Probing stepwise complexation in phenylazomethine dendrimers by a metallo-porphyrin core

Journal of the American Chemical Society

Volumn 127, Issue 40, 2005, Pages 13896-13905

  Imaoka, Takane ^a   Tanaka, Reiko ^a   Arimoto, Sachiko ^a   Sakai, Makoto ^b   Fujii, Masaaki ^b   Yamamoto, Kimihisa ^a  

^a KEIO UNIVERSITY   (Japan)

^b Tokyo Institute of Technology ^*  (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION SPECTROSCOPY; CHROMATOGRAPHIC ANALYSIS; COMPLEXATION; CYCLIC VOLTAMMETRY; ELECTRON MICROSCOPY; FLUORESCENCE; IONS; ORGANOMETALLICS; PORPHYRINS; REDOX REACTIONS; RELAXATION PROCESSES; TITRATION;

CYCLIC VOLTAMMOGRAMS; DENDRITIC PHENYLAZOMETHINES (DPA); METAL COMPLEXES; TUNNELLING ELECTRON MICROSCOPY;

DENDRIMERS;

AZO COMPOUND; BENZENE DERIVATIVE; DENDRIMER; FERRIC CHLORIDE; IMINE; METAL COMPLEX; METAL ION; METALLOPORPHYRIN; TIN CHLORIDE; ZINC DERIVATIVE;

ABSORPTION SPECTROSCOPY; ARTICLE; CALCULATION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CYCLIC POTENTIOMETRY; ELECTRON TRANSPORT; FLUORESCENCE; GEL PERMEATION CHROMATOGRAPHY; MEASUREMENT; MOLECULAR MODEL; OXIDATION REDUCTION REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTITATIVE ANALYSIS; REACTION ANALYSIS; SYNTHESIS; TITRIMETRY; TRANSMISSION ELECTRON MICROSCOPY; ULTRAVIOLET SPECTROSCOPY; VISCOSITY;

AZO COMPOUNDS; CRYSTALLOGRAPHY, X-RAY; DENDRIMERS; ELECTROCHEMISTRY; FLUORESCENT DYES; METALLOPORPHYRINS; MICROSCOPY, FLUORESCENCE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PORPHYRINS; SPECTROPHOTOMETRY, ULTRAVIOLET; ZINC;

EID: 26444481979     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0524797     Document Type: Article

References (98)

1. A synthetic macromolecules with no structural dispersion. For selected reviews, see: (a) Tomalia, D. A.; Naylor, A. M.; Goddard, W. A., III. Angew. Chem., Int. Ed. Engl. 1990, 29, 138-175.
2. (b) Zeng, F.; Zimmerman, S. C. Chem. Rev. 1997, 97, 1681-1712.
3. (c) Fischer, M.; Vögtle, F. Angew. Chem., Int. Ed. 1999, 38, 885-905.
4. (d) Majoral, J.-P.; Caminade, A.-M. Chem. Rev. 1999, 99, 845-880.
5. (e) Bosman, A. W.; Janssen, H. M.; Meijer, E. W. Chem. Rev. 1999, 99, 1665-1688.
6. (f) Vögtle, F.; Gestermann, S.; Hesse, R.; Schwierz, H.; Windisch, B. Prog. Polym. Sci. 2000, 25, 987-1041.
7. (g) Hecht, S.; Fréchet, J. M. J. Angew. Chem., Int. Ed. 2001, 40, 74-91.
8. (h) Fréchet, J. M. J.; Tomalia, D. A. Dendrimers and other Dendritic Polymers; John Wiley & Sons: New York, 2002.
9. (i) Newkome, G. R.; Moorefield, C. N.; Vögtle, F. Dendrimers and Dendrons: Concepts, Synthesis, Applications; Wiley-VCH: Weinheim, 2001.
10. Macromolecule-metal Complexes; Ciardelli, F., Tsuchida, F., Wohrle, D., Eds.; Springer: New York, 1996.
11. Many dendrimers containing metal complexes are reported. They can be seen in the following review: Newkome, G. R.; He, E.; Moorefield, C. N. Chem. Rev. 1999, 99, 1689-1746.
12. (a) Bhyrappa, P.; Young, J. K.; Moore, J. S.; Suslick, K. S. J. Am. Chem. Soc. 1996, 118, 5708-5711.
13. (b) Kimura, M.; Shiba, T.; Yamazaki, M.; Hanabusa, K.; Shirai, H.; Kobayashi, N. J. Am. Chem. Soc. 1999, 121, 5636-5642.
14. (c) Uyemura, M.; Aida, T. J. Am. Chem. Soc. 2002, 124, 11392-11403.
15. (d) Uyemura, M.; Aida, T. Chem.-Eur. J. 2003, 9, 3492-3500.
16. (a) Brunner, H. J. Organomet. Chem. 1995, 500, 39-46.
17. (b) Chow, H.-F.; Mak, C. C. J. Org. Chem. 1997, 62, 5116-5127.
18. (c) Rheiner, P. B.; Seebach, D. Chem.-Eur. J. 1999, 5, 3221-3236.
19. (d) Kimura, M.; Sugihara, Y.; Muto, T.; Hanabusa, K.; Shirai, H.; Kobayashi, N. Chem.-Eur. J. 1999, 5, 3495-3500.
20. (e) Sen, A.; Suslick, K. S. J. Am. Chem. Soc. 2000, 122, 11565-11566.
21. (f) Hecht, S.; Fréchet, J. M. J. J. Am. Chem. Soc. 2001, 123, 6959-6960.
22. (g) Astruc, D.; Chardac, F. Chem. Rev. 2001, 101, 2991-3023.
23. (h) Twyman, L. J.; King, A. S. H.; Martin, I. K. Chem. Soc. Rev. 2002, 31, 69-82.
24. (a) Valério, C.; Alonso, E.; Ruiz, J.; Blais, J.-C.; Astruc, D. Angew. Chem., Int. Ed. 1999, 38, 1747-1751.
25. (b) Daniel, M.-C.; Ruiz, J.; Blais, J.-C.; Daro, N.; Astruc, D. Chem.-Eur. J. 2003, 9, 4371-4379.
26. (c) Valério, C.; Fillaut, J.-L.; Ruiz, J.; Guittard, J.; Blais, J.-C.; Astruc, D. J. Am. Chem. Soc. 1997, 119, 2588-2589.
27. (d) Daniel, M.-C.; Ruiz, J.; Nlate, S.; Blais, J.-C.; Astruc, D. J. Am. Chem. Soc. 2003, 125, 2617-2628.
28. (a) Crooks, R. M.; Zhao, M.; Sun, L.; Chechik, V.; Yeung, L. K. Acc. Chem. Res. 2001, 34, 181-190.
29. (b) Zhao, M.; Crooks, R. M. Adv. Mater. 1999, 11, 217-220.
30. (c) Zhao, M.; Crooks, R. M. Angew. Chem., Int. Ed. 1999, 38, 364-366.
31. (d) Zhao, M.; Sun, L.; Crooks, R. M. J. Am. Chem. Soc. 1998, 120, 4877-4878.
32. (e) Chechik, V.; Crooks, R. M. J. Am. Chem. Soc. 2000, 122, 1243-1244.
33. (f) Lang, H.; May, R. A.; Iversen, B. L.; Chandler, B. D. J. Am. Chem. Soc. 2003, 125, 14832-14836.
34. (g) Ooe, M.; Murata, M.; Mizugaki, T.; Ebitani, K.; Kaneda, K. J. Am. Chem. Soc. 2004, 126, 1604-1605.
35. (h) Balogh, L.; Tomalia, D. A. J. Am. Chem. Soc. 1998, 120, 7355-7356.
36. (a) Yamamoto, K.; Higuchi, M.; Shiki, S.; Tsuruta, M.; Chiba, H. Nature 2002, 415, 509-511.
37. (b) Imaoka, T.; Horiguthi, H.; Yamamoto, K. J. Am. Chem. Soc. 2003, 125, 340-341.
38. (c) Enoki, O.; Imaoka, T.; Yamamoto, K. Org. Lett. 2003, 5, 2547-2549.
39. (d) Satoh, N.; Cho, J.-S.; Higuchi, M.; Yamamoto, K. J. Am. Chem. Soc. 2003, 125, 8104-8105.
40. (e) Higuchi, M.; Tsuruta, M.; Chiba, H.; Shiki, S.; Yamamoto, K. J. Am. Chem. Soc. 2003, 125, 9988-9997.
41. (f) Yamamoto, K.; Higuchi, M.; Kimoto, A.; Imaoka, T.; Masachika, K. Bull. Chem. Soc. Jpn. 2005, 78, 349-355.
42. (a) Tominaga, M.; Hosogi, J.; Konishi, K.; Aida, T. Chem. Commun. 2000, 719-720.
43. (b) Klein Gebbink, R. J. M.; Bosman, A. W.; Feiters, M. C.; Meijer, E. W.; Nolte, R. J. M. Chem.-Eur. J. 1999, 5, 65-69.
44. (c) Ottaviani, M. F.; Montalti, F.; Turro, N. J.; Tomalia, D. A. J. Phys. Chem. B 1997, 101, 158-166.
45. (d) Ottaviani, M. F.; Bossmann, S.; Turro, N. J.; Tomalia, D. A. J. Am. Chem. Soc. 1994, 116, 661-671.
46. (e) Vogue, F.; Gestermann, S.; Kauffmann, C.; Ceroni, P.; Vicinelli, V.; Balzani, V. J. Am. Chem. Soc. 2000, 122, 10398-10404.
47. (f) Vicinelli, V.; Ceroni, P.; Maestri, M.; Balzani, V.; Gorka, M.; Vögtle, F. J. Am. Chem. Soc. 2002, 124, 6461-6468.
48. (g) Cohen, S. M.; Petoud, S.; Raymond, K. N. Chem.-Eur. J. 2001, 7, 272-279.
49. (h) Grabchev, I.; Chovelon, J.-M.; Qian, X. New J. Chem. 2003, 27, 337-340.
50. The description is mainly noted in the Supporting Information of ref 8b.
51. Bettelheim, A.; White, B. A.; Raybuck, S. A.; Murray, R. W. Inorg. Chem. 1987, 26, 1009-1017.
52. Takanashi, K.; Chiba, H.; Higuchi, M.; Yamamoto, K. Org. Lett. 2004, 6, 1709-1712.
53. Fréchet, J. M. J. Science 1994, 263, 1710-1715.
54. The fluorescence of the titanyl porphyrin appeared around 600 nm upon an excitation at 540 nm (porphyrin Q-band), while the free-base porphyrin showed a fluorescence around 650 nm.
55. Tomoyose, Y.; Jiang, D.-L.; Jin, R.-H.; Aida, T.; Yamashita, T.; Horie, K.; Yashima, E.; Okamoto, Y. Macromolecules 1996, 29, 5236-5328.
56. Bahary, W. S.; Hogan, N. P.; Jilani, M.; Aronson, M. P. In Advances in Chemistry Series; Chromatographic Characterization of Polymers; Provder, T., Barth, H. G., Urban, M. W., Eds.; American Chemical Society: Washington, DC, 1995; Vol. 247, pp 151-166.
57. Billmeyer, F. W., Jr. Textbook of Polymer Science, 3rd ed.; John Wiley & Sons: New York, 1984; p 208.
58. Matos, M. S.; Hofkens, J.; Verheijen, W.; De Schryver, F. C.; Hecht, S.; Pollak, K. W.; Fréchet, J. M. J.; Forier, B.; Dehaen, W. Macromolecules 2000, 33, 2967-2973.
59. (a) Boris, D.; Rubinstein, M. Macromolecules 1996, 29, 7251-7260.
60. (b) Cavallo, L.; Fraternali, F. Chem.-Eur. J. 1998, 4, 927-934.
61. (c) Ballauff, M.; Likos, C. N. Angew. Chem., Int. Ed. 2004, 43, 2998-3020.
62. (a) Cardona, C. M.; Kaifer, A. E. J. Am. Chem. Soc. 1998, 120, 4023-4024.
63. (b) Gorman, C. B.; Smith, J. C.; Hager, M. W.; Parkhurst, B. L.; Sierzputowska-Gracz, H.; Haney, C. A. J. Am. Chem. Soc. 1999, 121, 9958-9966.
64. (c) Goldsmith, J. I.; Takada, K.; Abruña, H. D. J. Phys. Chem. B 2002, 106, 8504-8513.
65. Higuchi, M.; Shiki, S.; Ariga, K.; Yamamoto, K. J. Am. Chem. Soc. 2001, 123, 4414-4420.
66. Hecht, S.; Vladimirov, N.; Fréchet, J. M. J. J. Am. Chem. Soc. 2001, 123, 18-25.
67. (a) Dandliker, P. J.; Diederich, F.; Gross, M.; Knobler, C. B.; Louati, A.; Sanford, E. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1739-1742.
68. (b) Pollak, K. W.; Leon, J. W.; Fréchet, J. M. J.; Maskus, M.; Abruña, H. D. Chem. Mater. 1998, 10, 30-38.
69. (c) Weyermann, P.; Gisselbrecht, J.-P.; Boudon, C.; Diederich, F.; Gross, M. Angew. Chem., Int. Ed. 1999, 38, 3215-3219.
70. (d) Gorman, C. B.; Smith, J. C. Acc. Chem. Res. 2001, 34, 60-71.
71. (e) Chasse, T. L.; Sachdeva, R.; Li, Q.; Li, Z.; Petrie, R. J.; Gorman, C. B. J. Am. Chem. Soc. 2003, 125, 8250-8254.
72. Nicholson, R. S. Anal. Chem. 1965, 37, 1351-1355.
73. Hecht, S.; Fréchet, J. M. J. J. Am. Chem. Soc. 1999, 121, 4084-4085.
74. Traficante, D. D. In Encyclopedia of Nuclear Magnetic Resonance; Grant, D. M., Harris, R. K., Eds.; John Wiley: New York, 1996; Vol. 6, pp 3988-4003.
75. -1 L], the fitting of the titration curve was successful. In contrast, we could not fit the titration curve using the equally coordinating system, in which the metal ions coordinate to all ligands with the same constant.
76. Nakajima, R.; Tsuruta, M.; Higuchi, M.; Yamamoto, K. J. Am. Chem. Soc. 2004, 126, 1630-1631.
77. Boulas, P. L.; Gómez-Kaifer, M.; Echegoyen, L. Angew. Chem., Int. Ed. 1998, 37, 216-247.
78. The main reason for the environmental change should be switching of the entire conformation of the dendrimer through the complexation. It can be observed as the change in the molecular size by DLS (dynamic light scattering) measurements (in Supporting Information).
79. (a) Maus, M.; De, R.; Lor, M.; Weil, T.; Mitra, S.; Wiesler, U.-M.; Herrmann, A.; Hofkens, J.; Vosch, T.; Müllen, K.; De Schryver, F. C. J. Am. Chem. Soc. 2001, 123, 7768-7676.
80. (b) Varnavski, O. P.; Ostrowski, J. C.; Sukhomlinova, L.; Twieg, R. J.; Bazan, G. C.; Goodson, T., III. J. Am. Chem. Soc. 2002, 124, 1736-1743.
81. (c) Ranasinghe, M. I.; Wang, Y.; Goodson, T., III. J. Am. Chem. Soc. 2003, 125, 5258-5259.
82. (d) Wang, Y.; Ranasinghe, M. I.; Goodson, T., III. J. Am. Chem. Soc. 2003, 125, 9562-9563.
83. (a) Choi, M.-S.; Aida, T.; Luo, H.; Araki, Y.; Ito, O. Angew. Chem., Int. Ed. 2003, 42, 4060-4063.
84. (b) Ghaddar, T. H.; Wishart, J. F.; Thompson, D. W.; Whitesell, J. K.; Fox, M. A. J. Am. Chem. Soc. 2002, 124, 8285-8289.
85. (c) Lor, M.; Thielemans, J.; Viaene, L.; Cotlet, M.; Hofkens, J.; Weil, T.; Hampel, C.; Müllen, K.; Verhoeven, J. W.; Van der Auweraer, M.; De Schryver, F. C. J. Am. Chem. Soc. 2002, 124, 9918-9925.
86. No significant absorption band appears in the region of a wavelength longer than the fluorescence band of the zinc porphyrin core (616 nm).
87. (a) Kalyanasundaram, K. Photochemistry of Polypyridine and Porphyrin Complexes; Academic Press: London, 1992.
88. (b) Da Ros, T.; Prato, M.; Guldi, D. M.; Alessio, E.; Ruzzi, M.; Pasimeni, L. Chem. Commun. 1999, 635-636.
89. (c) Luo, C.; Imahori, H.; Tamaki, K.; Sakata, Y. J. Am. Chem. Soc. 2000, 122, 6535-6551.
90. The fluorescence lifetimes of DPAGX-ZnP (X = 1-4) were determined to be 1.8 ns (G1), 2.1 ns (G2), 2.2 ns (G3), and 2.3 ns (G4).
91. Rodriguez, J.; Kirmaier, C.; Holten, D. J. Am. Chem. Soc. 1989, 111, 6500-6506.
92. (a) Goodson, T., III. Acc. Chem. Res. 2005, 38, 99-107.
93. (b) Goodson, T., III. Annu. Rev. Phys. Chem. 2005, 56, 581-603.
94. Yu, H.-Z.; Baskin, S.; Steiger, B.; Anson, F. C.; Zewail, A. H. J. Am. Chem. Soc. 1999, 121, 484-485.
95. Trent, J. S.; Scheinbeim, J. I.; Couchman, P. R. Macromolecules 1983, 16, 589-598.
96. Pavilishchuk, V. V.; Addison, A. W. Inorg. Chim. Acta 2000, 298, 97-102.
97. (a) Sakai, M.; Ishiuchi, S.; Fujii, M. Eur. Phys. J. D 2002, 20, 399-402.
98. (b) Sakai, M.; Fujii, M. Chem. Phys. Lett. 2004, 396, 298-302.