Diffusion and NOE NMR studies on multicationic DAB-organoruthenium dendrimers: Size-dependent noncovalent self-assembly to megamers and ion pairing

Chemistry - A European Journal

Volumn 15, Issue 21, 2009, Pages 5337-5347

  Pettirossi, Stefania ^a   Bellachioma, Gianfranco ^a   Ciancaleoni, Gianluca ^a   Zuccaccia, Cristiano ^a   Zuccaccia, Daniele ^a   Macchioni, Alceo ^a  

^a UNIVERSITY OF PERUGIA   (Italy)

Author keywords

Dendrimers; Ion pairs; NMR spectroscopy; Ruthenium; Self assembly

Indexed keywords

CARBONYLDIIMIDAZOLE; CONCENTRATION OF; COUNTERION; DENDRIMER GENERATION; DIFFUSION NMR; DILUTE SOLUTION; FREE IONS; HETERONUCLEAR; ION PAIRING; ION PAIRS; MEGAMERS; METAL CENTERS; MULTINUCLEAR NMR; NMR SPECTROSCOPY; NMR STUDIES; NONCOVALENT; OVERHAUSER EFFECT; P-CYMENE; PYRIDYL; RELATIVE ANIONS; SUPRAMOLECULAR ASSEMBLIES; SUPRAMOLECULAR STRUCTURE; XRD;

DIFFUSION; EXPERIMENTS; IONS; KETONES; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLIGOMERS; RUTHENIUM; SELF ASSEMBLY; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS (CHEMICAL);

DENDRIMERS;

EID: 66249127588     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200802585     Document Type: Article

References (87)

1. C. Gorman, Adv. Mater. 1998, 10, 295
2. M. A. Hearshaw, J. R. Moss, Chem. Commun. 1999, 1
3. G. R. Newkome, E. He, C. N. Moorefield, Chem. Rev. 1999, 99, 1689
4. D. Astruc, J.-C. Blais, E. Cloutet, L. Djakovitch, S. Rigaut, J. Ruiz, V. Sartor, C. Valerio, Top. Curr. Chem. 2000, 210, 229
5. K. Onitsuka, S. Takahashi, Top. Curr. Chem. 2003, 228, 39
6. S.-H. Shreiner, C. D. Moorefield, G. R. Newkome, New J. Chem. 2007, 31, 1192
7. D. Astruc, C. Ornelas, J. Ruiz, Acc. Chem. Res. 2008, 41, 841.
8. R. van Heerbeek, P. C. J. Kamer, P. W. N. M. van Leeuwen, J. N. L. Reek, Chem. Rev. 2002, 102, 3717
9. D. Astruc, F. Chardac, Chem. Rev. 2001, 101, 2991
10. G. E. Oosterom, J. N. H. Reek, P. C. J. Kamer, P. W. N. M. van Leeuwen, Angew. Chem. 2001, 113, 1878
11. Angew. Chem. Int. Ed. 2001, 40, 1828
12. G. vanKoten, J. T. B. H. Jastrzebski, J. Mol. Catal. A 1999, 146, 317
13. R. Kreiter, A. W. Kleij, R. Gebbink, J. M. van Koten, Top. Curr. Chem. 2001, 217, 163
14. J. N. H. Reek, D. de Groot, G. E. Oosterom, P. C. J. Kamer, P. W. N. M. van Leeuwen, C.R. Chim. 2003, 6, 1061
15. P. A. Chase, R.J.M. Klein Gebbink, G. van Koten, J. Organomet. Chem. 2004, 689, 4016
16. Dendrimer Catalysis: Top. Organomet. Chem., Vol. 20, (Ed.: L. H. Gade), Springer, Berlin, 2006
17. M. Martin, F. Manea, R. Fiammengo, L.J. Prins, L. Pasquato, P. Scrimin, J. Am. Chem. Soc. 2007, 129, 6982
18. J. K. Kas-sube, H. Wadepohl, L. H. Gade, Adv. Synth. Catal. 2008, 350, 1155.
19. B. Helms, J. M. Frechet, Adv. Synth. Catal. 2006, 348, 1125.
20. C. Ornelas, E. Boisselier, V. Martinez, I. Pianet, J. Ruiz Aranzaes, D. Astruc, Chem. Commun. 2004, 5093
21. P. Wang, C. N. Moorefield, K.-U. Jeong, S.-H. Hwang, S. Li, S. Z. D. Cheng, G. R. Newkome, J. Adv. Mater. 2008, 20, 1381
22. E. Boisselier, C. Ornelas, I. Pianet, J. R. Arazaes, D. Astruc, Chem. Eur. J. 2008, 14, 5577.
23. A. Macchioni, Chem. Rev. 2005, 105, 2039, and references therein
24. B Binotti, C. Carfagna, C. Zuccaccia, A. Macchioni, Chem. Commun. 2005, 92
25. A. Correa, L. Cavallo, J. Am. Chem. Soc. 2006, 128, 10952
26. G. L. Hamilton, E. J. Kang, M. Mba, F. D. Toste, Science 2007, 317, 496
27. J. A. S. Roberts, M.-C. Chen, A. M. Seyam, C. Zuc- caccia, N. G. Stahl, T. J. Marks, J. Am. Chem. Soc. 2007, 129, 12713
28. J. Lacour, D. Linder, Chem. Rec. 2007, 7, 275
29. B. Binotti, G. Bella-chioma, G. Cardaci, C. Carfagna, C. Zuccaccia, A. Macchioni, Chem. Eur. J. 2007, 13, 1570.
30. E. L. Hahn, Phys. Rev. 1950, 80, 580
31. E. O. Stejskal, J. E. Tanner, J. Chem. Phys. 1965, 42, 288
32. P. Stilbs, Prog. Nucl. Magn. Reson. Spec- trosc. 1987, 19, 1
33. W. S. Price, Concepts Magn. Reson. 1998, 10, 197
34. C. S. Johnson, Jr., Prog. Nucl. Magn. Reson. Spectrosc. 1999, 34, 203.
35. Reviews of the application of diffusion NMR to investigate intermo-lecular interactions: B. Binotti, A. Macchioni, C. Zuccaccia, D. Zuc- caccia, Comments Inorg. Chem. 2002, 23, 417
36. P. S. Pregosin, E. Mar- tinez-Viviente, P. G. A. Kumar, Dalton Trans. 2003, 4007
37. A. Bagno, F. Rastrelli, G. Sacelli, Prog. Nucl. Magn. Reson. Spectrosc. 2005, 47, 41
38. T. Brand, E. J. Cabrata, S. Berger, Prog. Nucl. Magn. Reson. Spectrosc. 2006, 48, 159
39. Y. Cohen, L. Avram, L. Frish, Angew. Chem. 2005, 117, 524
40. Angew. Chem. Int. Ed. 2005, 44, 520
41. P. S. Pre-gosin, P. G. A. Kumar, I. Fernandez, Chem. Rev. 2005, 105, 2977
42. P. S. Pregosin, Prog. Nucl. Magn. Reson. Spectrosc. 2006, 49, 261
43. A. Pastor, E. Martinez-Viviente, Coord. Chem. Rev. 2008, 252, 2314.
44. The Nuclear Overhauser Effect in Structural and Conformational Analysis, 2nd ed., (Eds.: D. Neuhaus, M. Williamson) Wiley-VCH, Weinheim, 2000.
45. [9] A. Macchioni, Eur. J. Inorg. Chem. 2003, 195, and references therein.
46. G. Bellachioma, G. Ciancaleoni, C. Zuccaccia, D. Zuccaccia, A. Macchioni, Coord. Chem. Rev. 2008, 252, 2224, and references therein.
47. Ion triples: D. Zuccaccia, E. Foresti, S. Pettirossi, P. Sabatino, C. Zuccaccia, A. Macchioni, Organometallics 2007, 26, 6099.
48. Bications: S. Bolan&tild;o, G. Ciancaleoni, J. Bravo, L. Gonsalvi, A. Macchioni, M. Peruzzini, Organometallics 2008, 27, 1649.
49. Nanoaggregates: A. Macchioni, A. Romani, C. Zuccaccia, G. Gu- glielmetti, C. Querci, Organometallics 2003, 22, 1526
50. D. Zuccaccia, E. Clot, A. Macchioni, New J. Chem. 2005, 29, 430
51. G. Ciancaleoni, I. Di Maio, D. Zuccaccia, A. Macchioni, Organometallics 2007, 26, 489
52. R. van de Coevering, A. P. Alfers, J. D. Meeldijk, E. Martinez- Viviente, P. S. Pregosin, R. J. M. Klein Gebbink, G. van Koten, J. Am. Chem. Soc. 2006, 128, 12700.
53. Ion quadruples: S. Beck, A. Geyer, H.-H. Brintzinger, Chem. Commun. 1999, 2477
54. C. Zuccaccia, N. G. Stahl, A. Macchioni, M.-C. Chen, J. A. Roberts, T. J. Marks, J. Am. Chem. Soc. 2004, 126, 1448
55. F. Song, S. J. Lancaster, R. D. Cannon, M. Schormann, S. M. Humphrey, C. Zuccaccia, A. Macchioni, M. Bochmann, Organome- tallics 2005, 24, 1315
56. C. Alonso-Moreno, S. J. Lancaster, C. Zuccac- cia, A. Macchioni, M. Bochmann, J. Am. Chem. Soc. 2007, 129, 9282
57. D. Zuccaccia, G. Bellachioma, G. Cardaci, G. Ciancaleoni, C. Zuccaccia, E. Clot, A. Macchioni, Organometallics 2007, 26, 3930
58. L. Rocchigiani, C. Zuccaccia, D. Zuccaccia, A. Macchioni, Chem. Eur. J. 2008, 14, 6589
59. C. Alonso-Moreno, S. J. Lancaster, J. A. Wright, D. L. Hughes, C. Zuccaccia, A. Correa, A. Macchioni, L. Cavallo, M. Bochmann, Organometallics 2008, 27, 5474.
60. D. A. Tomalia, S. Uppuluri, D. R. Swanson, J. Li, Pure Appl. Chem. 2000, 72, 2343.
61. L. Busetto, M. C. Cassani, P. W. N. M. van Leeuwen, R. Mazzoni, Dalton Trans. 2004, 2767.
62. D. Zuccaccia, A. Macchioni, Organometallics 2005, 24, 3476; A. Macchioni, G. Ciancaleoni, C. Zuccaccia, D. Zuccaccia, Chem. Soc. Rev. 2008, 37, 479.
63. D. Zuccaccia, L. Pirondini, R. Pinalli, E. Dalcanale, A. Macchioni, J. Am. Chem. Soc. 2005, 127, 7025
64. H. Kang, A. Facchetti, P. Zhu, H. Jiang, Y. Yang, E. Cariati, S. Righetto, R. Ugo, C. Zuccaccia, A. Macchioni, C. L. Stern, Z. Liu, S.-T. Ho, T. J. Marks, Angew. Chem. 2005, 117, 8136
65. Angew. Chem. Int. Ed. 2005, 44, 7922
66. E. Menozzi, M. Busi, C. Massera, F. Ugozzoli, D. Zuccaccia, A. Macchioni, E. Dalcanale, J. Org. Chem. 2006, 71, 2617.
67. D. Zuccaccia, L. Busetto, M. C. Cassani, A. Macchioni, R. Mazzoni, Organometallics 2006, 25, 2201.
68. M. Chai, Y. Niu, W. J. Youngs, P. L. Rinaldi, J. Am. Chem. Soc. 2001, 123, 4670.
69. R. Romeo, N. Nastasi, L. Monsu` Scolaro, M. R. Plutino, A. Albinati, A. Macchioni, Inorg. Chem. 1998, 37, 5460; K. Wichmann, B. Anto-nioli, T. So¨hnel, M. Wenzel, K. Gloe, K. Gloe, J. R. Price, L. F. Lindoy, A.J. Blake, M. Schro¨der, Coord. Chem. Rev. 2006, 250, 2987, and references therein.
70. Studies where N has been used: S. S. Pochapsky, H. Mo, T. Pochap- sky, J. Chem. Soc. Chem. Commun. 1995, 2513
71. H. Mo, T. Pochap-sky, J. Phys. Chem. B 1997, 101, 4485
72. C. Zuccaccia, G. Bellachioma, G. Cardaci, A. Macchioni, Organometallics 2000, 19, 4663.
73. G. Ciancaleoni, C. Zuccaccia, D. Zuccaccia, A. Macchioni, Organo-metallics 2007, 26, 3624.
74. Y. Marcus, G. Hefter, Chem. Rev. 2006, 106, 4585.
75. E. Murugan, R. L. Sherman, Jr., H. O. Spivey, W. T. Ford, Langmuir 2004, 20, 8307
76. N. O. Mchedlov-Petrossyan, E. Y. Bryleva, N. A. Vo-dolazkaya, A. A. Dissanayake, W. T. Ford, Langmuir 2008, 24, 5689.
77. C. Schmuck, Coord. Chem. Rev. 2006, 250, 3053.
78. J. Jeener, B. H. Meier, P. Bachmann, R. R. Ernst, J. Chem. Phys. 1979, 71, 4546.
79. R. Wagner, S. Berger, J. Magn. Reson. Ser. A 1996, 123, 119.
80. B. Lix, F. D. Sonnichsen, B. D. Sykes, J. Magn. Reson. Ser. A 1996, 121, 83.
81. M. Valentini, H. Ruegger, P. S. Pregosin, Helv. Chim. Acta 2001, 84, 2833, and references therein.
82. H. J. W. Tyrrell, K. R. Harris, Diffusion in Liquids, Butterworth, London, 1984 ; R. Mills, J. Phys. Chem. 1973, 77, 685.
83. N. J. A. Sloane, with the collaboration of R. H. Hardin, W. D. Smith and others, Tables of Spherical Codes, http://www.research.att. com/ ∼ njas/packings/
84. R. H. Blessing, Acta Crystallogr. Sect. A 1995, 51, 33.
85. A. Altomare, M. C. Burla, M. Camalli, G. Cascarano, C. Giacovaz- zo, A. Gagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna, J. Appl. Crystallogr. 1999, 32, 115.
86. G. M. Sheldrick, SHELXL-97, A program for crystal structure refinement, Release 92-92, University of Goettingen, Germany, 1997.
87. [36] L. Farrugia, J. Appl. Crystallogr. 1999, 32, 837.