Optically active polyoxotungstates bearing chiral organophosphonate substituents

European Journal of Inorganic Chemistry

Volumn , Issue 34, 2009, Pages 5164-5174

  Carraro, Mauro ^a   Modugno, Gloria ^a   Sartorel, Andrea ^a   Scorrano, Gianfranco ^a   Bonchio, Marcella ^a  

^a UNIVERSITY OF PADOVA   (Italy)

Author keywords

Chirality; Circular dichroism; Organic inorganic hybrid composites; Phosphorus; Polyoxometalates

Indexed keywords

CHARGE TRANSFER; CHIRALITY; CIRCULAR DICHROISM SPECTROSCOPY; ELECTRODEPOSITION; ELECTROSPRAY IONIZATION; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC-INORGANIC MATERIALS; PHOSPHORUS; SULFUR COMPOUNDS; ULTRAVIOLET VISIBLE SPECTROSCOPY;

FUNCTIONALIZED; HYBRID COMPOUNDS; KEGGIN-TYPE; OPTICALLY ACTIVE; ORGANIC-INORGANIC HYBRID COMPOSITES; ORGANICS; ORGANOPHOSPHONATES; PHOSPHORYL GROUPS; POLYOXOMETALATES; POLYOXOTUNGSTATES;

DICHROISM;

EID: 72949089289     PISSN: 14341948     EISSN: 10990682     Source Type: Journal    
DOI: 10.1002/ejic.200900728     Document Type: Article

References (96)

1. a) M. T. Pope, A. Müller (Eds.), Polyoxometalate Chemistry from Topology via Self-Assembly to Applications, Kluwer Academic Publishers, Dordrecht, The Netherlands, 2001;
2. b) J. J. Borras-Almenar, E. Coronado, A. Müller, M. T. Pope (Eds.), Polyoxometalate Molecular Science, Kluwer Academic Publishers, Dordrecht, The Netherlands, 2003;
3. D. L. Long, E. Burkholder, L. Cronin, Chem. Soc. Rev. 2007, 36, 105-121.
4. a) K. Kamata, K. Yonehara, Y. Sumida, K. Yamaguchi, S. Hikichi, N. Mizuno, Science 2003, 300, 964-966;
5. b) A. Sartorel, M. Carraro, A. Bagno, G. Scorrano, M. Bonchio, Angew. Chem. Int. Ed. 2007, 46, 3255-3258.
6. a) M. Bonchio, M. Carraro, G. Scorrano, U. Kortz, Adv. Synth. Catal. 2005, 347, 1909-1912;
7. b) M. Bonchio, M. Carraro, A. Farinazzo, A. Sartorel, G. Scorrano, U. Kortz, J. Mol. Catal. A 2007, 262, 36-40;
8. A. Sartorel, M. Carraro, R. De Zorzi, S. Geremia, N. D. McDaniel, S. Bernhard, G. Scorrano, M. Bonchio, J. Am. Chem. Soc. 2008, 130, 5006-5007.
9. A. Proust, R. Thouvenot, P. Gouzerh, Chem, Commun. 2008, 1837-1852.
10. M. Carraro, L. Sandei, A. Sartorel, G. Scorrano, M. Bonchio, Org. Lett. 2006, 8, 3671-3674.
11. a) D. A. Judd, J. H. Nettles, N. Nevins, J. P. Snyder, D. C. Liotta, J. Tang, J. Ermolieff, R. F. Schinazi, C. L. Hill, J. Am. Chem. Soc. 2001, 23, 886-897;
12. b) S. Shigeta, S. Mori, E. Kodama, J. Kodama, K. Takahashi, T. Yamase, Antiviral Res. 2003, 58, 265-271;
13. X. Wang, J. Liu, M. T. Pope, Dalton Trans. 2003, 957-960;
14. Y. Tajima, Microbiol. Immunol. 2003, 47, 207-212.
15. C. Sanchez, G. J. de Soler-Illia, F. Ribot, T. Lalot, C.R. Mayer, V. Cabuil, Chem. Mater. 2001, 13, 3061-3083.
16. P. Gouzerh, A. Proust, Chem. Rev. 1998, 98, 77-112.
17. Z. Peng, Angew. Chem. Int. Ed. 2004, 43, 930-935.
18. J. R. Longa, O. M. Yaghib, Chem. Soc. Rev. 2009, 38, 1213-1214.
19. Z. Zhang, Y. F. Song, L. Cronin, T. Liu, J. Am. Chem. Soc. 2008, 130, 14408-14409.
20. M. Carraro, A. Sartorel, G. Scorrano, C Maccato, M. H. Dickman, U. Kortz, M. Bonchio, Angew. Chem. Int. Ed. 2008, 47, 7275-7279.
21. C. R. Mayer, R. Thouvenot, Chem. Mater. 2000, 12, 257-260.
22. S. Nlate, L. Plault, D. Astruc, Chem. Eur. J. 2006, 12, 903-914.
23. a) S. Favette, B. Hasenknopf, J. Vaissermann, P. Gouzerh, C. Roux, Chem. Commun. 2003, 2664-2665;
24. b) Z. H. Peng, Angew. Chem. Int. Ed. 2004, 43, 930-935.
25. C. R. Mayer, S. Neveu, V. Cabuil, Angew. Chem. Int. Ed. 2002, 41, 501-503.
26. a) M. Bonchio, M. Carraro, G. Scorrano, E. Fontananova, E. Drioli, Adv. Synth. Catal. 2003, 345, 1119-1126;
27. b) M. Carraro, M. Gardan, G. Scorrano, E. Drioli, E. Fontananova, M. Bonchio, Chem. Commun. 2006, 4533-4535.
28. M. Bonchio, M. Carraro, A. Bagno, G. Scorrano, Adv. Synth, Catal. 2004, 346, 648-654.
29. a) I. Bar-Nahum, R. Neumann, Chem. Commun. 2003, 2690-2691;
30. b) I. Bar-Nahum, H. Cohen, R. Neumann, Inorg. Chem. 2003, 42, 3677-3684.
31. K. Micoine, B. Hasenknopf, S. Thorimbert, E. Lacôte, M. Malacria, Angew. Chem. Int. Ed. 2009, 48, 3466-3468.
32. a) J. Schemberg, K. Schneider, U. Demmer, E. Warkentin, A. Müller, U. Ermler, Angew. Chem. Int. Ed, 2007, 46, 2408-2413;
33. corrigendum: Angew. Chem. Int. Ed. 2007, 46, 2970;
34. b) G. Zhang, B. Keita, C. T. Craescu, S. Miron, P. de Oliveira, L. Nadjo, Biomacromolecules 2008, 9, 812-817.
35. J. Li, S. Hu, S. Luo, J.-P. Cheng, Eur. J. Org. Chem. 2009, 132-140.
36. a) B. Hasenknopf, K. Micoine, E. Lacôte, S. Thorimbert, M. Malacria, R. Thouvenot, Eur. J. Inorg. Chem. 2008, 5001-5013;
37. b) H. T. Evans, J. S. Showell, J. Am. Chem. Soc. 1969, 91, 6881-6882;
38. J. Fuchs, R. Palm, Z. Naturforsch. B: Chem. Sci. 1988, 43, 1529-1537;
39. C. M. Tourné, G. F. Tourné, F. Zonnevijlle, J. Chem. Soc., Dalton Trans. 1991, 143-155;
40. e) K. Nomiya, R. Kobayashi, M. Miwa, T. Hori, Polyhedron 1984, 3, 1071-1076;
41. f) J. F. Garvey, M. T. Pope, Inorg. Chem. 1978, 17, 1115-1118.
42. D. Laurencin, R. Villanneau, A. Proust, A. Brethon, I. W. C. E. Arends, R. A. Sheldon, Tetrahedron: Asymmetry 2007, 18, 367-371.
43. H. Q. Tan, Y. G. Li, Z. M. Zhang, C. Qin, X. L. Wang, E. B. Wang, Z. M. Su, J. Am. Chem. Soc. 2007, 129, 10066-10067.
44. [26]Y. Hou, X. Fang, C. L. Hill, Chem. Eur. J. 2007, 13, 9442-9447.
45. a) M. Inoue, T. Yamase, Bull. Chem. Soc. Jpn. 1996, 69, 2863-2868;
46. b) D. L. Long, P. Kögerler, L. J. Farrugia, L. Croning, Chem. Asian J. 2006, 1, 352-357;
47. X. K. Fang, T. M. Anderson, C. L. Hill, Angew. Chem. Int. Ed. 2005, 44, 3540-3544;
48. X. K. Fang, T. M. Anderson, Y. Hou, C. L. Hill, Chem. Commun. 2005, 5044-5046;
49. e) L. M. Zheng, T. Whitfield, X. Wang, A. J. Jacobson, Angew. Chem. Int. Ed. 2000, 39, 4528-4531;
50. H. Q. Tan, Y. G. Li, Z. M. Zhang, C. Qin, X. L. Wang, E. B. Wang, Z. M. Su, J. Am. Chem. Soc. 2007, 129, 10066-10067.
51. a) F. Hussain, U. Kortz, Chem. Commun. 2005, 1191-1193;
52. b) V. Artero, D. Laurencin, R. Villanneau, R. Thouvenot, P. Herson, P. Gouzerh, A. Proust, Inorg. Chem. 2005, 44, 2826-2835.
53. a) M. Inoue, T. Yamase, Bull. Chem. Soc Jpn. 1995, 68, 30553063;
54. b) U. Kortz, M. G. Savelieff, F. Y. A. Ghali, L. M. Khalil, S. A. Maalouf, D. I. Sinno, Angew. Chem. Int. Ed, 2002, 41, 4070-4073.
55. a) C. Streb, D. L. Long, L. Croning, Chem. Commun. 2007, 471-473;
56. b) H. Y. An, E. B. Wang, D. R. Xiao, Y. G. Li, Z. M. Su, L. Xu, Angew. Chem. Int. Ed. 2006, 45, 904-908.
57. a) Y. Q. Lan, S. L. Li, Z. M. Su, K. Z. Shao, J. F. Ma, X. L. Wang, E. B. Wang, Chem. Commun. 2008, 58-60;
58. b) Y. Q. Lan, S. L. Li, X. L. Wang, K. Z. Shao, D. Y. Du, Z. M. Su, E. B. Wang, Chem. Eur. J. 2008, 14, 9999-10006.
59. a) N. Avarvari, J. D. Wallis, J. Mater. Chem. 2009, 19, 4061-4076;
60. b) E. Coronado, J. R. Galan-Mascaros, J. Mater. Chem. 2005, 15, 66-74;
61. P. Gerbier, N. Domingo, J. Gómez-Segura, D. Ruiz-Molina, D. B. Amabilino, J. Tejada, B. E. Williamson, J. Veciana, J. Mater. Chem. 2004, 14, 2455-2460.
62. S. Bareyt, S. Piligkos, B. Hasenknopf, P. Gouzerh, E. Lacôte, S. Thorimbert, M. Malacria, J. Am. Chem. Soc, 2005, 127, 6788-6794.
63. M. Lu, J. Kang, D. Wang, Z. Peng, Inorg. Chem. 2005, 44, 7711-7713.
64. R. L. Augustine, S. K. Tanielyan, N. Mahata, Y. Gao, A. Zsigmond, H. Yang, Appl. Catal., A 2003, 256, 69-76.
65. X. Fang, T. M. Anderson, C. L. Hill, Angew. Chem. Int. Ed, 2005, 44, 3540-3544.
66. M. McCann, K. Maddock, Polyhedron 1994, 13, 3153-3158.
67. C. Jahier, S. Nlate, M. Cantuel, N. D. McClenaghan, T. Buffeteau, D. Cavagnat, F. Agbossou, M. Carraro, M. Bonchio, Chem. Eur. J. 2009, 15, 8703-8708.
68. C. R. Mayer, P. Herson, R. Thouvenot, Inorg. Chem. 1999, 38, 6152-6158.
69. Although great effort has been made in growing single crystals of the title complexes, good-quality single crystals have not yet been obtained.
70. J. Crassous, Chem. Soc. Rev. 2009, 38, 830-845 and references cited therein.
71. G. Lenoble, B. Hasenknopf, R. Thouvenot, J. Am. Chem. Soc. 2006, 128, 5735-5744.
72. a) F. B. Xin, M. T. Pope, J. Am. Chem. Soc. 1996, 118, 7731-7736;
73. b) R. Acerete, J. Server-Carrió, J. Am. Chem. Soc. 1990, 112, 9386-9387.
74. 183W NMR spectroscopic data.
75. E. Papaconstantinou, A. Mylonas, Polyhedron 1996, 15, 3211-3217.
76. E. Murguly, T. B. Norsten, N. R. Branda, Angew. Chem. Int. Ed. 2001, 40, 1752-1755.
77. Product 6 was thoroughly washed, with water and diethyl ether.
78. 183W NMR spectra.
79. J. Server-Carrió, J. Bas-Serra, M. E. Gonzalez-Nuñez, A. Garcia-Gastaldi, G. B. Jameson, L. C. W. Baker, R. Acerete, J. Am. Chem. Soc 1999, 121, 977-984.
80. A. Sartorel, M. Carraro, A. Bagno, G. Scorrano, M. Bonchio, J. Phys. Org. Chem. 2008, 21, 596-602.
81. S. Berardi, M. Bonchio, M. Carraro, V. Conte, A. Sartorel, G. Scorrano, J. Org. Chem. 2007, 72, 8954-8957.
82. 2 decomposition pathways.
83. S. Monge, X. Zhang, O. Giani, J.-J. Robin, React. Funct. Polym. 2009, 69, 380-384.
84. a) J. Canny, A. Tezè, R. Thouvenot, G. Hervé, Inorg. Chem. 1986, 25, 2114-2119;
85. b) N. H. Nsouli, B. S. Bassil, M. H. Dickman, U. Kortz, B. Keita, L. Nadjo, Inorg. Chem. 2006, 45, 3858-3860.
86. G. te Velde, F. M. Bickelhaupt, E. J. Baerends, C. Fonseca Guerra, S. J. A. van Gisbergen, J. G. Snijders, T. Ziegler, J. Comput. Chem. 2001, 22, 931-967.
87. a) S. K. Wolff, T. Ziegler, E. van. Lenthe, E. J. Baerends, J. ' Chem. Phys. 1999, 110, 7689-7698;
88. b) J. Autschbach in Calculation of NMR and EPR Parameters (Eds.: M. Kaupp, M. Bühl, VG. Malkin), Wiley-VCH, Weinheim, 2004, ch. 14;
89. E. van Lenthe, E. J. Baerends, J. G. Snijders, J. Chem. Phys. 1993, 99, 4597-4610;
90. E. van Lenthe, PhD Thesis, Vrije Universiteit, Amsterdam, the Netherlands, 1996.
91. a) A. D. Becke, Phys. Rev. A 1988, 38, 3098-3100;
92. b) J. P. Perdew, Phys. Rev. B 1986, 33, 8822-8824.
93. C. C. Pye, T. Ziegler, Theor. Chem. Acc. 1999, 101, 396-408.
94. a) A. Klamt, G. Schüürmann, J. Chem. Soc. Perkin Trans. 2 1993, 799-805;
95. b) A. Klamt, V. Jones, J. Chem. Phys. 1996, 105, 9972-9981;
96. A. Klamt, J. Phys. Chem. 1995, 99, 2224-2235.