Optimization of the molecular orbital energies of conjugated polymers for optical amplification of fluorescent sensors

Journal of the American Chemical Society

Volumn 128, Issue 4, 2006, Pages 1188-1196

  Liu, Bin ^a   Bazan, Guillermo C ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHARGE TRANSFER; COMPLEXATION; FLUORESCENCE; QUENCHING; RESONANCE; SYNTHESIS (CHEMICAL);

PHOTOINDUCED CHARGE TRANSFER (PCT); POLYMER FLUORESCENCE; SIGNAL AMPLIFICATION;

ORGANIC POLYMERS;

CATION; DYE; FLUORENE DERIVATIVE; FLUORESCEIN; POLYMER; QUININE SULFATE; SINGLE STRANDED DNA;

ABSORPTION SPECTROSCOPY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIC POTENTIOMETRY; FLUORESCENCE RESONANCE ENERGY TRANSFER; FLUORESCENCE SPECTROSCOPY; MOLECULAR INTERACTION; OPTICS; PHOTOLUMINESCENCE; PROTON NUCLEAR MAGNETIC RESONANCE; SENSOR; SYNTHESIS;

BIOSENSING TECHNIQUES; DNA, SINGLE-STRANDED; FLUORENES; FLUORESCEIN; FLUORESCENCE RESONANCE ENERGY TRANSFER; FLUORESCENT DYES; LUMINESCENT MEASUREMENTS; POLYMERS; THERMODYNAMICS; XANTHENES;

EID: 31944432799     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja055382t     Document Type: Article

References (91)

1. (a) Yang, J. S.; Swager, T. M. J. Am. Chem. Soc. 1998, 120, 11864.
2. (b) Yang, J. S.; Swager, T. M. J. Am. Chem. Soc. 1998, 120, 5321.
3. (c) Leclerc, M. Adv. Mater. 1999, 11, 1491.
4. (d) McQuade, D. T.; Pullen, A. E.; Swager, T. M. Chem. Rev. 2000, 100, 2537.
5. (e) Ewbank, P. C.; Nuding, G.; Suenaga, H.; McCullough, R. D.; Shinkai, S. Tetrahedron Lett. 2001, 42, 155.
6. (f) Ho, H. A.; Boissinot, M.; Bergeron, M. G.; Corbeil, G.; Doré, K.; Boudreau, D.; Leclerc, M. Angew. Chem. 2002, 41, 1548.
7. (g) Kim, I. B.; Erdogan, B.; Wilson, J. N.; Bunz, U. H. F. Eur. J. Chem. 2004, 10, 6247.
8. (h) Rose, A.; Zhu, Z. G.; Madigan, C. F.; Swager, T. M.; Bulovic, V. Nature 2005, 434, 876.
9. (i) Kim, I. B.; Dunkhorst, A.; Gilbert, J.; Bunz, U. H. F. Macromolecules, 2005, 38, 4560.
10. (j) Kim, I. B.; Wilson, J. N.; Bunz, U. H. F. Chem. Commun. 2005, 10, 1273.
11. (a) Chen, L.; McBranch, D. W.; Wang, H.; Helgeson, R.; Wudl, F.; Whitten, D. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 12287.
12. (b) DiCesare, N.; Pinto, M. R.; Schanze, K. S.; Lakowicz, J. R. Langmuir 2002, 18, 7785.
13. (c) Liu, B.; Bazan, G. C. Chem. Mater. 2004, 16, 4467.
14. (d) Leclerc, M.; Ho, H. A. Synlett 2004, 2, 380.
15. (e) Disney, M. D.; Zheng, J.; Swager, T. M.; Seeberger, P. H. J. Am. Chem. Soc. 2004, 126, 13343.
16. (f) Kumaraswamy, S.; Bergstedt, T.; Shi, X.; Rininsland, F.; Kushon, S.; Xia, W. S.; Ley, K.; Achyuthan, K.; McBranch, D.; Whitten, D. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 7511.
17. (g) Pinto, M. R.; Schanze, K. S. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 7505.
18. (h) Le Floch, F.; Ho, H. A.; Harding, L. P.; Bedard, M.; Neagu, P. R.; Leclerc, M. Adv. Mater. 2005, 17, 1251.
19. (i) Ho, H. A.; Bers-Aberem, M.; Leclerc, M. Eur. J. Chem. 2005. 11, 1718.
20. (j) Wosnick, J. H.; Mello, C. M.; Swager, T. M. J. Am. Chem. Soc. 2005, 127, 3400.
21. (k) Nilsson, K. P. R.; Inganäs, O. Nat. Mater. 2003, 2, 419.
22. (l) Nilsson, K. P. R.; Olsson, J. D. M.; Stabo-Eeg, F.; Lindgren, M.; Konradsson, P.; Inganäs, O. Macromolecules 2005, 38, 6813.
23. (m) Herland, A.; Nilsson, K. P. R.; Olsson, J. D. M.; Hammarstrom, P.; Konradsson, P.; Inganas, O. J. Am. Chem. Soc. 2005, 127, 2317.
24. (a) Guillet, J. E. Polymer Photophysics and Photochemistry; Cambridge University Press: Cambridge, 1985.
25. (b) Weber, S. E. Chem. Rev. 1990, 90, 1469.
26. (c) Kauffmann, H. F. Photochemistry and Photophvsics; Radek, J. E.. Ed.; CRC; Boca Raton, FL, 1990; Vol 2.
27. (d) Scholes, G. D.; Ghiggino, K. P. J. Chem. Phys. 1994, 101, 1251.
28. (e) Tasch, S.; List, E. J. W.; Hochfilzer, C.; Leising, G.; Schlichting, P.; Rohr, U.; Geerts, Y.; Scherf, U.; Mullen, K. Phys. Rev. B 1997, 56, 4479.
29. (f) Nguyen, T. Q.; Wu, J. J.; Doan, V.; Schwartz, B. J.; Tolbert, S. H. Science 2000, 288, 652.
30. (g) Pschirer, N. G.; Byrd, K.; Bunz, U. H. F. Macromolecules 2001, 34, 8590.
31. (h) Beljonne, D.; Pourtois, G.; Silva, C.; Hennebicq, E.; Herz, L. M.; Friend, R. H.; Scholes, G. D.; Setayesh, S.; Müllen, K.; Bredas, J. L. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 10982.
32. (i) Liu, B.; Wang, S.; Bazan, G. C.; Mikhailovsky, A. J. Am. Chem. Soc. 2003, 125, 13306.
33. (j) Liu, B.; Bazan, G. C. J. Am. Chem. Soc. 2004, 126, 1942.
34. (k) Hennebicq, E.; Pourtois, G.; Scholes, G.; Herz, L.; Russell, D.; Silva, C.; Setayesh, S.; Grimsdale, A. C.; Müllen, K.; Brédas, J.; Beljonne, D. J. Am. Chem. Soc. 2005, 127, 4744.
35. Lee, D. W.; Swager, T. M. Synlett 2004, 149.
36. (a) Korri, Y. H.; Garnier, F.; Srivastava, P.; Godillot, P.; Yassar, A. J. Am. Chem. Soc. 1997, 119, 7388.
37. (b) Bäuerle, P.; Emge, A. Adv. Mater. 1998, 10, 324.
38. (c) Garnier, F.; Korri, Y. H.; Srivastava, P.; Mandrand, B.; Delair, T. Synth. Met. 1999, 100, 89.
39. (d) Korri-Y, H.; Yassar, A. Biomacromolecules 2001, 2, 58.
40. Swager, T. M. Acc. Chem. Res. 1998, 31, 201.
41. (a) Pinto, M. R.; Schanze, K. S. Synthesis 2002, 9, 1293.
42. (b) Traser, S.; Wittmeyer, P.; Rehahn, M. e-Polymers 2002, No. 032.
43. (a) McQuade, D. T.; Hegedus, A. H.; Swager, T. M. J. Am. Chem. Soc. 2000, 122, 12389.
44. (b) Gaylord, B. S.; Heeger, A. J.; Bazan, G. C. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 10954.
45. (c) Kim, T. H.; Swager, T. M. Angew. Chem. 2003, 42, 4803.
46. (d) Gaylord, B. S.; Heeger, A. J.; Bazan, G. C. J. Am. Chem. Soc. 2003, 125, 896.
47. Dwight, S. J.; Gaylord, B. S.; Hong, J. W.; Bazan, G. C. J. Am. Chem. Soc. 2004, 126, 16850.
48. Förster, T. Ann. Phys. 1948, 2, 55.
49. Lakowicz, J. R. Principles of Fluorescence Spectroscopy; Kluwer Academic/Plenum Publisher: New York, 1999.
50. (a) Halls, J. J. M.; Cornil, J.; Santos, D. A.; Silbey, R.; Hwang, D. H.; Holmes, A. B.; Brédas, J. L.; Friend, R. H. Phys. Rev. B 1999, 60, 5721.
51. (b) Segura, J. L.; Gómez, R.; Martín, N.; Luo, C.; Swartz, A.; Guldi, D. M. Chem. Commun. 2001, 8, 707.
52. (c) Guldi, D. M.; Swartz, A.; Luo, C.; Gómez, R.; Segura, J.; Martín, N. J. Am. Chem. Soc. 2002, 124, 10875.
53. Cornil, J.; Lemaur, V.; Steel, M. C.; Dupin, H.; Burquel, A.; Beljonne, D.; Bredas, J. L. In Organic Photovoltaics; Sun, S. J., Sariciftci, N. S., Eds.; Taylor and Francis: Boca Raton, FL, 2005; p 161.
54. (a) Sariciftci, N. S.; Smilowitz, L.; Heeger, A. J.; Wudl, F. Science 1992, 258, 1474.
55. (b) Marcus, R. A. Angew. Chem. Int. Eng. 1993, 32, 1111.
56. (c) Xu, Q. H.; Moses, D.; Heeger, A. J. Phys. Rev. B 2003, 67, 245417.
57. (d) Brédas, J. L.; Beljonne, D.; Coropceanu, V.; Cornil, J. Chem. Rev. 2004, 104, 4971.
58. (e) Thomas, K. R. J.; Thompson, A. L.; Sivakumar, A. V.; Bardeen, A. J.; Thayumanavan, S. J. Am. Chem. Soc. 2005, 127, 373.
59. Morteani, A. C.; Sreearunothai, P.; Herz, L. M.; Friend, R. H.; Silva, C. Phys. Rev. Lett. 2004, 92, 247402.
60. (a) Ganachaud, F.; Elaissari, A.; Pichot, C.; Laayoun, A.; Cros, P. Langmuir 1997, 13, 701.
61. (b) Liu, B.; Gaylord, B. S.; Wang, S.; Bazan, G. C. J. Am. Chem. Soc. 2003, 125, 6705.
62. (a) Wang, S.; Gaylord, B. S.; Bazan, G. C. Adv. Mater. 2004, 16, 2127.
63. (b) Gaylord, B. S.; Massie, M. R.; Feinstein, S. C. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 34.
64. (c) Xu, H.; Wu, H. P.; Huang, F.; Song, S. P.; Li, W. X.; Cao, Y.; Fan C. H. Nucleic Acids Res. 2005, 33, e83.
65. (a) Wang, S.; Bazan, G. C. Chem. Commun. 2004, 2l, 2508.
66. (b) Wang, S.; Gaylord, B. S.; Bazan, G. C. J. Am. Chem. Soc. 2004, 126, 5446.
67. (c) Tan, C. Y.; Pinto, M. R.; Kose, M. E.; Ghiviga, I.; Schanze, K. S. Adv. Mater. 2004, 16, 1208.
68. (a) Stork, M.; Gaylord, B. S.; Heeger, A. J.; Bazan, G. C. Adv. Mater. 2002, 14, 361.
69. (b) Wang, S.; Liu, B.; Gaylord, B. S.; Bazan, G. C. Adv. Funct. Mater. 2003, 13, 463.
70. (a) Suzuki, A. J. Organomet. Chem. 1999, 576, 147.
71. (b) Liu, B.; Bazan, G. C. In Organic Electroluminescence; Kafafi, Z. H., Ed.; Taylor and Francis: Boca Raton, FL, 2005; p 179.
72. (c) Liu, B.; Yu, W. L.; Lai, Y. H.; Huang, W. Chem. Commun. 2000, 7, 551.
73. (d) Liu, B.; Yu, W. L.; Lai, Y. H.; Huang, W. Chem. Mater. 2001, 13, 1984.
74. (e) Liu, B.; Yu, W. L.; Lai, Y. H.; Huang, W. Macromolecules 2002, 35, 4975.
75. Beragren, M.; Inganäs, O.; Gustalsson, G.; Rasmusson, J.; Anderson, M. R.; Hjertberg, T.; Wennerström, O. Nature 1994, 372, 444.
76. Demas, J. N.; Crosby, G. A. J. Phys. Chem. 1971, 75, 991.
77. Corner, R.; Tryson, G. J. Chem. Phys. 1977, 66, 4413.
78. Mallavia, R.; Montilla, F.; Pastor, I.; Velasquez, P.; Arredondo, V.; Alvarez, A. L.; Mateo, C. R. Macromolecules 2005, 38, 3185.
79. Bard, A. J.; Faulkner, L. R. Electrochemical Methods: John Wiley & Sons: New York, 1980.
80. Torimura, M.; Kurata, S.; Yamada, K.; Yokomaku, T.; Kamagata, Y.; Kanagawa, T.; Kurane, R. Anal. Sci. 2001, 17, 155.
81. (a) Rompaey, E. V.; Sanders, N.; Smedt, S. C.; Demeester, J.; Craenenbroeck, E. V.; Engelborghs, Y. Macromolecules 2000, 33, 8280.
82. (b) Rompaey, E. V.; Engelborghs, Y.; Sanders, N.; Smedt, S. C.; Demeester, J. Pharm. Res. 2001, 18, 928.
83. (c) Lucas, B.; Rompaey, E. V.; Smedt, S. C.; Demeester, J.; Oostveldt, P. V. Macromolecules 2002, 35, 8152.
84. (d) Lucas, B.; Remaut, K.; Braeckmans, K.; Haustraete, J.; Smedt, S. C.; Demeester, J. Macromolecules 2004, 37, 3832.
85. Huang, F.; Wu, H.; Wang, D.; Yang, W.; Cao, Y. Chem. Mater. 2004, 16, 708.
86. Seidel, C. A.; Schulz, M.; Sauer, H. J. Phys. Chem. 1996, 100, 5541.
87. (a) Gebhardt, V.; Bacher, A.; Thelakkat, M.; Stalmach, U.; Meier, H. Schmidt, H. W.; Haarer, D. Adv. Mater. 1999, 11, 119.
88. (b) Chang, R. Hsu, J. H.; Fann, W. S.; Liang, K. K.; Chang, C. H.; Hayashi, M.; Yu, J. Lin, S. H.; Chang, E. C.; Chuang, K. R.; Chen, S. A. Chem. Phys. Lett. 2000, 317, 142.
89. We reemphasize here that the framework we provide for understanding the level of quenching of the dye by the different CCP structures is based on the thermodynamic driving force for PCT. Possible kinetic differences based on the acceleration of charge transfer with increasing driving force within the normal region, as described by Marcus, are not included and may bear an important contribution to the different levels of quenching. See: (a) Creutz, C.; Keller, A. D.; Sutin, N.; Zipp, A. P. J. Am. Chem. Soc. 1982, 104, 3618.
90. (b) Dossot, M.; Allonas, X.; Jacques, P. Phys. Chem. Chem. Phys. 2002, 4, 2989.
91. (c) Sim, E. J. Phys. Chem. B 2005, 109, 11829 and ref 14b.