Proton-and redox-controlled switching of photo-and electrochemiluminescence in thiophenyl-substituted boron-dipyrromethene dyes

Chemistry - A European Journal

Volumn 12, Issue 3, 2006, Pages 689-700

  Röhr, Holger ^a,c   Trieflinger, Christian ^b   Rurack, Knut ^a   Daub, Jörg ^b  

^a BAM FEDERAL INSTITUTE FOR MATERIALS RESEARCH AND TESTING   (Germany)

^b UNIVERSITY OF REGENSBURG   (Germany)

^c FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

Boron dipyrromethene; Electrochemiluminescence; Fluorescence; Molecular switches; Redox chemistry; Thiol disulfide chemistry

Indexed keywords

MOLECULAR SWITCHES; REDOX CHEMISTRY; REDOX SWITCHES;

CHROMOPHORES; DIMERS; ELECTROLUMINESCENCE; MONOMERS; OXIDATION; PHOTOLUMINESCENCE; PROTONS; REDOX REACTIONS; SWITCHING;

DYES;

BORON DERIVATIVE; DIPYRROMETHENE; DRUG DERIVATIVE; FLUORESCENT DYE; FUSED HETEROCYCLIC RINGS; PHENOL DERIVATIVE; PORPHOBILINOGEN; THIOL DERIVATIVE; THIOPHENOL;

ARTICLE; CHEMISTRY; CHEMOLUMINESCENCE; ELECTROCHEMISTRY;

BORON COMPOUNDS; CHEMILUMINESCENT MEASUREMENTS; ELECTROCHEMISTRY; FLUORESCENT DYES; HETEROCYCLIC COMPOUNDS, 2-RING; PHENOLS; PORPHOBILINOGEN; SULFHYDRYL COMPOUNDS;

EID: 30844438945     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200500729     Document Type: Article

References (122)

1. a) L. Pu, Chem. Rev. 2004, 104, 1687-1716;
2. b) A. P. de Silva, B. McCaughan, B. O. F. McKinney, M. Querol, Dalton Trans. 2003, 1902-1913;
3. c) R. Martinez-Manez, F. Sancenon, Chem. Rev. 2003, 103, 4419-4476.
4. a) F. M. Raymo, M. Tomasulo, Chem. Soc. Rev. 2005, 34, 327-336;
5. b) Molecular Switches (Ed.: B. Feringa), Wiley-VCH, Weinheim, 2002;
6. c) A. P. de Silva, D. B. Fox, T. S. Moody, S. M. Weir, Trends Biotechnol. 2001, 19, 29-34.
7. a) A. P. de Silva, N. D. McClenaghan, Chem. Eur. J. 2003, 10, 574-586;
8. b) V. Balzani, A. Credi, M. Venturi, Chem. Phys. Chem. 2003, 3, 49-59;
9. c) F. M. Raymo, Adv. Mater. 2002, 14, 401-414.
10. a) Special Issue (6) on "Molecular Machines" Acc. Chem. Res. 2001, 34, 409-522;
11. b) C. P. Mandl, B. König, Angew. Chem. 2004, 116, 1650-1652;
12. Angew. Chem. Int. Ed. 2004, 43, 1622-1624;
13. c) Molecular Devices and Machines, A Journey into the Nanoworld (Eds.: V. Balzani, M. Venture, A. Credi), Wiley-VCH, Weinheim, 2003;
14. d) A. R. Pease, J. F. Stoddart, Struct. Bonding 2001, 99, 189-236.
15. a) J. R. Heath, Pure Appl. Chem. 2000, 72, 11-20;
16. b) D. T. McQuade, A. E. Pullen, T. M. Swager, Chem. Rev. 2000, 100, 2537-2574;
17. c) A. Harriman, R. Ziessel, Chem. Commun. 1996, 1707-1716.
18. a) T. G. Goodson, III, Acc. Chem. Res. 2005, 38, 99-107;
19. b) J. M. J. Frechet, J. Polym. Sci. Part A: Polym. Chem. 2003, 41, 3713-3725;
20. c) V. Balzani, P. Ceroni, M. Maestri, C. Saudan, V. Vicinelli, Top. Curr. Chem. 2003, 228, 159-191;
21. d) M. A. Miller, R. K. Lammi, S. Prathapan, D. Holten, J. S. Lindsey, J. Org. Chem. 2000, 65, 6634-6649;
22. e) A. Burghart, L. H. Thoresen, J. Chen, K. Burgess, F. Bergström, L. B.-Å. Johansson, Chem. Commun. 2000, 2203-2204;
23. f) J. Y. Ju, A. N. Glazer, R. A. Mathies, Nucleic Acids Res. 1996, 24, 1144-1148.
24. a) G. M. Tsivgoulis, J.-M. Lehn, Adv. Mater. 1997, 9, 627-630;
25. b) H. Spreitzer, J. Daub, Chem. Eur. J. 1996, 2, 1150-1158;
26. c) J. Daub, C. Fischer, J. Salbeck, K. Ulrich, Adv. Mater. 1990, 2, 366-369.
27. a) K. Rurack, M. Kollmannsberger, J. Daub, Angew. Chem. 2001, 113, 396-399;
28. Angew. Chem. Int. Ed. 2001, 40, 385-387;
29. b) G. Hennrich, H. Sonnenschein, U. Resch-Genger, J. Am. Chem. Soc. 1999, 121, 5073-5074;
30. c) M. Kollmannsberger, T. Gareis, S. Heinl, J. Breu, J. Daub, Angew. Chem. 1997, 109, 1391-1393;
31. Angew. Chem. Int. Ed. Engl. 1997, 36, 1333-1335.
32. a) L. Gobbi, P. Seiler, F. Diederich, V. Gramlich, C. Boudon, J.-P. Gisselbrecht, M. Gross, Helv. Chim. Acta 2001, 84, 743-777;
33. b) L. Gobbi, P. Seiler, F. Diederich, Angew. Chem. 1999, 111, 737-740;
34. Angew. Chem. Int. Ed. Engl. 1999, 38, 674-678.
35. a) C. Trieflinger, K. Rurack, J. Daub, Angew. Chem. 2005, 117, 2328-2331;
36. Angew. Chem. Int. Ed. 2005, 44, 2288-2291;
37. b) J. Achatz, C. Fischer, J. Salbeck, J. Daub, J. Chem. Soc. Chem. Commun. 1991, 504-507.
38. A number of redox-active thiol/disulfide switches that can be probed by various other instrumental methods have been reported; see, for example: a) H. Graubaum, F. Tittelbach, G. Lutze, K. Gloe, M. Mackrodt, J. Prakt. Chem. 1997, 359, 55-58;
39. b) M. Irie, O. Miyatake, K. Uchida, T. Eriguchi, J. Am. Chem. Soc. 1994, 116, 9894-9900;
40. c) S. Shinkai, K. Inuzuka, O. Miyazaki, O. Manabe, J. Org. Chem. 1984, 49, 3440-3442;
41. d) S. Shinkai, K. Inuzuka, O. Manabe, Chem. Lett. 1983, 747-750;
42. e) T. Minami, S. Shinkai, O. Manabe, Tetrahedron Lett. 1982, 23, 5167-5170. An example of a thiol/disulfide-controlled molecular machine based on rotaxanes has also been published recently
43. f) Y. Furusho, T. Hasegawa, A. Tsuboi, N. Kihara, T. Takata, Chem. Lett. 2000, 18-19.
44. a) A. P. Fernandes, A. Holmgren, Antioxid. Redox Signal. 2004, 6, 63-74;
45. b) D. Barford, Curr. Opin. Struct. Biol. 2004, 14, 679-686;
46. c) K. Linke, U. Jakob, Antioxid. Redox Signal. 2003, 5, 425-434;
47. d) H. Sies, Free Radic. Biol. Med. 1999, 27, 916-921.
48. a) G. T. Hanson, R. Aggeler, D. Oglesbee, M. Cannon, R. A. Capaldi, R. Y. Tsien, S. J. Remington, J. Biol. Chem. 2004, 279, 13044-13053;
49. b) H. Østergaard, A. Henriksen, F. G. Hansen, J. R. Winther, EMBO J. 2001, 20, 5853-5862.
50. H. Østergaard, C. Tachibana, J. R. Winther, J. Cell Biol. 2004, 166, 337-345.
51. a) T. Sakata, Y. Yan, G. Marriott, J. Org. Chem. 2005, 70, 2009-2013;
52. b) P. Ge, P. R. Selvin, Bioconjugate Chem. 2003, 14, 870-876.
53. R. Rinaldi, G. Maruccio, A. Biasco, P. Visconti, V. Arima, R. Cingolani, Ann. N.Y. Acad. Sci. 2003, 1006, 187-197.
54. a) P. Toele, H. Zhang, C. Trieflinger, J. Daub, M. Glasbeek, Chem. Phys. Lett. 2003, 368, 66-75;
55. b) M. Kollmannsberger, K. Rurack, U. Resch-Genger, J. Daub, J. Phys. Chem. A 1998, 102, 10211-10220;
56. c) J. Karolin, L. B.-A. Johansson, L. Strandberg, T. Ny, J. Am. Chem. Soc. 1994, 116, 7801-7806;
57. d) J. A. Pardoen, J. Lugtenburg, G. W. Canters, J. Phys. Chem. 1985, 89, 4272-4277.
58. a) W. Zhao, E. M. Carreira, Angew. Chem. 2005, 117, 1705-1707;
59. Angew. Chem. Int. Ed. 2005, 44, 1677-1679;
60. b) Z. Shen, H. Röhr, K. Rurack, H. Uno, M. Spieles, B. Schulz, G. Reck, N. Ono, Chem. Eur. J. 2004, 10, 4853-4871;
61. c) K. Rurack, M. Kollmannsberger, J. Daub, New J. Chem. 2001, 25, 289-292;
62. d) H. Kim, A. Burghart, M. B. Welch, J. Reibenspies, K. Burgess, Chem. Commun. 1999, 1889-1890;
63. e) J. Chen, J. Reibenspies, A. Derecskei-Kovacs, K. Burgess, Chem. Commun. 1999, 2501-2502.
64. a) Y. Gabe, Y. Urano, K. Kikuchi, H. Kojima, T. Nagano, J. Am. Chem. Soc. 2004, 126, 3357-3367;
65. b) C. Goze, G. Ulrich, L. Charbonnière, M. Cesario, T. Prangé, R. Ziessel, Chem. Eur. J. 2003, 9, 3748-3755;
66. c) R. W. Wagner, J. S. Lindsey, Pure Appl. Chem. 1996, 68, 1373-1380.
67. a) G. Beer, K. Rurack, J. Daub, Chem. Commun. 2001, 1138-1139;
68. b) G. Beer, C. Niederalt, S. Grimme, J. Daub, Angew. Chem. 2000, 112, 3385-3388;
69. Angew. Chem. Int. Ed. 2000, 39, 3252-3255;
70. c) M. Kollmannsberger, K. Rurack, U. Resch-Genger, W. Rettig, J. Daub, Chem. Phys. Lett. 2000, 329, 363-369.
71. a) J. M. Brom, Jr., J. L. Langer, J. Alloys Compd. 2002, 338, 112-115;
72. b) R. Y. Lai, A. J. Bard, J. Phys. Chem. B 2003, 106, 5036-5042.
73. a) L. Milanesi, G. D. Reid, G. S. Beddard, C. A. Hunter, J. P. Waltho, Chem. Eur. J. 2004, 10, 1705-1710;
74. b) W. M. Macindoe, A. H. van Oijen, G.-J. Boons, Chem. Commun. 1998, 847-848.
75. F. Bergström, I. Mikhalyov, P. Hägglöf, R. Wortmann, T. Ny, L. B.-Å. Johansson, J. Am. Chem. Soc. 2002, 124, 196-204.
76. 2 failed, and cyclovoltammetric measurements suggested that the close vicinity of nucleophilic thiol group and BDP residue most probably renders the monomer rather unstable.
77. Y. Fujimoto, N. Katayama, Y. Ozaki, S. Yasui, K. Iriyama, J. Mol. Struct. 1992, 274, 183-195.
78. K. Rurack, M. Kollmannsberger, U. Resch-Genger, J. Daub, J. Am. Chem. Soc. 2000, 122, 968-969.
79. T. Gareis, C. Huber, O. S. Wolfbeis, J. Daub, Chem. Commun. 1997, 1717-1718.
80. Because of the sensitivity of such thiolates towards oxidation, these measurements were performed under Ar. Note that the use of such conditions has a negligible influence on the fluorescence features of the title dyes: Φ = 0.64 and 0.65 for pSH-1 in aerated and de-aerated MeCN, for example.
81. W. Rettig, Top. Curr. Chem. 1994, 169, 253-299.
82. AMPAC V6.55, Seitlichem, Inc. M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, J. J. P. Stewart, J. Am. Chem. Soc. 1985, 107, 3902-3909.
83. Such a dependence of the intensity of the bathochromically shifted transition on the interannular twist angle has also been found for the phenolate anion of 9-(p-hydroxyphenyl)acridine, V. Zanker, A. Reichel, Z. Elektrochem. 1959, 63, 1133-1140
84. and V. Zanker, A. Reichel, Z. Elektrochem. 1960, 64, 431-437.
85. a) Y. Wang, C.-P. Chang, H. Tian, Dyes Pigm. 2002, 54, 265-274;
86. b) Y. Wang, C.-P. Chang, Y. Wu, H. Tian, Dyes Pigm. 2001, 57, 127-136.
87. 2 suggest that exciton coupling such as has been observed for λ-conjugated pre-twisted BDPs by Falk and Schoppel (see ref. [39]) does not play a major role in the present case.
88. R. F. Khairutdinov, N. Serpone, J. Phys. Chem. B 1997, 101, 2602-2610.
89. W. R. Ware in Photochemistry in Organized and Constrained Media (Ed.: V. Ramamurthy), VCH, New York, 1991, pp. 563-602.
90. a) K. Rurack, K. Hoffmann, W. Al-Soufi, U. Resch-Genger, J. Phys. Chem. B 2002, 106, 9744-9752;
91. b) R. Fritz, A. Kungl, W. Rettig, J. Springer, Chem. Phys. Lett. 1996, 260, 409-417;
92. c) F. V. Bright, G. C. Catena, J. Huang, J. Am. Chem. Soc. 1990, 112, 1343-1346.
93. D. R. James, Y.-S. Liu, P. De Mayo, W. R. Ware, Chem. Phys. Lett. 1985, 120, 460-465.
94. S. G. Tarasov, J. R. Casas-Finet, W. M. Cholody, C. J. Michejda, Photochem. Photobiol. 1999, 70, 568-578.
95. H. Falk, G. Schoppel, Monatsh. Chem. 1990, 121, 67-76.
96. F. Li, S. I. Yang, Y. Ciringh, J. Seth, I. C. H. Martin, D. L. Singh, D. Kim, R. R. Birge, D. F. Bocian, D. Holten, J. S. Lindsey, J. Am. Chem. Soc. 1998, 120, 10001-10017.
97. 1 state was found to be of negligible importance (e.g. refs. [17a, 18b], J. Banuelos Prieto, F. López Arbeloa, V. Martinez - Martinez, I. López Arbeloa, Chem. Phys. 2004, 296, 13-22)
98. and significantly lower than in rhodamine dyes; see, for example, F. Liang, H. P. Zeng, Z. R. Sun, Y. Z. Yuan, Z. G. Yao, Z. Z. Xu, J. Opt. Soc. Am. B 2001, 18, 1841-1845.
99. +/Fc.
100. 2.
101. S. Antonello, K. Daasbjerg, H. Jensen, F. Taddei, F. Maran, J. Am. Chem. Soc. 2003, 125, 14905-14916.
102. Diaryl disulfides are known to be reductively cleaved to thiolate anions, see refernce [44] and references therein.
103. By use of the Digisim 3.03a program; M. Rudolph, S. W. Feldberg, Digisim 3.03a, Bioanalytical Systems, Inc., West Lafayette, IN, USA, 1994-2000.
104. a) K. Kelnhofer, A. Knorr, Y. H. Tak, H. Bässler, J. Daub, Acta Polym. 1997, 48, 188-192;
105. b) J. Daub, K. Kelnhofer, T. Gareis, A. Knorr, M. Kollmannsberger, Y.-H. Tak, H. Bässler, Polym. Preprints 1997, 38, 339-340;
106. c) J. Strauss, J. Daub, Adv. Mater. 2002, 14, 1652-1655;
107. d) J. Strauss, J. Daub, Adv. Mater. 2003, 15, 258;
108. e) C. Trieflinger, H. Röhr, K. Rurack, J. Daub, Angew. Chem. 2005, 117, DOI: 10.1002/ange. 200501573;
109. Angew. Chem. Int. Ed. 2005, 44, DOI: 10.1002/anie.200501573.
110. M. M. Richter, Chem. Rev. 2004, 104, 3003-3036.
111. The bathochromic shift of ca. 20 nm between the fluorescence and the ECL spectrum is well known and can be attributed to reabsorption effects due to the higher dye concentration used in the ECL experiment and to the different dielectric properties of the supporting electrolyte.
112. [50) a) G.-Kempter, W. Pötter, N. Binding, H. Kläning, U. Witting, U. Karst, Anal Chim. Acta 2000, 410, 47-64;
113. b) D. Blakeslee, M. G. Baines, J. Immunol. Methods 1976, 13, 305-320;
114. c) Reactive Dyes in Protein and Enzyme Technology (Eds. Y. D. Clonis, A. Atkinson, C. J. Bruton, C. R. Lowe), Macmillan, Basingstoke, UK, 1987.
115. a) J. Salbeck, Dissertation, Universität Regensburg, 1988;
116. b) J. Salbeck, J. Electroanal. Chem. 1993, 340, 169-175.
117. Synthesized according to P. R. Menard, J. T. Suh, H. Jones, B. Love, E. S. Neiss, J. Wilde, A. Schwab, W. S. Mann, J. Med. Chem. 1985, 28, 328-332.
118. J. Olmsted, III, J. Phys. Chem. 1979, 83, 2581-2584.
119. U. Resch, K. Rurack, Proc. SPIE-Int. Soc. Opt. Eng. 1997, 3105, 96-103.
120. J. Salbeck, Anal. Chem. 1993, 65, 2169-2173,
121. M. Bueschel, C. Stadler, C. Lambert, M. Beck, J. Daub, J. Electroanal. Chem. 2000, 484, 24-32.
122. S. Hien, Ph.D. Thesis, University of Regensburg, 1995.