Mono- and di(dimethylamino)styryl-substituted borondipyrromethene and borondiindomethene dyes with intense near-infrared fluorescence

Chemistry - An Asian Journal

Volumn 1, Issue 1-2, 2006, Pages 176-187

  Yu, Yan Hong ^a   Descalzo, Ana B ^b   Shen, Zhen ^a   Röhr, Holger ^b   Liu, Quan ^a   Wang, Yan Wei ^a   Spieles, Monika ^b   Li, Yi Zhi ^a   Rurack, Knut ^b   You, Xiao Zeng ^a  

^a NANJING UNIVERSITY   (China)

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

Author keywords

Borondipyrromethene; Dyes; Fluorescence; Indicators; Protonation

Indexed keywords

EID: 33748715174     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.200600042     Document Type: Article

References (82)

1. J. Fabian, H. Nakazumi, M. Matsuoka, Chem. Rev. 1992, 92, 1197-1226.
2. S. Därme, J. Imaging Sci. Technol. 1994, 38, 101-117.
3. M. Matsuoka, Mol. Cryst. Liq. Cryst. Sci. Technol. Sect. A 1993, 224, 85-94.
4. J. Fabian, J. Prakt. Chem. 1991, 333, 197-222.
5. S. McWhorter, S. A. Soper, Electrophoresis 2000, 21, 1267-1280.
6. A. R. Swamy, M. I. Danesvar, L. Evans, L. Strekowski, N. Narayanan, F. Szurdoki, I. Wengatz, B. D. Hammock, G. Patonay, ACS Symp. Ser. 1997, 657, 146-161.
7. M. Gurfinkel, S. Ke, X. X. Wen, C. Li, E. M. Sevick-Muraca, Dis. Markers 2003, 19, 107-121.
8. E. Dekker, P. Fockens, Eur. J. Gastroenterol. Hepatol. 2005, 17, 803-808.
9. B. Ballou, L. A. Ernst, A. S. Waggoner, Curr. Med. Chem. 2005, 12, 795-805.
10. K. Licha, C. Olbrich, Adv. Drug Delivery Rev. 2005, 57, 1087-1108.
11. Y. B. Wang, J. H. Yang, X. Wu, L. Li, S. Sun, B. Y. Su, Z. S. Zhao, Anal. Lett. 2003, 36, 2063-2094.
12. N. Tyutyulkov, J. Fabian, A. Mehlhorn, F. Dietz, A. Tadjer, Polymethine Dyes, St. Kliment Ohridski University Press, Sofia, 1991.
13. D. F. O'Brien, T. M. Kelly, L. F. Costa, Photogr. Sci. Eng. 1974, 18, 76-84.
14. R. E. Pagano, O. C. Martin, H. C. Kang, R. P. Haugland, J. Cell Biol. 1991, 113, 1267-1279;
15. J. Karolin, L. B.-Å. Johansson, L. Strandberg, T. Ny, J. Am. Chem. Soc. 1994, 776, 7801-7806;
16. T. G. Pavlopoulos, Prog. Quantum Electron. 2002, 26, 193-224.
17. BDP labels are commercially available under their trademark name, bodipy, from Molecular Probes, http://probes.invitrogen.com/.
18. T. Gareis, C. Huber, O. S. Wolfbeis, J. Daub, Chem. Commun. 1997, 1717-1718;
19. F. Bergström, I. Mikhalyov, P. Hägglöf, R. Wortmann, T. Ny, L. B.-Å. Johansson, J. Am. Chem, Soc. 2002, 124, 196-204;
20. C. Goze, G. Ulrich, L. Charbonnière, M. Cesario, T. Prangé, R. Ziessel, Chem. Eur. J. 2003, 9, 3748-3755;
21. Y. Gabe, Y. Urano, K. Kikuchi, H. Kojima, T. Nagano, J. Am. Chem. Soc. 2004, 126, 3357-3367;
22. G. C. Ping, B. M. Zhu, M. Jabasini, F. Xu, H. Oka, H. Sugihara, Y. Baba, Anal. Chem. 2005, 77, 7282-7287.
23. K. Rurack, M. Kollmannsberger, U. Resch-Genger, J. Daub, J. Am. Chem. Soc. 2000, 122, 968-969.
24. 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;
25. H. Imahori, H. Norieda, H. Yamada, Y. Nishimura, I. Yamazaki, Y. Sakata, S. Fukuzumi, J. Am. Chem. Soc. 2001, 123, 100-110;
26. R. Y. Lai, A. J. Bard, J. Phys. Chem. B 2003, 107, 5036-5042;
27. F. D'Souza, P. M. Smith, M. E. Zandler, A. L. McCarty, M. Itou, Y. Araki, O. Ito, J. Am. Chem. Soc. 2004, 126, 7898-7907;
28. C. Trieflinger, H. Röhr, K. Rurack, J. Daub, Angew. Chem. 2005, 777, 7104-7107;
29. Angew. Chem. Int. Ed. 2005, 44, 6943-6947;
30. H. Röhr, C. Trieflinger, K. Rurack, J. Daub, Chem. Eur. J. 2006, 12, 689-700.
31. M. Kollmannsberger, T. Gareis, S. Heinl, J. Breu, J. Daub, Angew. Chem. 1997, 109, 1391-1393;
32. Angew. Chem. Int. Ed. Engl. 1997, 36, 1333-1335;
33. H. Kim, A. Burghart, M.B. Welch, J. Reibenspies, K. Burgess, Chem. Commun. 1999, 1889-1890;
34. J. Chen, J. Reibenspies, A. Derecskei-Kovacs, K. Burgess, Chem. Commun. 1999, 2501-2502;
35. K. Yamada, T. Toyota, K. Takakura, M. Ishimaru, T. Sugawara, New J. Chem. 2001, 25, 667-669;
36. A. Gossauer, F. Nydegger, T. Kiss, R. Sleziak, H. Stoeckli-Evans, J. Am. Chem. Soc. 2004, 126, 1772-1780;
37. W. Zhao, E. M. Carreira, Angew. Chem. 2005, 117, 1705-1707;
38. Angew. Chem. Int. Ed. 2005, 44, 1677-1679.
39. Z. Shen, H. Röhr, K. Rurack, H. Uno, M. Spieles, B. Schulz, G. Reck, N. Ono, Chem. Eur. J. 2004, 10, 4853-4871.
40. K. Rurack, M. Kollmannsberger, J. Daub, Angew. Chem. 2001, 113, 396-399;
41. Angew. Chem. Int. Ed. 2001, 40, 385-387.
42. K. Rurack, M. Kollmannsberger, J. Daub, New J. Chem. 2001, 25, 289-292.
43. S. Y. Moon, N. R. Cha, Y. H. Kim, S.-K. Chang, J. Org. Chem. 2004, 69, 181-183.
44. C. L. Picou, E. D. Stevens, M. Shah, J. H. Boyer, Acta Crystallogr. Sect. C 1990, 46, 1148-1150;
45. N. Kuhn, A. Kuhn, M. Speis, D. Blaser, R. Boese, Chem. Ber. 1990, 123, 1301-1303.
46. M. Kollmannsberger, K. Rurack, U. Resch-Genger, J. Daub, J. Phys. Chem. A 1998, 102, 10211-10220.
47. Y. Fujimoto, N. Katayama, Y. Ozaki, S. Yasui, K. Iriyama, J. Mol. Struct. 1992, 274, 183-195.
48. O = Onsager cavity radius: E. Lippert, Z. Naturforsch. 1955, 10a, 541-545;
49. E. Lippert, Z. Elektrochem. 1957, 61, 962-975;
50. o was estimated from the AM1-optimized ground-state geometry and further assumptions proposed by Lippert.
51. The dipole moments of 1-4 in the ground state were determined as 4.5, 4.3, 2.7, and 3.6 D for the optimized ground-state geometry by semiempirical AMI calculations.
52. K. Rurack, J. L. Bricks, G. Reck, R. Radeglia, U Resch-Genger, J. Phys. Chem. A 2000, 104, 3087-3109.
53. M. Meyer, J. C. Mialocq, Opt. Commun. 1987, 64, 264-268.
54. em = emission intensity).
55. W. Siebrand, J. Chem. Phys. 1967, 46, 440-447.
56. M. Kollmannsberger, K. Rurack, U. Resch-Genger, W. Rettig, J. Daub, Chem. Phys. Lett. 2000, 329, 363-369.
57. This assumption is considered to be valid, because excited-state processes such as photoisomerization or intersystem crossing do not play a prominent role in BDP and BDI photophysics.
58. P(red)= -1620 mV for 2.
59. 2 to MeCN/MeOH is thus not yet understood.
60. 2O to hexane (Table 2) is also not yet understood. Such phenomena have been reported frequently for various BDP derivatives in various alkane solvents, for example: F. López Arbeloa, T. López Arbeloa, I. López Arbeloa, J. Photochem. Photobiol. A 1999, 121, 177-182;
61. J. Banuelos Prieto, F. López Arbeloa, V. Martinez Martinez, T. Arbeloa Lopez, F. Amat-Guerri, M. Liras, I. López Arbeloa, Chem. Phys. Lett. 2004, 385, 29-35;
62. M. Baruah, W. Qin, N. Basaric, W. M. De Borggraeve, N. Boens, J. Org. Chem. 2005, 70, 4152-4157;
63. W. Qin, T. Rohand, M. Baruah, A. Stefan, M. Van der Auweraer, W. Dehaen, N. Boens, Chem. Phys. Lett. 2006, 420, 562-568; the mechanistic interpretations are not consistent, that is, they range from specific solute-solvent effects through molecular rigidity to intersystem crossing.
64. 2+; see also references [20,33].
65. J. L. Bricks, A. Kovalchuk, C. Trieflinger, M. Nofz, M. Büschel, A. I. Tolmachev, J. Daub, K. Rurack, J. Am. Chem. Soc. 2005, 127, 13522-13529.
66. To assess the generality of the effect of protonation, spectrophotometric and steady-state fluorometric pH titrations were also performed for 3. The neat dye displays a broad band with an absorption maximum at 743 nm in water, and the species in which both potential ICT donor sites are protonated (pH≈0) absorbs with a characteristically narrow, cyanine-like band at 645 nm. However, most probably due to the influence of the 8-hydroxyquinoline moiety under strongly acidic conditions, the typical mirror-image-shaped emission with a maximum at 657 nm is only rather weak. (The peculiarities of 8-hydroxyquinoline as a substituent in the meso position are discussed in a separate section below.) Nonetheless, we anticipate that an analogue of 3 with a phenyl group or, for instance, a benzocrown in the meso position should show similar proton-induced "light-up" features as 4 does.
67. K. Rurack, M. Sczepan, M. Spieles, U. Resch-Genger, W. Rettig, Chem. Phys. Lett. 2000, 320, 87-94.
68. s values of both dimethylamino groups are apparently too similar in organic and mixed aqueous solutions to be unequivocally distinguished from one another, and the first protonation of 1 in such solvents or mixtures occurs statistically at both sites.
69. Owing to the precipitation of this species, quantitative analyses of the changes in the aniline absorption band in the 5.5> pH >2.5 range did not yield very reliable results for the more basic pK values.
70. T. Nishioka, T. Arimura, Y. Suga, S. Murata, M. Tachiya, M. Goto, Bull. Chem. Soc. Jpn. 2001, 74, 2435-2436;
71. Y. K. Wu, X. J. Peng, B. C. Guo, J. L. Fan, Z. C. Zhang, J. Y. Wang, A. J. Cui, Y. L. Gao, Org. Biomol. Chem. 2005, 3, 1387-1392;
72. N. Basaric, M. Baruah, W. Qin, B. Metten, M. Smet, W. Dehaen, N. Boens, Org. Biomol. Chem. 2005, 5, 2755-2761.
73. max ≈ 495 nm) is strongly quenched owing to efficient energy transfer to the BDP. As 2 and 3 are also only weakly fluorescent in highly polar (protic) solvents, the yield of BDP emission upon excitation at 370 nm is also considerably low, and such molecules do not qualify as FRET (fluorescence resonant energy transfer) probes.
74. W. Rettig, Top. Curr. Chem. 1994, 169, 253-299.
75. Bruker (2000). Smart, Saint, Sadabs and Shelxtl. Bruker AXS Inc., Madison, Wisconsin, USA, 2000.
76. J. Olmsted III, J. Phys. Chem. 1979, 83, 2581-2584.
77. D. F. Eaton, Pure Appl. Chem. 1988, 60, 1107-1114.
78. J. Hollandt, R. D. Taubert, J. Seidel, U. Resch-Genger, A. Gugg-Helminger, D. Pfeifer, C. Monte, W. Pilz, J. Fluoresc. 2005, 15, 301-313;
79. U. Resch-Genger, D. Pfeifer, C. Monte, W. Pilz, A. Hoffmann, M. Spieles, K. Rurack, J. Hollandt, D. Taubert, B. Schönenberger, P. Nording, J. Fluoresc. 2005, 15, 315-336.
80. D. N. Dempster, T. Morrow, R. Rankin, G. F. Thompson, Chem. Phys. Lett. 1973, 18, 488-492.
81. U. Resch, K. Rurack, Proc. SPIE-Int. Soc. Opt. Eng. 1997, 3105, 96-103.
82. K. Rurack, J. L. Bricks, B. Schulz, M. Maus, G. Reck, U. Resch-Genger, J. Phys. Chem. A 2000, 104, 6171-6188.