Synthesis and association behavior of [4.4.4.4.4.4]metacyclophanedodecayne derivatives with interior binding groups

Angewandte Chemie - International Edition

Volumn 37, Issue 9, 1998, Pages 1285-1287

  Tobe, Yoshito ^a   Utsumi, Naoto ^a   Nagano, Atsushi ^a   Naemura, Koichiro ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Carbocations; Cyclophanes; Host guest chemistry; Macrocycles; Molecular recognition

Indexed keywords

EID: 0032543064     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980518)37:9<1285::AID-ANIE1285>3.0.CO;2-B     Document Type: Article

References (16)

1. Self-association in solution: a) J. Zhang, J. S. Moore, J. Am. Chem. Soc. 1992, 114, 9701; b) A. S. Shetty, J. Zhang, J. S. Moore, ibid. 1996, 118, 1019; discotic nematic liquid crystalline phase: c) J. Zhang, J. S. Moore, ibid. 1994, 116, 2655; highly ordered crystalline structure: d) D. Venkataraman, S. Lee, J. Zhang, J. S. Moore, Nature 1994, 371, 591.
2. Self-association in solution: a) J. Zhang, J. S. Moore, J. Am. Chem. Soc. 1992, 114, 9701; b) A. S. Shetty, J. Zhang, J. S. Moore, ibid. 1996, 118, 1019; discotic nematic liquid crystalline phase: c) J. Zhang, J. S. Moore, ibid. 1994, 116, 2655; highly ordered crystalline structure: d) D. Venkataraman, S. Lee, J. Zhang, J. S. Moore, Nature 1994, 371, 591.
3. Self-association in solution: a) J. Zhang, J. S. Moore, J. Am. Chem. Soc. 1992, 114, 9701; b) A. S. Shetty, J. Zhang, J. S. Moore, ibid. 1996, 118, 1019; discotic nematic liquid crystalline phase: c) J. Zhang, J. S. Moore, ibid. 1994, 116, 2655; highly ordered crystalline structure: d) D. Venkataraman, S. Lee, J. Zhang, J. S. Moore, Nature 1994, 371, 591.
4. Self-association in solution: a) J. Zhang, J. S. Moore, J. Am. Chem. Soc. 1992, 114, 9701; b) A. S. Shetty, J. Zhang, J. S. Moore, ibid. 1996, 118, 1019; discotic nematic liquid crystalline phase: c) J. Zhang, J. S. Moore, ibid. 1994, 116, 2655; highly ordered crystalline structure: d) D. Venkataraman, S. Lee, J. Zhang, J. S. Moore, Nature 1994, 371, 591.
5. a) S. Höger, V. Enkelmann, Angew. Chem. 1995, 107, 2917; Angew. Chem. Int. Ed. Engl. 1995, 34, 2713;
6. a) S. Höger, V. Enkelmann, Angew. Chem. 1995, 107, 2917; Angew. Chem. Int. Ed. Engl. 1995, 34, 2713;
7. b) D. L. Morrison, S. Höger, Chem. Commun. 1996, 2313.
8. Y. Tobe, N. Utsumi, K. Kawabata, K. Naemura, Tetrahedron Lett. 1996, 37, 9325.
9. K. Peak, C. B. Knobler, E. F. Maverick, D. J. Cram, J. Am. Chem. Soc. 1989, 111, 8662.
10. a) C. A. Hunter, J. K. M. Sanders, J. Am. Chem. Soc. 1990, 112, 5525;
11. b) F. Cozzi, M. Cinquini, R. Annuziata, T. Dwyer, J. S. Siegel, J. Am. Chem. Soc. 1992, 114, 5729.
12. -1. Because the model compound 4 adopts a planar conformation, the dipole - dipole repulsion between the neighboring cyano groups must be responsible for the preference of nonplanar geometry of 3.
13. The neutral molecules examined include benzene, halobenzene derivatives, phenol, and aniline.
14. -1). though the former cation has the wrong symmetry and the latter cation is too small to fit the cavity of 3.
15. Because of the instability of the complexes, we w ere not able to obtain crystals suitable for X-ray structure determination. We do not have, therefore, any structural information on the 2:1 complexes.
16. +.