Chirality induction of polyaniline derivatives through chiral complexation

Tetrahedron Letters

Volumn 45, Issue 24, 2004, Pages 4733-4736

  Shen, Xiuliang ^a   Moriuchi, Toshiyuki ^a   Hirao, Toshikazu ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Chiral complexation; Chirality induction; Polyaniline; Quinonediimine

Indexed keywords

ANILINE DERIVATIVE; BENZOQUINONE DERIVATIVE; IMINE; N,N BIS(4' DIMETHYLAMINOPHENYL) 1,4 BENZOQUINONEDIIMINE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODEL; CHIRALITY; COMPLEX FORMATION; CONFORMATIONAL TRANSITION; CONJUGATE; CRYSTAL STRUCTURE; ENTHALPY; EQUILIBRIUM CONSTANT; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY ANALYSIS;

EID: 2442688864     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.04.073     Document Type: Article

References (30)

1. Salaneck W.R., Clark D.T., Samuelsen E.J. Science and Application of Conductive Polymers. 1990;Adams Hilger, New York
2. Jestin I., Frére P., Blanchard P., Roncali J. Angew. Chem., Int. Ed. 37:1998;942. and references cited therein
3. See also the Nobel lectures of Heeger A.J., MacDiarmid A.G., Shirakawa H. Angew. Chem., Int. Ed. 40:2001
4. Moutet J.C., Saint-Aman E., Tranvan F., Angibeaud P., Utille J.P. Adv. Mater. 4:1992;511
5. Guo H., Knobler C.M., Kaner R.B. Synth. Met. 101:1999;44
6. Egan V., Bernstein R., Hohmann L., Tran T., Kaner R.B. Chem. Commun. 2001;801
7. Majidi M.R., Kane-Maguire L.A.P., Wallace G.G. Polymer. 36:1995;3597
8. Majidi M.R., Kane-Maguire L.A.P., Wallace G.G. Polymer. 37:1996;359
9. Reece D.A., Kane-Maguire L.A.P., Wallace G.G. Synth. Met. 119:2001;101
10. MaCarthy P.A., Huang J., Yang S.-C., Wang H.-L. Langmuir. 18:2002;259
11. Yang Y., Wan M. J. Mater. Chem. 12:2002;897
12. Li W., Wang H.-L. J. Am. Chem. Soc. 126:2004;2278
13. Hirao T., Higuchi M., Ikeda I., Ohshiro Y. J. Chem. Soc., Chem. Commun. 1993;194
14. Hirao T., Higuchi M., Hatano B., Ikeda I. Tetrahedron Lett. 36:1995;5925
15. Higuchi M., Imoda D., Hirao T. Macromolecules. 29:1996;8277
16. Higuchi M., Ikeda I., Hirao T. J. Org. Chem. 62:1997;1072
17. Hirao T., Yamaguchi S., Fukuhara S. Tetrahedron Lett. 40:1999;3009
18. Moriuchi T., Bandoh S., Miyaishi M., Hirao T. Eur. J. Inorg. Chem. 2001;651
19. Moriuchi T., Miyaishi M., Hirao T. Angew. Chem., Int. Ed. 40:2001;3042
20. Moriuchi T., Kamikawa M., Bandoh S., Hirao T. Chem. Commun. 2002;1476
21. Hirao T. Coord. Chem. Rev. 226:2002;81
22. Moriuchi T., Shen X., Saito K., Bandoh S., Hirao T. Bull. Chem. Soc. Jpn. 76:2003;595
23. Shen X., Moriuchi T., Hirao T. Tetrahedron Lett. 44:2003;7711
24. 4 Pd: C, 54.85; H, 4.44; N, 8.82. Found: C, 54.79; H, 4.11; N, 8.56
25. 1.00) indicates the emeraldine base structure consisting of the amine and imine moieties at ca. 1:1 ratio
26. -3 M of the monomer unit under argon
27. 2) was prepared by using the literature method Wei Y., Yang C., Ding T. Tetrahedron Lett. 37:1996;731
28. 3: C, 57.72; H, 4.72; N, 8.80. Found: ((S, S)-3) C, 57.86; H, 4.67; N, 9.11. ((R, R)-3) C, 57.62; H, 4.75; N, 8.95
29. -1
30. w=0.177. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 223573. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44)1223-336-033; e-mail: linstead@ccdc.cam.ac.uk; deposit@ccdc.cam.ac.uk)