Towards modular design of chiroptically switchable molecules based on formation and cleavage of metal-ligand coordination bonds

Synthesis

Volumn , Issue 1, 2010, Pages 49-56

  Soloshonok, Vadim A ^a   Ueki, Hisanori ^a  

^a UNIVERSITY OF OKLAHOMA   (United States)

Author keywords

Chiral molecular switches; Macromolecular ligands; Nickel; Palladium

Indexed keywords

ABSOLUTE CONFIGURATION; CHIRAL AMINES; CHIRAL LIGAND; DIASTEREOMERIC; DIASTEREOMERIC COMPLEXES; EXTERNAL STIMULUS; LIGAND COORDINATION; MACROMOLECULAR LIGANDS; MODULAR DESIGNS; MOLECULAR SWITCHES; PHENONE; SINGLE PRODUCT; STEREO-SELECTIVE; STEREOGENIC AXIS; SWITCHABLE;

CHIRALITY; DESIGN; ENANTIOMERS; MACROMOLECULES; NICKEL ALLOYS; ORGANIC COMPOUNDS; PALLADIUM; PALLADIUM COMPOUNDS; STEREOCHEMISTRY; STRUCTURAL METALS;

LIGANDS;

LIGAND; MOLECULAR SWITCH; NICKEL; ORGANIC COMPOUND; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; CHIRALITY; COMPLEX FORMATION; DIASTEREOISOMER; DISSOCIATION; MACROMOLECULE; REACTION ANALYSIS; SOLID STATE; STEREOCHEMISTRY; STEREOSPECIFICITY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 75749156656     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1217090     Document Type: Article

References (77)

1. Feringa B L., Wiley-VCH Weinheim 2001, Feringa B L., Koumura N, vanDelden R A., terWiel M K. J., Appl. Phys. A 2002 75 301
2. deSilva A P., Gunaratne H Q., Gunnlaugsson T, Huxley A J. M., McCoy C P., Rademacher J T., Rice T E., Chem. Rev. 1997 97 1515
3. Rambidi N G., Microelectron. Eng. 2003 69 485
4. For recent publications, see:, Kapetanakis E, Douvas A M., Velessiotis D, Makarona E, Argitis P, Glezos N, Normand P, Adv. Mater. 2008 20 4568
5. Rath A K., Dhara K, Banerjee P, Pal A J., Langmuir 2008 24 5937
6. Das B C., Pal A J., Org. Electron. 2008 9 39
7. Facchetti A, Letizia J, Yoon M.-H, Mushrush M, Katz H E., Marks T J., Chem. Mater. 2004 16 4715
8. Schindler F, Lupton J M., Mueller J, Feldmann J, Scherf U, Nat. Mater. 2006 5 141
9. Liu Z, Yasseri A A., Loewe R S., Lysenko A B., Malinovskii V L., Zhao Q, Surthi S, Li Q, Misra V, Lindsey J S., Bocian D F., J. Org. Chem. 2004 69 5568
10. Zelikovich L, Libman J, Shanzer A, Nature 1995 374 790
11. Kalny D, Elhabiri M, Moav T, Vaskevich A, Rubinstein I, Shanzer A, Albrecht-Gary A.-M, Chem. Commun. 2002 1426
12. Plenio H, Aberle C, Chem. Eur. J. 2001 7 4438
13. Janek J, Nat. Mater. 2009 8 88
14. Fukui M, Mori T, Inoue Y, Rathore R, Org. Lett. 2007 9 3977
15. Deng J, Song N, Zhou Q, Su Z, Org. Lett. 2007 9 5393
16. Mori T, Inoue Y, J. Phys. Chem. A 2005 109 2728
17. Shie T.-L, Lin C.-H, Lin S.-L, Yang D.-Y, Eur. J. Org. Chem. 2007 4831
18. Roehr H, Trieflinger C, Rurack K, Daub J, Chem. Eur. J. 2006 12 689
19. Siemeling U, Scheppelmann I, Heinze J, Neumann B, Stammler A, Stammler H.-G, Chem. Eur. J. 2004 10 5661
20. Aubert N, Troiani V, Gross M, Solladie N, Tetrahedron Lett. 2002 43 8405
21. Collin [nl]J.-P, Kern J.-M, Raehm L, Sauvage J.-P, Mol. Switches 2001 249
22. Ambroise A, Wagner R W., Rao P D., Riggs J A., Hascoat P, Diers J R., Seth J, Lammi R K., Bocian D F., Holten D, Lindsey J S., Chem. Mater. 2001 13 1023
23. Bissel R A., Lrdova E, Kaifer A E., Stoddart J F., Nature 1994 369 133
24. (b) Ashton, P. R.; Balzani, V.; Becher, J.; Credi, A.; Fyfe, M. C. T.; Mattersteig, G.; Menzer, S.; Nielsen, M. B.; Raymo, F. M.; Stoddart, J. F.; Venturi, M.; Williams, D. J. J. Am. Chem. Soc. 1999, 121, 3951.
25. (c) Bauer, M.; Mgtle, F. V. Chem. Ber. 1992, 125, 1675.
26. (d) Dichtel, W. R.; Miljanic, O. S.; Zhang, W.; Spruell, J. M.; Patel, K.; Aprahamian, I.; Heath, J. R.; Stoddart, J. F. Acc. Chem. Res. 2008, 41, 1750.
27. (e) Stoddart, J. F.; Colquhoun, H. M. Tetrahedron 2008, 64, 8231.
28. (f) Kay, E. R.; Leigh, D. A. Pure Appl. Chem. 2008, 80, 17.
29. (g) Kim, Y.-H.; Goddard, W. A. III J. Phys. Chem. C 2007, 111, 4831.
30. (h) Saha, S.; Stoddart, J. F. Chem. Soc. Rev. 2007, 36, 77.
31. (i) Flood, A. H.; Wong, E. W.; Stoddart, J. F. Chem. Phys. 2006, 324, 280.
32. (j) Stoddart, J. F. Pure Appl. Chem. 2005, 77, 1089.
33. (k) Flood, A. H.; Peters, A. J.; Vignon, S. A.; Steuerman, D. W.; Tseng, H.-R.; Kang, S.; Heath, J. R.; Stoddart, J. F. Chem. Eur. J. 2004, 10, 6558.
34. (l) Steuerman, D. W.; Tseng, H.-R.; Peters, A. J.; Flood, A. H.; Jeppesen, J. O.; Nielsen, K. A.; Stoddart, J. F.; Health, J. R. Angew. Chem. In. Ed. 2004, 43, 6486.
35. For reviews, see: Special issue on Photochromism: Memories and Switches: Chem. Rev. 2000 100 1685-1890
36. Feringa B L., Acc. Chem. Res. 2001 34 504
37. For recent publications, see:, Feringa B L., Delden R A., Wiel M K. J., Mol. Switches 2001 123
38. Oosterling M L. C. M., Schoevaars A M., Haitjema K J., Feringa B L., Isr. J. Chem. 1997 36 341
39. Feringa B L., Huck P M., Schoevaars A M., Adv. Mater. 1996 8 681
40. Pijper D, Jongejan M G. M., Meetsma A, Feringa B L., J. Am. Chem. Soc. 2008 130 4541
41. Geertsema E M., Hoen R, Meetsma A, Feringa B L., Eur. J. Org. Chem. 2006 16 3596
42. Feringa B L., Delden R A., Wiel M K. J., Pure Appl. Chem. 2003 75 563
43. VanDelden R A., TerWiel M K. J., Feringa B L., Chem. Commun. 2004 200
44. Delden R A., Mecca T, Rosini C, Feringa B L., Chem. Europ. J. 2004 10 61
45. Zheng J, Qiao W, Wan X, Gao J P., Wang Z Y., Chem. Mater. 2008 20 6163
46. Wang Z Y., Todd E K., Meng X S., Gao J P., J. Am. Chem. Soc. 2005 127 11552
47. Shinkai S, Ikeda M, Sugasaki A, Takeuchi M, Acc. Chem. Res. 2001 34 494
48. Jiang X, Lim Y.-K, Zhang B J., Opsitnick E A., Baik M.-H, Lee D, J. Am. Chem. Soc. 2008 130 16812
49. Li Y, Wang T, Liu M, Soft Matter 2007 3 1312
50. Qiu Y, Chen P, Guo P, Li Y, Liu M, Adv. Mater. 2008 20 2908
51. Canary J W., Zahn S, Chiu Y.-H, Santos O, Liu J, Zhu L, Enantiomer 2000 5 397
52. Soloshonok V A., Ueki H, Moore J L., Ellis T K., J. Am. Chem. Soc. 2007 129 3512
53. Kawamoto T, Hammes B S., Haggerty B, Yap G P. A., Rheingold A L., Borovik A S., J. Am. Chem. Soc. 1996 118 285
54. Hamuro Y, Geib S J., Hamilton A D., Angew. Chem., Int. Ed. Engl. 1994 33 446
55. Preston A J., Fraenkel G, Chow A, Gallucci J C., Parquette J R., J. Org. Chem. 2003 68 22
56. Ramalingam V, Domaradzki M E., Jang S, Muthyala R S., Org. Lett. 2008 10 3315
57. Ueki H, Ellis T K., Martin C H., Soloshonok V A., Eur. J. Org. Chem. 2003 1954
58. Ueki H, Ellis T K., Martin C H., Bolene S B., Boettiger T U., Soloshonok V A., J. Org. Chem. 2003 68 7104
59. Soloshonok V A., Cai C, Hruby V J., Angew. Chem. In. Ed. 2000 39 2172
60. Soloshonok V A., Cai C, Yamada T, Ueki H, Ohfune Y, Hruby V J., J. Am. Chem. Soc. 2005 127 15296
61. Soloshonok V A., Ueki H, J. Am. Chem. Soc. 2007 129 2426
62. Soloshonok V A., Cai C, Hruby V J., Tetrahedron Lett. 2000 41 135
63. Yamada T, Okada T, Sakaguchi K, Ohfune Y, Ueki H, Soloshonok V A., Org. Lett. 2006 8 5625
64. Soloshonok V A., Belokon Y N., Kuzmina N A., Maleev V I., Svistunova N Y., Solodenko V A., Kukhar V P., J. Chem. Soc., Perkin Trans. 1 1992 1525
65. Soloshonok V A., Cai C, Hruby V J Tetrahedron: Asymmetry, 1999, 10, 4265
66. Soloshonok V A., Cai C, Hruby V J., Tetrahedron: Asymmetry 1999 10 4265, Soloshonok V A., Avilov D V., Kukhar V P., Meervelt L V., Mischenko N, Tetrahedron Lett. 1997 38 4903
67. Soloshonok V A., Avilov D V., Kukhar V P., Tetrahedron: Asymmetry 1996 7 1547
68. Soloshonok V A., Avilov D V., Kukhar V P., Tararov V I., Saveleva T F., Churkina T D., Ikonnikov N S., Kochetkov K A., Orlova S A., Pysarevsky A P., Struchkov Y T., Raevsky N I., Belokon Y N., Tetrahedron: Asymmetry 1995 6 1741
69. Soloshonok V A., Cai C, Hruby V J., Org. Lett. 2000 2 747
70. Soloshonok V A., Ueki H, Ellis T K., Tetrahedron Lett. 2005 46 941
71. Soloshonok V A., Ueki H, Ellis T K., Yamada T, Ohfune Y, Tetrahedron Lett. 2005 46 1107
72. Soloshonok V A., Ellis T K., Synlett 2006 533
73. Soloshonok V A., Ueki H, Ellis T K., Chim. Oggi/Chem. Today 2008 26 51
74. Yamada T, Sakaguchi K, Shinada T, Ohfune Y, Soloshonok V A., Tetrahedron: Asymmetry 2008 19 2789
75. Soloshonok V A., Ueki H, Ellis T K., Synlett 2009 704
76. Ellis T K., Ueki H, Yamada T, Ohfune Y, Soloshonok V A., J. Org. Chem. 2006 71 8572
77. Moore J L., Taylor S M., Soloshonok V A., ARKIVOC 2005 (vi) 287