A catenated cyclic octamine: A noncovalently bonded molecular system without attractive interaction between the two units

Chemistry Letters

Volumn , Issue 9, 1997, Pages 881-882

  Takata, Toshikazu ^a   Shoji, Junko ^a   Furusho, Yoshio ^a  

^a Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0031328558     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1997.881     Document Type: Article

References (15)

1. The term "without attractive interaction" used in this paper means "without attractive interaction enough to hinder the circumrotation of the two rings", but not "without any attractive interaction including van der Waals interaction".
2. J.-L. Weidmann, J.-M. Kern, J.-P. Sauvage, Y. Geerts, D. Muscat, and K. Müllen, J. Chem. Soc., Chem. Comm., 1996, 1243 and references cited therein; Y. Geerts, D. Muscat, and K. Müllen, Macromol. Chem. Phys., 196, 3425 (1995); J. A. Preece and J.F. Stoddart, Macromol. Symp., 98, 527 (1995).
3. J.-L. Weidmann, J.-M. Kern, J.-P. Sauvage, Y. Geerts, D. Muscat, and K. Müllen, J. Chem. Soc., Chem. Comm., 1996, 1243 and references cited therein; Y. Geerts, D. Muscat, and K. Müllen, Macromol. Chem. Phys., 196, 3425 (1995); J. A. Preece and J.F. Stoddart, Macromol. Symp., 98, 527 (1995).
4. J.-L. Weidmann, J.-M. Kern, J.-P. Sauvage, Y. Geerts, D. Muscat, and K. Müllen, J. Chem. Soc., Chem. Comm., 1996, 1243 and references cited therein; Y. Geerts, D. Muscat, and K. Müllen, Macromol. Chem. Phys., 196, 3425 (1995); J. A. Preece and J.F. Stoddart, Macromol. Symp., 98, 527 (1995).
5. A review: D.B. Amabilino and J.F. Stoddart, Chem. Rev., 95, 2725 (1995).
6. A.G. Johnston, D.A. Leigh, R.J. Prichard, and M.D. Deegan, Angew. Chem. Int. Ed. Engl., 34, 1209 (1995).
7. A.G. Johnston, D.A. Leigh, R.J. Prichard, L. Nezhat, J.P. Smart, and M.D. Deegan, Angew. Chem. Int. Ed. Engl., 34, 1912 (1995).
8. The oligomeric mixture (5) contained monocyclic octamide and linear polyamide.
9. It had been impossible to obtain pure cyclic tetramine 4, however, recently Leigh et al. have found unique preparation of pure 4 via rotaxane: A.G. Johnston, D.A. Leigh, A. Murphy, J.P. Smart, and M.D. Deegan, J. Am. Chem. Soc., 118, 10662 (1996). In this experiment, we have obtained 4 as a mixture containing 27% of 5.
10. +].
11. +].
12. A variety of Chromatographic purifications on silica gel, alumina, and polystyrene gel was unsuccessful probably due to the strong adsorption of 6 to such stationary phases under any conditions. Only purification could be performed with octahydrochloride of 6 (obtained as white needle in 97% crude yield). Namely, purification by column chromatography on Sephadex LH-20 using chloroform-methanol mixed solvent as eluent resulted in a satisfactory isolation, although completely pure 6 has not been obtained yet.
13. +].
14. 2), 2.08 (brs, 4H, NH).
15. The coalescence temperature at 500 MHz was 283 K.