Fast and stable photochromic oxazines for fluorescence switching

Langmuir

Volumn 27, Issue 19, 2011, Pages 11773-11783

  Deniz, Erhan ^a   Tomasulo, Massimiliano ^a   Cusido, Janet ^a   Sortino, Salvatore ^a,b   Raymo, Françsco M ^a  

^a Department of Biology   (United States)

^b UNIVERSITY OF CATANIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL SAMPLES; EMISSION INTENSITY; FLUORESCENCE MICROSCOPES; FLUORESCENCE SWITCHING; INTERCONVERSIONS; MOLECULAR PROBES; NANOMETER LEVEL; OPTICAL CONTROL; OPTICAL STIMULATION; PHOTO-INDUCED; PHOTOCHROMIC COMPOUND; PHOTOCHROMIC OXAZINES; PHOTOCHROMIC SWITCHES; PHOTOPHYSICAL PROPERTIES; REVERSIBLE TRANSFORMATION; SPATIAL RESOLUTION; SUPER RESOLUTION IMAGING; SWITCHABLE; SWITCHING CYCLES; SWITCHING SPEED; TIME-SCALES;

FATIGUE OF MATERIALS; FLUORESCENCE; ISOMERS; NITROGEN COMPOUNDS; PHOTOCHROMISM; VISUALIZATION;

FLUOROPHORES;

OXAZINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; FLUORESCENCE; PHOTOCHEMISTRY; ULTRAVIOLET RADIATION;

FLUORESCENCE; MOLECULAR STRUCTURE; OXAZINES; PHOTOCHEMICAL PROCESSES; ULTRAVIOLET RAYS;

EID: 80053312300     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la201062h     Document Type: Article

References (99)

1. Lakowicz, J. R. Principles of Fluorescence Spectroscopy; Springer: New York, 2006.
2. Murphy, D. B. Fundamentals of Light Microscopy and Electronic Imaging; Wiley-Liss: New York, 2001.
3. Pawley, J. B., Ed.; Handbook of Biological Confocal Microscopy; Springer: New York, 2006.
4. Born, M.; Wolf, E. Principles of Optics; Cambridge University Press: Cambridge, U.K., 2002.
5. Fernández-Suárez, M.; Ting, A. Y. Nat. Rev. Mol. Cell. Biol. 2008, 9, 929-943
6. Huang, B.; Bates, M.; Zhuang, X. Annu. Rev. Biochem. 2009, 78, 993-1016
7. Hell, S. W. Nat. Methods 2009, 6, 24-32
8. Heilemann, M.; Dedecker, P.; Hofkens, J.; Sauer, M. Laser Photon Rev. 2009, 3, 180-202
9. Toomre, D.; Bewersdorf, J. Annu. Rev. Cell Dev. Biol. 2010, 26, 285-314
10. Vogelsang, J.; Steinhauer, C.; Forthmann, C.; Stein, I. H.; Person-Skergo, B.; Cordes, T.; Tinnefeld, P. ChemPhysChem 2010, 11, 2475-2490
11. Thompson, M. A.; Biteen, J. S.; Lord, S. J.; Conley, N.; Moerner, W. E. Methods Enzymol. 2010, 475, 27-59
12. Cusido, J.; Impellizzeri, S.; Raymo, F. M. Nanoscale 2011, 3, 59-70
13. Dorion, G. H.; Wiebe, A. F. Photochromism; Focal Press: New York, 1970.
14. Brown, G. H., Ed. Photochromism; Wiley: New York, 1971.
15. El'tsov, A. V., Ed. Organic Photochromes; Consultants Bureau: New York, 1990.
16. Bouas-Laurent, H.; Dürr, H., Eds. Photochromism: Molecules and Systems; Elsevier: Amsterdam, 1990.
17. Crano, J. C.; Guglielmetti, R., Eds. Organic Photochromic and Thermochromic Compounds; Plenum Press: New York, 1999.
18. Irie, M. Chem. Rev. 2000, 100, 1683-1890
19. Kuz'min, M. G.; Koz'menko, M. V. In Organic Photochromes; El'tsov, A. V., Ed.; Consultants Bureau: New York, 1990; pp 245-265.
20. Raymo, F. M.; Tomasulo, M. Chem. Soc. Rev. 2005, 34, 327-336
21. Raymo, F. M.; Tomasulo, M. J. Phys. Chem. A 2005, 109, 7343-7352
22. Cusido, J.; Deniz, E.; Raymo, F. M. Eur. J. Org. Chem. 2009, 2031-2045
23. Yildiz, I.; Deniz, E.; Raymo, F. M. Chem. Soc. Rev. 2009, 38, 1859-1867
24. Gross, H.; Dürr, H.; Retting, W. J. Photochem. 1984, 26, 165-178
25. Görner, H.; Fischer, C.; Gierisch, S.; Daub, J. J. Phys. Chem. 1993, 97, 4110-4117
26. Weber, C.; Rustemeyer, F.; Dürr, H. Adv. Mater. 1998, 10, 1348-1351
27. Sheepwash, M.; Mitchell, R. H.; Bohne, C. J. Am. Chem. Soc. 2002, 124, 4693-4700
28. Liang, Y.; Dvornikov, A. S.; Rentzepis, P. M. J. Mater. Chem. 2003, 13, 286-290
29. Myles, A. J.; Branda, N. R. J. Am. Chem. Soc. 2001, 123, 177-178
30. Straight, S. D.; Andréasson, J.; Kodis, G.; Bandyopadhyay, S.; Mitchell, R. H.; Moore, T. A.; Moore, A. L.; Gust, D. J. Am. Chem. Soc. 2005, 127, 9403-9409
31. Liu, L.-H.; Nakatani, K.; Pansu, R.; Vachon, J.-J.; Tauc, P.; Ishow, E. Adv. Mater. 2007, 19, 433-436
32. Berberich, M.; Krause, A.-M.; Orlandi, M.; Scandola, F.; Würthner, F. Angew. Chem., Int. Ed. 2008, 47, 6616-6619
33. Bahr, J. L.; Kodis, G.; de la Garza, L.; Lin, S.; Moore, A. L.; Moore, T. A.; Gust, D. J. Am. Chem. Soc. 2001, 123, 7124-7133
34. Myles, A.; Branda, N. R. Adv. Funct. Mater. 2002, 12, 167-173
35. Giordano, L.; Jovin, T. M.; Irie, M.; Jares-Erijman, E. A. J. Am. Chem. Soc. 2002, 124, 7481-7489
36. Harbron, E. J.; Vicente, D. A.; Hoyt, M. T. J. Phys. Chem. B 2004, 108, 18789-18792
37. Bossi, M.; Belov, V.; Polyakova, S.; Hell, S. W. Angew. Chem., Int. Ed. 2006, 45, 7462-7465
38. Jukes, R. T.; Adamo, V.; Hartl, F.; Belser, P.; De Cola, L. Inorg. Chem. 2004, 43, 2779-2792
39. Bertelson, R. C. In Photochromism; Brown, G. H., Ed.; Wiley: New York, 1971; pp 45-431.
40. Bertelson, R. C. In Organic Photochromic and Thermochromic Compounds; Crano, J. C.; Guglielmetti, R., Eds.; Plenum Press: New York, 1999; Vol. 1, pp 11-83.
41. Kholmanskii, A. S.; Dyumanev, K. M. Russ. Chem. Rev. 1987, 56, 136-151
42. Guglielmetti, R. In Photochromism: Molecules and Systems; Dürr, H.; Bouas-Laurent, H., Eds.; Elsevier: Amsterdam, 1990; pp 314-466 and 855-878.
43. Ichimura, K. In Photochromism: Molecules and Systems; Dürr, H.; Bouas-Laurent, H., Eds.; Elsevier: Amsterdam, 1990; pp 903-918.
44. Ichimura, K.; Seki, T.; Kawamishi, Y.; Suzuki, Y.; Sakuragi, M.; Tamaki, T. In Photo-Refractive Materials for Ultrathin Density Optical Memory; Irie, M., Ed.; Elsevier: Amsterdam, 1994; pp 55-83.
45. Ichimura, K. In Photochromic Polymers; Crano, J. C.; Guglielmetti, R., Eds.; Plenum Press: New York, 1999; Vol. 2, pp 9-63.
46. Ichimura, K. Chem. Rev. 2000, 100, 1847-1873
47. Crano, J. C.; Kwak, W. S.; Welch, C. N. In Applied Photochromic Polymer Systems; McArdle, C. B., Ed.; Blackie: Glasgow, 1992; pp 31-79.
48. Krongauz, V. In Applied Photochromic Polymer Systems; McArdle, C. B., Ed.; Blackie: Glasgow, 1992; pp 121-173.
49. Berkovic, G.; Krongauz, V.; Weiss, V. Chem. Rev. 2000, 100, 1741-1754
50. Irie, M. In Applied Photochromic Polymer Systems; McArdle, C. B., Ed.; Blackie: Glasgow, 1992; pp 174-206.
51. Hibino, J.; Hashida, T.; Suzuki, M. In Photo-Refractive Materials for Ultrathin Density Optical Memory; Irie, M., Ed.; Elsevier: Amsterdam, 1994; pp 25-53.
52. Kawata, S.; Kawata, Y. Chem. Rev. 2000, 100, 1777-1788
53. Delaire, J. A.; Nakatani, K. Chem. Rev. 2000, 100, 1817-1845
54. Tamai, N.; Miyasaka, H. Chem. Rev. 2000, 100, 1875-1890
55. Minkin, V. I. Chem. Rev. 2004, 104, 2751-2776
56. Tomasulo, M.; Deniz, E.; Alvarado, R. J.; Raymo, F. M. J. Phys. Chem. C 2008, 112, 8038-8045
57. Deniz, E.; Tomasulo, M.; DeFazio, R. A.; Watson, B. D.; Raymo, F. M. Phys. Chem. Chem. Phys. 2010, 12, 11630-11634
58. Atabekyan, L. S.; Chibisov, A. K. Zh. Prikl. Spektrosk. 1987, 46, 651-654
59. Görner, H.; Atabekyan, L. S.; Chibisov, A. K. Chem. Phys. Lett. 1996, 260, 59-64
60. Görner, H. Chem. Phys. 1997, 222, 315-329
61. Chibisov, A. K.; Görner, H. J. Photochem. Photobiol., A 1997, 105, 261-267
62. Chibisov, A. K.; Görner, H. J. Phys. Chem. A 1997, 101, 4305-4312
63. Görner, H. Chem. Phys. Lett. 1998, 282, 381-390
64. Görner, H. Phys. Chem. Chem. Phys. 2001, 3, 416-423
65. Krysanov, S. A.; Alfimov, M. V. Chem. Phys. Lett. 1982, 91, 77-80
66. Krysanov, S. A.; Alfimov, M. V. Laser Chem. 1984, 4, 129-138
67. Kalisky, Y.; Orlowski, T. E.; Williams, D. J. J. Phys. Chem. 1983, 87, 5333-5338
68. Ito, T.; Hiramatsu, M.; Hirano, I.; Ohtani, H. Macromolecules 1990, 23, 4528-4532
69. Ito, T.; Hiramatsu, M.; Hosoda, M.; Tsuchiya, Y. Rev. Sci. Instrum. 1991, 62, 1415-1419
70. Ernsting, N. P.; Arthen-Engeland, T. J. Phys. Chem. 1991, 95, 5502-5509
71. Irie, M.; Menju, A.; Hayashi, K. Macromolecules 1979, 12, 1176-1180
72. Krongauz, V.; Kiwi, J.; Grätzel, M. J. Photochem. 1980, 13, 89-97
73. Kalisky, Y.; Williams, D. J. Macromolecules 1984, 17, 292-296
74. Lenoble, C.; Becker, R. S. J. Phys. Chem. 1986, 90, 62-65
75. Tamaki, T.; Sakuragi, M.; Ichimura, K.; Aoki, K. Chem. Phys. Lett. 1989, 161, 23-26
76. Malkin, Ya. N.; Krasieva, T. B.; Kuzmin, V. A. J. Photochem. Photobiol., A 1989, 49, 75-88
77. Sakuragi, M.; Aoki, K.; Tamaki, T.; Ichimura, K. Bull. Chem. Soc. Jpn. 1990, 63, 74-79
78. Salemi, C.; Giusti, G.; Guglielmetti, R. J. Photochem. Photobiol., A 1995, 86, 247-252
79. Sheng, Y.; Leszcynski, J.; Garcia, A. A.; Rosario, R.; Gust, D.; Springer, J. J. Phys. Chem. B 2004, 108, 16233-16243
80. Raymo, F. M.; Giordani, S. J. Am. Chem. Soc. 2001, 123, 4651-4652
81. Raymo, F. M.; Giordani, S.; White, A. J. P.; Williams, D. J. J. Org. Chem. 2003, 68, 4158-4169
82. Tomasulo, M.; Sortino, S.; Raymo, F. M. Org. Lett. 2005, 7, 1109-1112
83. Tomasulo, M.; Sortino, S.; White, A. J. P.; Raymo, F. M. J. Org. Chem. 2005, 70, 8180-8189
84. Tomasulo, M.; Sortino, S.; Raymo, F. M. Asian Chem. Lett. 2007, 11, 219-222
85. 1 of 4-nitroanisole has a subnanosecond lifetime in acetonitrile (Mir, M.; Jansen, L. M. G.; Wilkinson, F.; Bourdelande, J. L.; Marquet, J. J. Photochem. Photobiol., A 1998, 113, 113-117)
86. Tomasulo, M.; Raymo, F. M. Org. Lett. 2005, 7, 4633-4636
87. Tomasulo, M.; Sortino, S.; White, A. J. P.; Raymo, F. M. J. Org. Chem. 2006, 71, 744-753
88. Åxman Petersen, M.; Deniz, E.; Brøndsted Nielsen, M.; Sortino, S.; Raymo, F. M. Eur. J. Org. Chem. 2009, 4333-4339
89. Tomasulo, M.; Sortino, S.; Raymo, F. M. Adv. Mater. 2008, 20, 832-835
90. Tomasulo, M.; Sortino, S.; Raymo, F. M. J. Org. Chem. 2008, 73, 118-126
91. Tomasulo, M.; Sortino, S.; Raymo, F. M. J. Photochem. Photobiol., A 2008, 200, 44-49
92. Deniz, E.; Tomasulo, M.; Sortino, S.; Raymo, F. M. J. Phys. Chem. C 2009, 113, 8491-8497
93. Oxazine 20a switches to corresponding zwitterionic isomer 20b upon ultraviolet illumination. (-61b, 61c) The quantum yield for the photoinduced ring-opening process is 0.03 (φ in Table 1), and the lifetime of the photogenerated isomer is 22 ns (τ in Table 1). The photochemical properties of this compound are also reported in Barkauskas, M.; Martynaitis, V.; Shachkus, A. A.; Rotomskis, R.; Sirutkaitis, V.; Vengris, M. Lith. J. Phys. 2008, 48, 231-242
94. Shachkus, A. A.; Degutis, J.; Jezerskaite, A. In Chemistry of Heterocyclic Compounds; Kovac, J.; Zalupsky, P., Eds.; Elsevier: Amsterdam, 1987; Vol. 35, pp 518-520.
95. Shachkus, A. A.; Degutis, J.; Urbonavichyus, A. G. Khim. Geterotskil. Soed. 1989, 5, 672-676
96. Chem. Heterocycl. Compd. 1989, 562-565.
97. Deniz, E.; Sortino, S.; Raymo, F. M. J. Phys. Chem. Lett. 2010, 1, 1690-1693
98. Deniz, E.; Ray, S.; Tomasulo, M.; Impellizzeri, S.; Sortino, S.; Raymo, F. M. J. Phys. Chem. A 2010, 114, 11567-11575
99. Deniz, E.; Sortino, S.; Raymo, F. M. J. Phys. Chem. Lett. 2010, 1, 3506-3509