Detection of the site of an enantioselective interaction between chiral polypinanylsilane and a hydrophobic enantiomer by use of circular dichroism

Chemistry Letters

Volumn , Issue 4, 1997, Pages 361-362

  Shinohara, Ken Ichi ^a   Aoki, Toshiki ^a   Kaneko, Takashi ^a   Oikawa, Eizo ^a  

^a NIIGATA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0031509456     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1997.361     Document Type: Article

References (21)

1. a) T. Aoki, K. Shinohara, and E. Oikawa, Makromol. Chem. Rapid Commun., 13, 565 (1992).
2. b) K. Shinohara, T. Aoki, and E. Oikawa, Polymer, 36, 2403 (1995).
3. c)T. Aoki, A. Maruyama, K. Shinohara, and E. Oikawa, Polym. J., 27, 547 (1995).
4. d) T. Aoki, K. Shinohara, T. Kaneko, and E Oikawa, J. Synth. Org. Chem. Jpn., 54, 525 (1996).
5. e) T. Aoki, K. Shinohara, T. Kaneko, and E. Oikawa, Macromolecules, 29, 4192 (1996).
6. f) T. Aoki, M. Ohshima, K. Shinohara, T. Kaneko, and E. Oikawa, Polymer, 38, 235 (1997).
7. g) Because the CD bands of optically active polymers we synthesized previously were complex and not assignable, the interaction between the polymer and an enantiomer was not clear.
8. a) R. West, L. D David, P. I. Djurovich, K. L. Stearley, K. S. V. Srinivasan, and H. Yu, J. Am. Chem. Soc., 103, 7352 (1981).
9. b) K. Takeda, H. Teramae, and N. Matsumoto, J. Am. Chem. Soc., 108, 8186 (1986).
10. c) S. Gautheir and D. J. Worsfold, Macromolecules, 22, 2213 (1989).
11. M. Fujiki, J. Am. Chem. Soc., 116, 6017 (1994).
12. 2 in pinane), no sell membrane forming ability.
13. 2 in pinane), no self membrane forming ability.
14. The determination of Mw and M̄w/M̄n in GPC analysis was based on polystyrene standards. Eluent, THF, Detector, UV and polarimeter.
15. -4mol/l, solvent, chloroform, cell length; 0.1 mm, temperature, -15 °C.
16. 3
17. -4mol/l, [Enantiomer]/[(+)-poly (MPS)]=100, solvent, chloroform, cell length, 0.1mm, temperature; -15 °C. The UV and CD bands of these enantiomers did not overlap with that of the polymer.
18. The CD change may be caused by the change of the structure of the helix The change of the structure of M-screw may be easier than that of P-screw because M-screw had a looser helix than P-screw.
19. However, we could not experiment on such a membrane separation, because this polymer had no sell membrane forming ability. In addition, we detected no enantioselectivity of this polymer in adsorption because of a low quantity of adsorbed compound.
20. This method can not be applied to compounds which were separated by this membrane, such as tryptophan and mandelic acid, because the polymer and the compound had no common solvents.
21. Since the CD bands of (+)-poly(DPSP) were not assignable, the site of the interaction was not clear in contrast to (+)-poly(MPS).