Optical writing and reading with bilayer assemblies of photosensitive and fluorescent films

Journal of Materials Chemistry

Volumn 15, Issue 40, 2005, Pages 4354-4360

  Tomasulo, Massimiliano ^a   Raymo, Françisco M ^a  

^a Department of Biology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION CHANGES; BILAYER ASSEMBLIES; OPTICAL WRITING; PHOTOCHEMICAL TRANSFORMATION;

ABSORPTION; AMINES; COMPUTER SIMULATION; DERIVATIVES; FLUORESCENCE; OPTICAL SYSTEMS; PHOTOSENSITIVITY;

PHOTOCHEMICAL REACTIONS;

EID: 27544474616     PISSN: 09599428     EISSN: 13645501     Source Type: Journal    
DOI: 10.1039/b508732e     Document Type: Article

References (82)

1. (a) P. N. Prasad, Introduction to Biophotonics, Wiley-Interscience, New York, 2003;
2. (b) P. N. Prasad, Nanophotonics, Wiley-Interscience, New York, 2004.
3. K. Horie, H. Ushiki and F. M. Winnik, Molecular Photonics, Wiley-VCH, Weinheim, 2000.
4. (a) G. H. Dorion and A. F. Wiebe, Photochromism, Focal Press, New York, 1970;
5. (b) G. H. Brown, Photochromism, Wiley, New York, 1971;
6. (c) A. V. El'tsov, Organic Photochromes, Consultants Bureau, New York, 1990;
7. (d) Photochromism: Molecules and Systems, ed. H. Bouas-Laurent and H. Dürr, Elsevier, Amsterdam, 1990;
8. (e) Organic Photochromic and Thermochromic Compounds, ed. J. C. Crano and R. Guglielmetti, Plenum Press, New York, 1999.
9. (a) C. B. McArdle, Applied Photochromic Polymer Systems, Blackie, Glasgow, 1992;
10. (b) M. Irie, Photo-Reactive Materials for Ultrahigh Density Optical Memory; Elsevier, Amsterdam, 1994;
11. (c) M. Irie, Chem. Rev., 2000, 100, 1683.
12. T. Saika, T. Iyoda, K. Honda and T. Shimidzu, J. Chem. Soc., Chem. Commun., 1992, 591.
13. (a) J. Walz, K. Ulrich, H. Port, H. C. Wolf, J. Wonner and F. Effenberg, Chem. Phys. Lett., 1993, 213, 321;
14. (b) M. Seibold, H. Port and H. C. Wolf, Mol. Cryst. Liq. Cryst., 1996, 283, 75;
15. (c) H. Port, M. Hennrich, M. Seibold and H. C. Wolf, Proc. Electrochem. Soc., 1998, 98, 61;
16. (d) H. Port, A. Hartschuh, M. Hennrich, H. C. Wolf, J. M. Endtner and F. Effenberger, Mol. Cryst. Liq. Cryst., 2000, 344, 145;
17. (e) I. B. Ramsteiner, A. Hartschuh and H. Port, Chem. Phys. Lett., 2001, 343, 83.
18. (a) G. M. Tsivgoulis and J.-M. Lehn, Angew. Chem., Int. Ed. Engl., 1995, 34, 1119;
19. (b) G. M. Tsivgoulis and J.-M. Lehn, Chem. Eur. J., 1996, 2, 1399;
20. (c) A. Fernández-Acebes and J.-M. Lehn, Adv. Mater., 1998, 10, 1519;
21. (d) A. Fernández-Acebes and J.-M. Lehn, Chem. Eur. J., 1999, 5, 3285.
22. (a) H. Spreitzer and J. Daub, Liebigs Ann., 1995, 1637;
23. (b) J. Daub, M. Beck, A. Knorr and H. Spreitzer, Pure Appl. Chem., 1996, 68, 1399.
24. (a) T. B. Norsten and N. R. Branda, Adv. Mater., 2001, 13, 347;
25. (b) A. J. Myles and N. R. Branda, J. Am. Chem. Soc., 2001, 123, 177;
26. (c) T. B. Norsten and N. R. Branda, J. Am. Chem. Soc., 2001, 123, 1784;
27. (d) A. J. Myles and N. R. Branda, Adv. Funct. Mater., 2002, 12, 167.
28. S. Tsuchiya, J. Am. Chem. Soc., 1999, 121, 48.
29. D. R. Reddy and B. G. Maiya, Chem. Commun., 2001, 117.
30. (a) J. L. Bahr, G. Kodis, L. de la Garza, S. Lin, A. L. Moore, T. A. Moore and D. Gust, J. Am. Chem. Soc., 2001, 123, 7124;
31. (b) J. Andréasson, G. Kodis, Y. Terazono, P. A. Liddell, S. Bandyopadhyay, R. H. Mitchell, T. A. Moore, A. L. Moore and D. Gust, J. Am. Chem. Soc., 2004, 126, 15926;
32. (c) Y. Terazono, G. Kodis, J. Andréasson, G. Jeong, A. Brune, T. Hartmann, H. Dürr, T. A. Moore, A. L. Moore and D. Gust, J. Phys. Chem. B, 2004, 108, 1812.
33. (a) T. Kawai, T. Sasaki and M. Irie, Chem. Commun., 2001, 711;
34. (b) A. Osuka, D. Fujikane, H. Shinmori, S. Kobatake and M. Irie, J. Org. Chem., 2001, 66, 3913;
35. (c) K. Yagi, C. F. Soong and M. Irie, J. Org. Chem., 2001, 66, 5419;
36. (d) M.-S. Kim, T. Kawai and M. Irie, Opt. Mater., 2002, 21, 271;
37. (e) L. Giordano, T. M. Jovin, M. Irie and E. A. Jares-Erijman, J. Am. Chem. Soc., 2002, 124, 7481;
38. (f) M. Irie, T. Fukaminato, T. Sasaki, N. Tamai and T. Kawai, Nature, 2002, 420, 759;
39. (g) M.-S. Kim, T. Kawai and M. Irie, Opt. Mater., 2002, 275;
40. (h) T. Fukaminato, T. Sasaki, T. Kawai, N. Tamai and M. Irie, J. Am. Chem. Soc., 2004, 126, 14843.
41. X. Guo, D. Zhang, Y. Zhou and D. Zhu, J. Org. Chem., 2003, 68, 5681.
42. (a) Y. Liang, A. S. Dvornikov and P. M. Rentzepis, Opt. Commun., 2003, 223, 61;
43. (b) Y. Liang, A. S. Dvornikov and P. M. Rentzepis, Proc. Natl. Acad. Sci. U. S. A., 2003, 100, 8109;
44. (c) Y. Liang, A. S. Dvornikov and P. M. Rentzepis, J. Phys. Chem. B, 2004, 108, 8652;
45. (d) A. S. Dvornikov, Y. Liang and P. M. Rentzepis, J. Mater. Chem., 2005, 15, 1072.
46. J. Otsuki, A. Suka, K. Yamazaki, H. Abe, Y. Araki and O. Ito, Chem. Commun., 2004, 1290.
47. S.-J. Lim, B.-K. An, S. D. Jung, M. A. Chung and S. J. Park, Angew. Chem., Int. Ed., 2004, 43, 6346.
48. (a) C.-C. Ko, L.-X. Wu, K. M.-C. Wong, N. Zhu and V. W.-W. Yam, Chem. Eur. J., 2004, 10, 766;
49. (b) V. W.-W. Yam, C.-C. Ko and N. Zhu, J. Am. Chem. Soc., 2004, 126, 12734.
50. R. T. Jukes, V. Adamo, F. Hartl, P. Belser and L. De Cola, Inorg. Chem., 2004, 43, 2779.
51. M. Frigoli, C. Welch and G. Mehl, J. Am. Chem. Soc., 2004, 126, 15382.
52. E. J. Harbron, D. A. Vicente and M. T. Hoyt, J. Phys. Chem. B, 2004, 108, 18789.
53. M. Jin, R. Lu, C. Y. Bao, T. H. Xu and Y. Y. Zhao, Opt. Mater., 2004, 26, 85.
54. (a) F. M. Raymo and S. Giordani, Org. Lett., 2001, 3, 1833;
55. (b) F. M. Raymo and S. Giordani, J. Am. Chem. Soc., 2002, 124, 2004;
56. (c) F. M. Raymo, Spectrum, 2004, 17, 14;
57. (d) M. Tomasulo, S. Giordani and F. M. Raymo, Adv. Funct. Mater., 2005, 15, 787.
58. (a) R. C. Bertelson, in ref. 3b, p. 45;
59. (b) A. S. Kholmanskii and K. M. Dyumanev, Russ. Chem. Rev., 1987, 56, 136;
60. (c) R. Guglielmetti, in ref. 3d, pp. 314 and 855;
61. (d) R. C. Bertelson, in ref. 3e, vol. 1, p. 11;
62. (e) G. Berkovic, V. Krongauz and V. Weiss, in ref. 4c, p. 1741;
63. (f) N. Tamai and H. Miyasaka, in ref. 4c, p. 1875;
64. (g) V. I. Minkin, Chem. Rev., 2004, 104, 2751.
65. L. Purcell, CD-RIDVD: Disc Recording Demystified, McGraw-Hill, New York, 2000.
66. M. Tomasulo, S. Sortino and F. M. Raymo, Org. Lett., 2005, 7, 1109.
67. E. Norambuena, C. Olea-Azar, A. M. Rufs and M. V. Encinas, Phys. Chem. Chem. Phys., 2004, 6, 1230.
68. The quantum yield for the reaction between OX and triethanolamine is too low for the implementation of the device configuration in Fig. 1. As a result, we have not studied this photochemical process in polymer matrices. Instead, we have focused our attention on the photoinduced reaction between OX and triethylamine, which is significantly more efficient.
69. (a) K. Sasaki and T. Nagamura, J. Appl. Phys., 1998, 83, 2894;
70. (b) B. Sae-Lao and R. Soufli, Appl. Opt., 2002, 41, 7309.
71. (a) W. E. Moerner and S. M. Silence, Chem. Rev., 1994, 94, 127;
72. (b) Y. Zhang, R. Burzynsky, S. Ghosal and M. K. Casstevens, Adv. Mater., 1996, 8, 111;
73. (c) W. E. Moerner, A. Grunnet-Jepsen and C. L. Thompson, Annu. Rev. Mater. Sci., 1997, 27, 585;
74. (d) S. J. Zilker, ChemPhysChem, 2000, 1, 72;
75. (e) F. Würthner, R. Wortman and K. Meerholz, ChemPhysChem, 2002, 3, 17;
76. (f) O. Ostroverkhova and W. E. Moerner, Chem. Rev., 2004, 104, 3267.
77. (a) M. Irie, in ref. 4c, p. 1685;
78. (b) N. Hampp, in ref. 4c, p. 1755;
79. (c) J. A. Delaire and K. Nakatani, in ref. 4c, p. 1817;
80. (d) A. Natansohn and P. Rochon, Chem. Rev., 2002, 102, 4139.
81. The emitted radiation is not sufficiently intense to encourage the photochemical reaction between OX and triethylamine. Consistently, the state of the photosensitive layer does not change significantly even after thousands of emission readings.
82. The detected emission intensity decreases by ca. 2% after 1000 excitation cycles. It follows that ca. 6610 excitation cycles would, presumably, lower the detected intensity to the logic threshold. Thus, a binary 0 cannot be read more than 6610 times. In principle, this limitation can be overcome by selecting a fluorophore with an excitation wavelength in a spectral region where the photosensitive layer does not absorb.