Self-assembly of multinuclear complexes with enantiomerically pure chiral binaphthoxy imine ligands: Effect of the alkyl spacer connecting two binaphthyl units on the metal binding

Chirality

Volumn 18, Issue 9, 2006, Pages 691-697

  Maeda, Takeshi ^a   Furusho, Yoshio ^a,c   Shiro, Motoo ^b   Takata, Toshikazu ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b RIGAKU CORPORATION   (Japan)

^c JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

Binaphthoxy imine; Circular helicate; Copper complex; Self assembly; Stereospecific

Indexed keywords

ALKYL GROUP; COPPER COMPLEX; COPPER DERIVATIVE; DIAMINE DERIVATIVE; IMINE; LIGAND; NAPHTHALENE DERIVATIVE; NAPHTHYL GROUP; PENTANE; PROPANE;

ARTICLE; CHELATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CIRCULAR DICHROISM; COMPLEX FORMATION; CRYSTAL STRUCTURE; ENANTIOMER; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; METAL BINDING; PRIORITY JOURNAL; STEREOSPECIFICITY; STRUCTURE ANALYSIS; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

EID: 33748801480     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20308     Document Type: Article

References (31)

1. Presented in part: Maeda T. Takata T. Abstracts of papers, Symposium on Molecular Chirality 2005, Osaka, 2005; pp. 46-47.
2. (a) Baxter PNW. Metal ion directed assembly of complex molecular architectures and nanostructures. In: Atwood JL Davies JDE. MacNicol DD. Vögtle V. Sauvage JP. Hosseini MW, editors. Comprehensive supramolecular chemistry Vol. 9. Oxford: Pergamon; 1996; p 165-211.
3. (b) Constable EC. Polynuclear Transition Metal Helicates. In: Atwood JL. Davies JDE. MacNicol DD. Vögtle V. Sauvage JP. Hosseini MW, editors. Comprehensive supramolecular chemistry Vol. 9. Oxford: Pergamon; 1996; p 213-252.
4. (c) Fiedler D. Bergman RG. Raymond KN. Supramolecular catalysis of a unimolecular transformation: Aza-Cope rearrangement within a self-assembled host. Angew Chem Int Ed 2004;43:6748-6751.
5. Yoshizawa M. Takeyama Y. Okano T. Fujita M. Cavity-directed synthesis within a self-assembled coordination cage: highly selective [2 + 2] cross-photodimerization of olefins. J Am Chem Soc 2003;125:3243-3247.
6. (a) Piguet C. Bernardinelli G. Hopfgartner G. Helicates as versatile supramolecular comlexs. Chem Rev 1997;97:2005-2062.
7. (b) Albrecht M. "Let's twist again" double-stranded and circular heicates. Chem Rev 2001;101:3457-3497.
8. (a) Baum G. Constable EC. Fenske D. Housecroft CE. Kulke T. Stereoselective double helicate assembly from chiral 2,2′:6′, 2″:6″,2‴-quaterpyridines, tetrahedral metal centres. Chem Eur J 1999;5:1862-1873.
9. (b) Baum G. Constable EC. Fenske D. Housecroft CE. Kulke T. Neuburger M. Zehnder M. Regio- and diastereo-selective formation of dicopper(I) and disilver(I) double helicates with chiral 6-substituted 2,2′:6′, 2″-terpyridines. J Chem Soc Dalton Trans 1999;2000:945-959.
10. (a) Mürner H. von Zelewsky A Hopfgartner G. Dinuclear metal complex of Cd(II), Zn(II) and Fe(II) with triple-helical structure and predetermined chirality. Inorg Chim Acta 1998;36-39.
11. (b) Mamula O. von Zelewsky A Bark T. Bernardinelli G. Stereoselective synthesis of coordination compounds: self-assembly of a polymeric double helix with controlled chirality Angew Chem Int Ed 1999;38:2945-2948.
12. (c) Muller G. Bünzil JCG. Riehl JP. Suhr D. von Zelewsky A Mürner H. First diastereoselective formation of lanthanide triple helical complexes with a terdentate chiral C2 symmetric ligand. Chem Commun 2002;1522-1523.
13. (a) Annunziata R Benaglia M. Cinquini M. Cozzi F. Woods CR. Siegel JS. Long-distance propagation of stereochemical information by stereoselective synthesis of copper(I) bipyridine helicate. Eur J Org Chem 2001:173-180.
14. (b) Lützen A. Hapke M. G-Raming G. Haase D. Saak W. Synthesis and stereoselective self-assembly of double- and triple-stranded helicates. Angew Chem Int Ed 2002;41:2086-2089.
15. (c) Cantuel M. Bemardinelli G. Muller G. Riehl JP. Piguet C. The first enantiomerically pure helical noncovalent tripod for assembling nine-coordinate lanthanide(III) podates. Inorg Chem 2004;43:1840-1849.
16. (d) Bowyer PK. Porter KA. Rae AD. Willis AC. Wild SB. From helicate to infinite coordination polymer: crystal and molecular structures of silver(I) complexes of readily prepared di-Schiff bases. Chem Commun 1998;1153-1154.
17. (e) Amendola V. Fabbrizzi L. Mangano C. Pallavicini P. Roboli E. Zema M. M and P double helical complexes of copper(I) with bis-imino bis-quinoline enantiomerically pure chiral ligands. Inorg Chem 2000;39:5803-5806.
18. (f) Hamblin J. Childs LJ. Alcock NW. Hannon MJ. Directed one-pot synthesis of enantiopure dinuclear silver(I) and copper(I) metallo- supramilecular double helicates. J Chem Soc Dalton Trans 2002;164-169.
19. (g) Prabaharan R. Fletcher NC. Nieuwenhuyzen M. Self-assembled triple helicates with preferential helicity. J Chem Soc Dalton Trans 2002;602-608.
20. (a) Prevent C. Hewge S. Brand G. Bernardinelli G. Charbonniére LJ. Williams AF. Enantioselective formation of double and triple helicates of silver(I): the rule of stacking interactions Angew Chem Int Ed 1997;36:1287-1289.
21. (a) Mamula O. von Zelewsky A. Bernardinelli G. Completely stereospecific self-assembly of a circular helicate. Angew Chem Int Ed 1998;37:289-293.
22. (b) Bark T. Düggeli M. Stoeckli-Evans H. von Zelewsky A Designed molecules for self-assembly: the controlled formation of two chiral self-assembled polynuclear species with pre-determined configuraion. 2001;40:2848-2851.
23. (c) Mamula O. Monlien FJ. Porquet A. Hopfgartner G. Merbach AE. von Zelewsky A. Self-assembly of multinuclear coordination species with chiral bipyridine ligands: silver complexes of 5,6-CHRAGEN(o,m,p-xylidene) ligands, equilibrium behaviour in solution. Chem Eur J. 2001;7:533-539.
24. (d) Perret-Aebi L-E. von Zelewsky A. Dietrich-Buchecker C. Sauvage J-P. Stereoselective synthesis of a topologically chiral molecule: the trefoil knot Angew Chem Int Ed 2004;43:4482-4485.
25. Kitaura K. Onoyama G. Sakamoto H. Matsuda R. Noro S. Kitagawa S. Immobilization of a metallo Schiff base into a microporous coordination polymer Angew Chem Int Ed 2004;43:2684-2687.
26. Yoshida N. Oshio H. Ito T. Self-assembling tetranuclear copper(II) complex of a bis-bidentate Schiff base: double-helical structure induced by aromatic π-π and CH-π interactions. Chem Commun 1998:63-64.
27. (a) Maeda T. Furusho Y. Takata T. Shiro M. Synthesis of a chiral supramolecular metallacycle by stereospecific self-assembly of Cu (II) ion and diimine ligand. Presented in part at the XXX Int Symp Macrocyclic Chemistry. Dresden; 2005.
28. Hall D. Waters TN. The colour isomerism and structure of some copper co-ordination compounds. Part IV. The structure of N,N′-disalicylidene- ethylenediaminecopper. J Chem Soc 1960:1644-1648.
29. Maeda T. Takeuchi T. Furusho Y. Takata T. Design and synthesis of chiral poly(binaphthyl salen zinc complex) and application of the asymmetric field based on its helical conformation to a catalytic asymmetric reaction. J Polym Sci. Part A 2004;42:4693-4703.
30. Ziegler M. von Zelewsky A. Charge-transfer excited state properties of chiral transition metal coordination compounds studies by chiroptical spectroscopy. Coord Chem Rev 1998;177:257-300.
31. Yoshida N. Oshio H. Ito T. Supramolecular motifs in metal complexes of Schiff bases. J Chem Soc Perkin Trans 2, 2001;1674-1678.