Molecular photoionic switches with an internal reference channel for fluorescent pH sensing applications

New Journal of Chemistry

Volumn 20, Issue 7-8, 1996, Pages 871-880

  De Prasanna Silva, A ^a   Nimal Gunaratne, H Q ^a   Gunnlaugsson, Thorfinnur ^a   Mark Lynch, P L ^a  

^a QUEEN'S UNIVERSITY BELFAST   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001092462     PISSN: 11440546     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (114)

1. Supramolecular Photochemistry, Balzani V. Ed., Reidel, Dordrecht, 1987.
2. Balzani V., Scandola F., Supramolecular Photochemistry, Ellis-Horwood, Chichester, 1991.
3. Fox M. A., Adv. Photochem., 1986, 13, 238;
4. Mauzerall D. C. in Photoinduced Electron Transfer. Part, A. Fox M. A., Chanon M. Eds. Elsevier, Amsterdam, 1988, p. 228;
5. Kavarnos G. J., Fundamentals of Photoinduced Electron Transfer, VCH, New York, 1993.
6. Gust D., Moore T. A., Top. Curr. Chem., 1991, 159, 103;
7. Moore T. A., Gust D., Mathis P., Mialocq J.-C., Chachaty C., Bensasson R. V., Land E. J., Doizi D., Liddell P. A., Lehman W. R., Nemeth G. A., Moore A. L., Nature, 1984, 307, 630;
8. Gust D., Moore T. A., in The Photosynthetic Reaction Center. Vol. II, Deisenhofer J., Noms J. R. ed., Academic, San Diego, 1993, p.419;
9. Gust D., Moore T. A., Moore A. L., Acc. Chem. Res., 1993, 26, 198.
10. Maruyama K., Osuka A., Malaga N., Pure Appl. Chem., 1994. 66, 867;
11. Osuka A., Yamada Y., Malaga N., Chem. Lett., 1995, 591.
12. Sauvage J. P., Collin J. P., Chambron J. C., Guillerez S., Coudrel C., Balzani V., Barigelletli F., de Cola L., Flamigni L., Chem. Rev., 1994, 94, 993.
13. Danielson E., Elliol C. M., Merken J. W., Meyer T. J., J. Am. Chem. Soc., 1987, 109, 2519.
14. Wasielewski M. R., Chem. Rev., 1992, 92, 435.
15. Wagner R. W., Lindsey J. S., J. Am. Chem. Soc., 1994, 116, 9759.
16. Jullien L., Canceill J., Valeur B., Bardez E., Lehn J. M., Angew. Chem.. Int. Ed. Engl., 1994, 33, 2438.
17. Balzani V., Campagna S., Denti G., Juris A., Serroni S., Venturi M., Solar Energy Mater, Solar Cells, 1995, 38, 159.
18. The Photosynthetic Reaction Center. Vols. I and II, Deisenhofer J., Morris J. R. Eds., Academic, San Diego, 1993.
19. Bryan A. J., de Silva A. P., de Silva S. A., Rupasinghe R. A. D. D., Sandanayake K. R. A. S., Biosensors, 1989, 4, 169;
20. Bissell R. A., de Silva A. P., Gunaratne H. Q. N., Lynch P. L. M., Maguire G. E. M., Sandanayake K. R. A. S., Chem. Soc. Rev., 1992, 21, 187;
21. Bissell R. A., de Silva A. P., Gunaratne H. Q. N., Lynch P. L. M., Maguire G. E. M., McCoy C. P., Sandanayake K. R. A. S., Top. Curr. Chem., 1993, 168, 223.
22. Czarnik A. W., Adv. Supramol. Chem., 1993, 3, 131;
23. Czarnik A. W., Acc. Chem. Res., 1994, 27, 302.
24. The research of several laboratories world-wide are summarized in Fluorescent Chemosensors for Ion and Molecule Recognition, Czarnik A. W. Ed., ACS Symp. Ser., 1993, 538.
25. Valeur B. in Probe Design and Chemical Sensing. Topics in Fluorescence Spectroscopy. Vol. 4. Lackowicz J. R. Ed., Plenum, New York 1994, p.21;
26. Valeur B., Bardez E., Chem. Brit., 1995, 31, 216.
27. Fabrizzi L., Poggi A., Chem. Soc. Rev., 1995, 24, 197.
28. De Silva A. P., Rupasinghe R. A. D. D., J. Chem. Soc., Chem. Commun., 1985, 1669;
29. Bissell R. A., Calle E., de Silva A. P., de Silva S. A., Gunaratne H. Q. N., Habib-Jiwan J. L., Peiris S. L. A., Rupasinghe R. A. D. D., Samarasinghe T. K. S. D., Sandanayake K. R. A. S., Soumillion J.-P., J. Chem. Soc., Perkin Trans., 2, 1992, 1559.
30. Huston M. E., Haider K. W., Czarnik A. W., J. Am. Chem. Soc., 1988, 110, 4460.
31. Ibemesi J. A., El-Bayoumi M. A., Mol. Photochem., 1979, 9, 243;
32. Gubelmann M., Harriman A., Lehn J.-M., Sessler J. L., J. Chem. Soc., Chem.Commun., 1988, 77;
33. Van Arman S. A., Czarnik A. W., J. Am. Chem. Soc.. 1990, 112, 5376;
34. Grigg R., Norbert W. D. J. A., J. Chem. Soc., Chem. Commun., 1992, 1300;
35. Bemado M. A., Parola A.J ., Pinas F., Garcia-Espana E., Marcelino V., Luis S. V., Miravet J. F., J. Chem. Soc., Dalton Trans., 1995, 993.
36. De Silva A. P., Sandanayake K. R. A. S., Angew. Chem., Int. Ed. Engl., 1990,29, 1173.
37. James T. D., Sandanayake K. R. A. S., Shinkai S., Nature, 1995, 374, 345;
38. James T. D., Sandanayake K. R. A. S., Shinkai S., Angew. Chem., Int. Ed. Engl., 1994, 33, 2207.
39. Vance D. H., Czarnik A. W., J. Am. Chem. Soc., 1994, 116, 9397.
40. Pages F., Desvergne J.-P., Bouas-Laurent H., Lehn J.-M., Konopelski J.-P., Marsau P., Barrons Y., J. Chem. Soc., Chem. Commun., 1990, 655;
41. Fages F., Desvergne J.-P., Kampke K., Bouas-Laurent H., Lehn J.-M., Meyer M., Albrecht-Gary A.-M., J. Am. Chem. Soc., 1993, 115, 3658.
42. Sandanayake K. R. A. S., James T. D., Shinkai S., Chem. Lett., 1995, 503.
43. De Silva A. P., Gunaratne H. Q. N., McCoy C. P., Nature, 1993, 364, 42.
44. For an interesting variation, see; Iwata S., Tanaka K., J. Chem. Soc., Chem. Commun.. 1995, 1491.
45. Progress toward all-optical AND logic gates; O'Neil M. P., Niemczyk M. P., Svec W. A., Gosztola D., Graines G. L., Wasielewski M. R., Science, 1992, 257,63.
46. Birge R. R. in Nanotechnology. Research and Perspectives. Crandall B. C., Lewis J. Ed., MIT Press, Cambridge, 1992, p. 149.
47. Mes G. F., Van Ramesdonk H. J., Verhoeven J. W., J. Am. Chem. Soc.. 1984, 106, 1335.
48. De Suva A. P., Gunaratne H. Q. N., Kane A. T. M., Maguire G. E. M., Chem. Lett., 1995, 125.
49. Tsien R. Y., Minta A., EUT. Pat., 1989, 0 314 480A2.
50. Kühn M. A., ACS Symp. Ser., 1993, 538, 147.
51. Wang Y. C., Morawetz H., J. Am. Chem. Soc., 1976, 98, 3611.
52. Beddard G. S., Davidson R. S., Whelan T. D., Chem. Phys. Lett., 1977, 56, 54.
53. De Cola L., Balzani V., Barigelletti F., Flamigni L., Belser P., Von Zelewsky A., Frank M., Vogtle F., Inorg. Chem., 1993, 32, 5220.
54. Scandola F., Indelli M. T., Chiorboli C., Bignozzi C. A., Top. Curr. Chem., 1990, 158, 73.
55. Wilkinson F. in Photoindttced Electron Transfer. Part A. Fox M. A., Chanon M. Eds., Eisevier, Amsterdam, 1988, p. 207.
56. For a recent case involving an all-organic supermolecule, see; Clayton A. H. A., Ghiggino K. P., Lawson J. M., Paddon-Row M. N., J. Photochem. Photobiol. A: Chem., 1994, 80, 323.
57. De Silva A. P., de Silva S. A., J. Chem. Soc., Chem. Commun., 1986, 1709.
58. De Silva A. P., de Silva S. A., Dissanayake S. A., Sandanayake K. R. A. S., J. Chem. Soc., Chem. Commun., 1989, 1054.
59. De Silva A. P., Sandanayake K. R. A. S., J. Chem. Soc., Chem. Commun., 1989, 1183.
60. De Silva A. P., Gunaratne H. Q. N., J. Chem. Soc., Chem. Commun., 1990, 186.
61. De Silva A. P., Gunaratne H. Q. N., Maguire G. E. M., J. Chem. Soc., Chem. Commun., 1994, 1231.
62. Bright G. B., Fisher G. W., Rogowska J., Taylor D. L., Meth. Cell. Biol., 1989, 30, 157.
63. Kano K., Pendler J. H., Biochem. Biophys. Acta, 1978, 509, 289.
64. Martin M. M., Plaza P., Hung N. D., Meyer Y. H., Bourson J., Valeur B., Chem. Phys. Lett., 1993, 202, 425.
65. Letard J. F., Lapouyade R., Rettig W., Pure Appl. Chem., 1993,65, 1705;
66. Dumon P., Jonusauskas G., Dupuy F., Pee P., Rulliere C., Letard J. F., Lapouyade R., J. Phys. Chem., 1994, 98, 10391.
67. Grynkiewicz G., Poenie M., Tsien R. Y., J. Biol. Chem., 1985, 260, 3440.
68. Tsien R. Y., Chem. Eng. News, 1994, July 18, 34.
69. Tsien R. Y., Ann. Rev. Biophys. Bioeng., 1983, 12, 91.
70. Whitaker J. E., Haugland R. P., Prendergast F. G., Anal. Biochem., 1991, 194, 330.
71. Ireland J. F., Wyatt P. A. H., Adv. Phys. Org. Chem., 1976, 12, 131;
72. KosowerE. M., Huppert D.,Ann. Rev. Phys. Chem., 1986, 37, 127.
73. Valeur B. in Fluorescent Biomolecules: Methodologies and Applications, Jameson D. M., Reinhart G. D. Ed., Plenum, New York, 1989, p. 269.
74. Mugnier J., Pouget J., Bourson J., Valeur B., J. Luminescence, 1985, 33, 273.
75. Closs G. L., Miller J. R., Science, 1988, 240, 440.
76. Harriman A. in Supramolecular Photochemistry, Balzani V. Ed., Reidel, Dordrecht, 1987, p. 207.
77. Beeson J. C., Huston M. E., Pollard D. A., Venkatachalam T. K., Czarnik A. W., J. Fluorescence, 1993, 3, 65.
78. Qian X. H., Zhu Z. H., Chen K. C., Dyes Pigm., 1989, 11, 13.
79. Nemeth S., Jao T. C., Pendler J. H., J. Photochem. Photobiol. A. Chem.. 1994, 78, 229.
80. Pardo A., Poyato J. M. L., Camacho J. J., Espelosin R. H., Femandez-Alonso J. L, J. Mol. Struct., 1986, 142, 147.
81. Pardo A., Martin E., Poyato J. M. L., Camacho J. J., Brana M. F., Casteliano J. M., J. Photochem. Photobiol. A. Chem., 1987, 41, 69.
82. Yuan D., Brown R. G., J. Chem. Res. (M), 1994, 2346.
83. De Suva A. P., Gunaratne H. Q. N., Habib-Jiwan J.-L., McCoy C. P., Rice T. E., Soumillion J.-P., Angew. Chem., Int. Ed. Engl., 1995, 34, 1728.
84. Berlman I. B., Handbook of Fluorescence Spectra of Aromatic Molecules. 2nd ed. Academic, New York, 1971.
85. Alexiou M. S., Tychopoulos V., Ghorbanian S., Tyman J. H. P., Brown R. G., Brittain P. I., J. Chem. Soc., Perkin Trans. 2, 1990, 837.
86. Schnepp O., Levy M., J. Am. Chem. Soc., 1962, 84, 172.
87. Tian H., Tang Y., Chen K. C., Dyes Pigm., 1994, 26, 159.
88. Bullpitt M., Kitching W., Doddrell D., Adcock W., J. Org. Chem., 1976, 41, 760.
89. Middleton R. N., Parrick J., Clarke E. D., Wardman P., J. Hetewcycl. Chem., 1986, 23, 849.
90. Ueno A., Suzuki I., Osa T., J. Am. Chem. Soc., 1989, 111, 6391;
91. Kumar C. V., Asuncion E. H., J. Chem. Soc., Chem. Commun., 1992. 470;
92. Kumar C. V., Asuncion E. H., J. Am. Chem. Soc., 1993. 115, 8547.
93. Cain C. C., Murphy R. R, J. Cell. Biol, 1988, 106, 269.
94. Lehn J.-M., Supramolecular Chemistry, VCH, Weinheim, 1995;
95. Lehn J.-M., Angew. Chem., Int. Ed. Engl., 1990, 29, 1304.
96. Amabilino D., Stoddart J. R, New Scientist, 1994, 141, (1913), 25;
97. Dietrich-Buchecker C. O., Nierengarten J. R, Sauvage J.-P., Tetrahedron Lett., 1992, 33, 3625.
98. Turro N. J., Ramamurthy V., Cherry W., Farneth W., Chem. Rev., 1978, 78, 125;
99. Grimshaw J., de Suva A. P., J. Chem. Soc., Perkin Trans 2, 1981, 1010.
100. Brun A. M., Atherton S. J., Harriman A., Heitz V., Sauvage J.-P., J. Am. Chem. Soc., 1992, 114, 4632.
101. lyoda T., Morimoto M., Kawasaki N., Shimidzu T., J. Chem. Soc.; Chem. Commun., 1991, 1480;
102. Martensson J., Sandros K., Wennerstrom O., J. Phys. Org. Chem., 1994, 7, 534;
103. Yoon D. I., Bergbrennan C. A., Lu H., Hupp J. T., Inorg. Chem., 1992, 31, 3192.
104. Belser P., Dux R., Baak M, De Cola L., Balzani V., Angew. Chem., Int. Ed. Engl, 1995, 34, 595;
105. Walz J., Ulrich K., Port H., Wolf H. C., Wonner J., Effenberger F., Chem, Phys. Lett., 1993, 213, 321.
106. The excitation spectral correction in our instrument appears to degrade in quality at shorter wavelengths. The So -52 band of the aminonaphthalimide fluorophore is weaker than expected from its absorption spectrum. Therefore 387 nm (the 0-0 vibrational band position of the anthracene unit) and 410 nm (the absorption maximum of the aminonaphthalimide unit where anthracene is transparent) were the wavelengths used to compare the excitation and absorption spectra. The error would be larger if 367 nm (the 0-1 vibrational band position of the anthracene unit) was used due to the greater separation from 410 nm.
107. Valeur B., Bourson J., Pouget J., Kaschke M, Ernsting N. P., J. Phys. Chem., 1992, 96, 6545.
108. Adams S. R., Harootunian A. T., -Buechler Y. J., Taylor S. S., Tsien R. Y., Nature, 1991, 349, 694.
109. Mann C. K., Barnes K. K., Electrochemical Reactions in Nonaqueous Systems. Dekker, New York, 1970.
110. De Suva A. P., Gunaratne H. Q. N., Lynch P. L. M., J. Chem. Soc., Perkin Trans 2, 1995, 685.
111. Grabowski Z. R., Dobkowski J., Pure Appl. Chem., 1983, 55, 245.
112. Weller A., Pure Appl. Chem., 1968, 16, 115.
113. McCoy C. P., Ph. D. Thesis Queen's University, Belfast, 1994.
114. Birks J. B., Photophysics of Aromatic Molecules, Wiley, New York, 1970.