Assembly of a tetrathiafulvalene-anthracene dyad on the surfaces of gold nanoparticles: Tuning the excited-state properties of the anthracene unit in the dyad

Chemistry - A European Journal

Volumn 12, Issue 4, 2006, Pages 1067-1073

  Zhang, Guanxin ^a,b   Zhang, Deqing ^a   Zhao, Xiaohui ^a,b   Ai, Xicheng ^a   Zhang, Jianping ^a   Zhu, Daoben ^a  

^a INSTITUTE OF CHEMISTRY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

Anthracene; Electron transfer; Gold; Nanostructures; Self assembly; Tetrathiafulvalene

Indexed keywords

ABSORPTION; COMPLEXATION; DIMERIZATION; ELECTRONS; FLUORESCENCE; NANOSTRUCTURED MATERIALS; SELF ASSEMBLY;

ANTHRACENE; ELECTRON TRANSFER; NANOSTRUCTURES; TETRATHIAFULVALENE;

GOLD;

EID: 31344436970     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200500524     Document Type: Article

References (94)

1. a) J. M. Williams, J. R. Ferraro, R. J. Thorn, K. D. Carlson, U. Geiser, H. H. Wang, A. M. Kini, M. H. Whangbo, Organic Superconductors (Including Fullerenes), Prentice Hall, Englewood Cliffs, NJ, 1992;
2. b) J.-P. Farges, Organic Conductors. Fundamentals and Applications, Marcel Dekker, NY, 1994.
3. a) M. R. Bryce, Adv. Mater. 1999, 11, 11-23 and references therein;
4. b) J. L. Segura, N. Martín, Angew. Chem. 2001, 113, 1416-1455;
5. Angrew. Chem. Int. Ed. 2001, 40, 1372-1409, and references therein.
6. See for example, a) M. B. Nielsen, J. G. Hansen, J. Becher, Eur. J. Org. Chem. 1999, 2807-2815;
7. b) J. G. Hansen, K. S. Bang, N. Thorup, J. Becher, Eur. J. Org. Chem. 2000, 2135-2144;
8. c) K. B. Simonsen, K. Zong, R. D. Rogers, M. P. Cava, J. Becher, J. Org. Chem. 1997, 62, 679-686;
9. d) K. B. Simonsen, N. Thorup, M. P. Cava, J. Becher. Chem. Commun. 1998, 901-902;
10. e) D. F. Perepichka, M. R. Bryce, E. J. L. McInnes, J. Zhao, Org. Lett. 2001, 3, 1431-1434;
11. f) R. M. Metzger, Acc. Chem. Res. 1999, 32, 950-957;
12. g) R. M. Metzger, B. Chen. U. Höpfner, M. V. Lakshmikantham, D. Vuillaume, T. Kawai, X. Wu, H. Tachibana, T. V. Hughes, H. Sakurai, J. W. Baldwin, C. Hosch, M. P. Cava, L. Brehmer, G. J. Ashwell, J. Am. Chem. Soc. 1997, 119, 10455-10466;
13. h) M. C. Dìaz, B. M. Illescas, N. Martín, R. Viruela, P. M. Viruela, E. Ortí. O. Brede, I. Zilbermann, D.M. Guldi, Chem. Eur. J. 2004, 10, 2067-2077;
14. i) F. Giacalone, J. L. Sogura, N. Martín. D. M. Guldi, J. Am. Chem. Soc. 2004, 126, 5340-5341;
15. j) N. Gautier, F. Dumur, V. Lloveras, J. V. Gancedo, J. Veciana, C. Rovira, P. Hudhomme, Angew. Chem. 2003, 115, 2871-2874;
16. Angew. Chem. Int. Ed. 2003, 42, 2765-2768;
17. k) F. Dumur, N. Gautier, N. Gallego-Planas, Y. Sahin, E. Levillain, N. Mercier, P. Hudhomme, M. Masino, A. Girlando, V. Lloveras, J. Vidal-Gancedo, J. Veciana, C. Rovira, J. Org. Chem. 2004, 69, 2164-2177.
18. See for example, a) A. R. Pease, J. O. Jeppesen, J. F. Stoddart, Y. Luo, C. P. Collier, J. R. Heath, Acc. Chem. Res. 2001, 34, 433-444, and references therein;
19. b) C. Farren, C. A. Christensen, S. FitzGerald, M. R. Bryce, A. Beeby, J. Org. Chem. 2002, 67, 9130-9139;
20. c) H. Li, J. O. Jeppesen, E. Levillain, J. Becher, Chem. Commun. 2003, 846-847;
21. d) J. O. Jeppesen, J. Perkins, J. Becher, J. F. Stoddart, Angew. Chem. 2001, 113, 1256-1261;
22. Angew. Chem. Int. Ed. 2001, 40, 1216-1221;
23. e) Y. Luo, C. Collier, J. Jeppesen, K. Nielsen, E. DeIonno, G. Ho, J. Perkins, H. Tseng, T. Yamamoto, J. F. Stoddart, J. Heath, ChemPhysChem 2002, 3, 519-525;
24. f) H. Tseng, S. Vignon, J. F. Stoddart, Angew. Chem. 2003, 115, 1529-1533;
25. Angew. Chem. Int. Ed. 2003, 42, 1491-1495;
26. g) H. Yu, Y. Luo, K. Beverly, J. F. Stoddart, H. Tseng, J. Heath, Angew. Chem. 2003, 115, 5884-5889;
27. Angew. Chem. Int. Ed. 2003, 42, 5706-5711;
28. h) J. Jeppesen, S. Vignon, J. F. Stoddart, Chem. Eur J. 2003, 9, 4611-4625;
29. i) J. Jeppesen, K. Nielsen, J. Perkins, S. Vignon, A. Fahio, R. Ballardini, M. Gandolfi, M. Venturi, V. Balzani, J. Becher, J. F. Stoddart, Chem. Eur. J. 2003, 9, 2982-3007;
30. j) Y. Liu, A. H. Flood, J. F. Stoddart, J. Am. Chem. Soc. 2004, 126, 9150-9151;
31. k) D. Steuerman, H. Tseng, A. Peters, A. Flood, J. Jeppesen, K. Nielsen, J. F. Stoddart, J. Heath, Angew. Chem. 2004, 116, 6648-6653;
32. Angew. Chem. Int. Ed. 2004, 43, 6486-6491;
33. l) A. Flood, A. Peters, S. Vignon, D. Steuerman, H. Tseng, S. Kang, J. Heath, J. F. Stoddart, Chem. Eur. J. 2004, 10, 6558-6564;
34. m) H.-R. Tseng, S. A. Vignon, P. C. Celestre, J. Perkins, J. O. Jeppesen, A. D. Fabio, R. Ballardini, M. T. Gandolfi, M. Venturi, V. Balzani, J. F. Stoddart, Chem. Eur. J. 2004, 10, 155-172;
35. n) S. Kang, S. Vignon, H. Tseng, J. F. Stoddart, Chem. Eur. J. 2004, 10, 2555-2564;
36. o) T. Huang, H. Tseng, L. Sha, W. Lu, B. Brough, A. H. Flood, B. Yu, P. C. Celestre, J. Chang, J. F. Stoddart, C. Ho, Nano Lett. 2004, 4, 2065-2071;
37. p) H. Tseng, D. Wu, N. Fang, X. Zhang, J. F. Stoddart, ChemPhysChem 2004, 111-116;
38. q) I. Lee, C. Frank, Langmuir 2004, 20, 5809-5828;
39. r) B. W. Laursen, S. Nygaard, J. O. Jeppesen, J. F. Stoddart, Org. Lett. 2004, 6, 4167-4170;
40. s) S. S. Jang, Y. H. Jang, Y.-H. Kim, W. A. Goddard, A. H. Flood, B. W. Laursen, H-R. Tseng, J. F. Stoddart, J. O. Jeppesen, J. W. Choi, D. W. Steuerman, E. DeIonno, J. R. Heath, J. Am. Chem. Soc. 2005, 127, 1563-1575;
41. t) M. Asakawa, P. R. Ashton, V. Balzani, A. Credi, G. Mattersteig, O. A. Matthews, M. Montalti, N. Spencer, J. F. Stoddart, M. Venturi, Chem. Eur. J. 1997, 3, 1992-1996.
42. G. Zhang, D. Zhang, X. Guo, D. Zhu, Org. Lett. 2004, 6, 1209-1212.
43. a) G. Zhang, X. Li, H. Ma, D. Zhang, J. Li, D. Zhu, Chem. Commun. 2004, 18, 2072-2073;
44. h) X. Li, G. Zhang, H. Ma, D. Zhang, J. Li, D. Zhu, J. Am. Chem. Soc. 2004, 126, 11543-11548.
45. See for example, a) M. C. Daniel, D. Astruc, Chem. Rev. 2004, 104, 293-346, and references therein;
46. b) K. G. Thomas, P. V. Kamat, Acc. Chem. Res. 2003, 36, 888-898, and references therein;
47. c) K. G. Thomas, B. I. Ipe, P. K. Sudeep, Pure Appl. Chem. 2002, 74, 1731-1738;
48. d) A. C. Templeton, W. P. Wuelfing, R. W. Murray, Acc. Chem. Res. 2000, 33, 27-36;
49. e) S. Chen, R. S. Ingram, M. J. Hostetler, J. J. Pietron, R. W. Murray, T. G. Schaaff, J. T. Khoury, M. M. Alvarez, R. L. Whetten, Science 1998, 280, 2098-2101;
50. f) M. J. Hostetler, S. J. Green, J. J. Stokes, R. W. Murray, J. Am. Chem. Soc. 1996, 118, 4212-4213;
51. g) R. S. Ingram, M.J. Hostetler, R. W. Murray, J. Am. Chem. Soc. 1997, 119, 9175-9178;
52. h) A. C. Templeton, M. J. Hostetler, C.T. Kraft, R.W. Murray, J. Am. Chem. Soc. 1998, 120, 1906-1911;
53. i) W. P. Wuelfing, S. J. Green, J. J. Pietron, D. E. Cliffel, R. W. Murray, J. Am. Chem. Soc. 2000, 122, 11465-11472;
54. j) J. F. Hicks, F. P. Zamborini, A. J. Osisck, R. W. Murray, J. Am. Chem. Soc. 2001, 123, 7048-7053;
55. k) F. P. Zamborini, M. C. Leopold, J. F. Hicks, P. J. Kulesza, M. A. Malik, R. W. Murray, J. Am. Chem. Soc. 2002, 124, 8958-8964;
56. l) Y. Song, R. W. Murray, J. Am. Chem. Soc. 2002, 124, 7096-7102;
57. m) D. Lee, R. L. Donkers, J. M. DeSimone, R. W. Murray, J. Am. Chem. Soc. 2003, 125, 1182-1183;
58. n) D. Leu, R. L. Donkers, G. Wang, A. S. Harper, R. W. Murray, J. Am. Chem. Soc. 2004, 126, 6193-6199;
59. o) G. Wang, T. Huang, R. W. Murray, L. Menard, R. G. Nuzzo, J. Am. Chem. Soc. 2005, 127, 812-813;
60. p) R. Guo, Y. Song, G. Wang, R. W. Murray, J. Am. Chem. Soc. 2005, 127, 2752-2757;
61. q) S. Chen, R. Pei, J. Am. Chem. Soc. 2001, 123, 10607-10615;
62. r) B. M. Quinn, P. Liljeroth, V. Ruiz, T. Laaksonen, K. Kontturi, J. Am. Chem. Soc. 2003, 125, 6644-6645;
63. s) T. Hasobe, H. Imahori, P. V. Kamat, S. Fukuzumi, J. Am. Chem. Soc. 2003, 125, 14962-14963;
64. t) T. Hasohe, H. Imahori, P. V. Kamat, T. K. Ahn. S. K. Kim, D. Kim, A. Fujimoto, T. Hirakawa, S. Fukuzumi, J. Am. Chem. Soc. 2005, 127, 1216-1228;
65. u) S. Barazzouk, P. V. Kamat, S. Hotchandani, J. Phys. Chem. B 2005, 109, 716-723;
66. v) H. Nakai, M. Yoshihara, H. Fujihara, Langmuir 1999, 15, 8574-8576.
67. a) B. I. Ipe, K. George Thomas, S. Barazzouk, S. Hotchandani, P. V. Kamat, J. Phys. Chem. B, 2002, 106, 18-21;
68. b) T. Wang, D. Zhang, W. Xu, J. Yang, R. Han, D. Zhu, Langmuir 2002, 18, 1840-1848.
69. P. V. Kamat, S. Barazzouk, S. Hotchandani, Angew, Chem. 2002, 114, 2888-2891;
70. Angew. Chem. Int. Ed. 2002, 41, 2764-2767.
71. K. G. Thomas, P. V. Kamat, J. Am. Chem. Soc. 2000, 122, 2655-2656.
72. a) X. M. Li, M. R. de Jone, K. Inoue, S. Shinkai, J. Huskens, D. N. Reinhoudt, J. Mater. Chem. 2001, 11, 1919-1923;
73. b) M. M. Maye, S. C. Chun, L. Han, D. Rabinovich, C. J. Zhong, J. Am. Chem. Soc. 2002, 124, 4958-4959;
74. c) E. J. Shelley, D. Ryan, S. R. Johnson, M. Couillard, D. Fitzmaurice, P. D. Nellist, Y. Chen, R. E. Palmer, J. A. Preece, Langmuir 2002, 18, 1791-1795.
75. Au = 0.145 nm) (see R. H. Terrill, T. A. Postlethwaite, C.-H Chen, C.-D. Poon, A Terzis, A. Chen, J. E. Hutchison, M. R. Clark, G. Wignall, J. G. Londono, R. Superfine, M. Falvo, C. S. Johnson, E. T. Samulski, R. W. Murray, J. Am. Chem. Soc. 1995, 117, 12537-12548;
76. M. J. Hostetler, S. J. Green, J. J. Stokes, R. W. Murray, J. Am. Chem. Soc. 1996, 118, 4212-4213;
77. R. S. Ingram, M. J. Hostetler, R. W. Murray, J. Am. Chem. Soc. 1997, 119, 9175-9178), the model predicts that the average core of the gold nanoparticles contains 3795 Au atoms, of which 968 lie on the surface. Based on the concentration and volume of dyad 1 and gold nanoparticles used in the respective studies, the number of dyad 1 molecules that lie on the surface of each nanopar tide on average can he estimated, if we assume that all molecules of dyad 1 are adsorbed. For spectral adsorption studies (gold nanopartides. 0.2 mL, 11 mM; dyad 1, 5 mL, 80 μM), the corresponding coverage ratio was calculated to be 73%.
78. a) U. Kreibig, M. Vollmer, Optical Properties of Metal Clusters, Springer, Berlin, 1995;
79. b) U. Kreibig, M. Gartz, A. Hilger, H. Hovel, In Fine Particles Science and Technology (Ed.: E.Pelizzatti, Kulwer Academic, Boston, 1996, pp. 499-516;
80. c) P. Mulvaney, In Semiconductor Nanoclusters-Physical, Chemical and Catalytic Aspects (Eds.: P. V. Kamat, D. Meisel) Elsevier Science, Amsterdam, 1997, pp. 99-123.
81. 2/εr=-0.1 eV; see a) D. Rehm, A. Weller, Isr. J. Chem. 1970, 8, 259-271;
82. PET shows that the photoinduced-electron- transfer process is thermodynamically favorable.
83. This is due to the anthracene unit, since gold nanoparticles do not emit in this wavelength range.
84. The mixed solution of dyad 1 and gold nanoparticles was left at room temperature for 6 h before the measurement.
85. a) H. Bouas-Laurent, A. Castellan, J. P. Desvergne, R. Lapouyade, Chem. Soc. Rev. 2000, 29, 43-55;
86. b) E. J. Bowen, Advances in Photochemistry Vol. 1, (Eds.: W. A. Noyes, G. S. Hammond, J. N. Pitts), Interscience, NY, 1963, pp. 23-42;
87. c) H. Bouas-Laurent, A. Castellan, J. P. Desvergne, Pure Appl. Chem. 1980, 52, 2633-2648;
88. d) H. Bouas-Laurent, A. Castellan, J. P. Desvergne, R. Lapouyade, Chem. Soc. Rev. 2001, 30, 248-263.
89. After assembly of dyad 1 on the surface of gold nanoparticles, the anthracene units of neighboring molecules of are orientated closely to each other. As a result, it would be more favorable for photodimerization of the anthracene units of the molecules of dyad 1 adsorbed on the surface of the same gold nanoparticle. However, we cannot rule out the possibility that the photodimerization also occurs between molecules of dyad 1 adsorbed on the surfaces of different gold nanoparticles.
90. a) S.-J. Chen, H.-T. Chang, Anal. Chem. 2004, 76, 3727-3734;
91. b) D. J. Maxwell, J. R. Taylor, S. Nie, J. Am. Chem. Soc. 2002, 124, 9606-9612;
92. c) E. Oh, M.-Y. Hong, D. Lee, S.-H. Nam, H. C. Yoon, H.-S. Kim, J. Am. Chem. Soc. 2005, 127, 3270-3271;
93. d) J. M. Kurner, O. S. Wolfbeis, I. Klimant, Anal. Chem. 2002, 74, 2151-2156.
94. M. Brust, M. Walker, D. Betheli, D. J. Schiffrin, R. Whyman, J. Chem. Soc. Chem. Commun. 1994, 801-802.