. Ed. 2006, 45, 38-68.
54. Thomas, R. C.; Houston, J. E.; Crooks, R. M.; Kim, T.; Michalske, T. A. J. Am. Chem. Soc. 1995, 117, 3830-3834.
55. Martín-Rapún, R.; Marcos, M.; Omenat, A.; Barberá, J.; Romero, P.; Serrano, J. L. J. Am. Chem. Soc. 2005, 127, 7397-7403.
56. Sheldrick, G. M. Programs for crystal structure solution (SHELXS-97) and refinement (SHELXL-97); University of Göttingen: Göttingen, Germany, 1997.