Exploring the emissive properties of New Azacrown compounds bearing aryl, furyl, or thienyl moieties: A special case of chelation enhancement of fluorescence upon interaction with Ca2+, Cu2+, or Ni 2+

Inorganic Chemistry

Volumn 49, Issue 23, 2010, Pages 10847-10857

  Oliveira, Elisabete ^a   Baptista, Rosa M F ^b   Costa, Susana P G ^b   Raposo, M Manuela M ^b   Lodeiro, Carlos ^a,c  

^a UNIVERSIDADE NOVA DE LISBOA   (Portugal)

^b UNIVERSITY OF MINHO   (Portugal)

^c UNIVERSITY OF VIGO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CALCIUM; CHELATING AGENT; COPPER; CROWN COMPOUND; FLUORESCENT DYE; IMIDAZOLE DERIVATIVE; METAL; NICKEL;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ELECTRON SPIN RESONANCE; MASS SPECTROMETRY; SPECTROFLUOROMETRY; SPECTROPHOTOMETRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CALCIUM; CHELATING AGENTS; COPPER; CROWN COMPOUNDS; CRYSTALLOGRAPHY, X-RAY; ELECTRON SPIN RESONANCE SPECTROSCOPY; FLUORESCENT DYES; IMIDAZOLES; METALS; MODELS, MOLECULAR; NICKEL; SPECTROMETRY, FLUORESCENCE; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; SPECTROPHOTOMETRY;

EID: 78650246295     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic101095y     Document Type: Article

References (108)

1. Czarnik, A. W. Acc. Chem. Res. 1994, 27, 302-308
2. Czarnik, A. W. Acc. Chem. Res. 1998, 31, 201-207
3. Ulijn, R. V. and Smith, A. M. Chem. Soc. Rev. 2008, 37, 664-675
4. Cavalli, S., Albericio, F., and Kros, A. Chem. Soc. Rev. 2010, 39, 241-263
5. Sawada, T., Takahashi, T., and Mihara, H. J. Am. Chem. Soc. 2009, 131 (40) 14434-14441
6. Lodeiro, C. and Pina., F. Coord. Chem. Rev. 2009, 253, 1353-1383
7. Prodi, L, Bolleta, F., Montalti, M., and Zaccheroni, N. Coord. Chem. Rev. 2000, 205, 59-83
8. Martínez-Mañez, M. and Sanceno, F. Chem. Rev. 2003, 103, 4419-4476
9. Jiang, P. J. and Guo, Z. J. Coord. Chem. Rev. 2004, 248, 205-229
10. Finney, N. S. Current Opp. Chem. Biol. 2006, 10, 238-245
11. Lörh, H. G. and Vögtle, F. Acc. Chem. Res. 1985, 18, 65-72
12. Okamoto, H., Owari, M., Kimura, M., and Satake, K. Tetrahedron Lett. 2001, 42, 7453-7455
13. Debus, H. Liebigs Ann. Chem. 1858, 107, 199-208
14. Siddiqui, S. A., Narkhede, U. C., Palimkar, S. S., Daniel, T., Rajgopal, J. L., and Srinivasan, K. V. Tetrahedron 2005, 61, 3539-3546 and references therein
15. Bellina, F., Cauteruccio, S., and Rossi, R. Tetrahedron 2007, 63, 4571-4624 and references therein.
16. Moylan, C. R., Miller, R. D., Twieg, R. J., Betterton, K. M., Lee, V. Y., Matray, T. J., and Nguyen, C. Chem. Mat. 1993, 5, 1499
17. Bu, X. R., Li, H. Y., VanDerveer, D., and Mintz, E. A. Tetrahedron Lett. 1996, 37, 7331
18. Santos, J., Mintz, E. A., Zehnder, O., Bosshard, C., Bu, X. R., and Gunter, P. Tetrahedron Lett. 2001, 42, 805
19. Wang, S., Zhao, L., Xu, Z., Wu, C., and Cheng, S. Mater. Letters 2002, 56, 1035
20. Wu, W., Ye, C., and Wang, D. Arkivoc 2003, 59
21. Wu, W., Zhang, Z., and Zhang, X. J. Chem. Res. 2004, 9, 617
22. Wu, W., Zhang, Z. L., and Zhang, X. Y. J. Nonlinear Opt. Phys. Mater. 2005, 14, 61
23. Ren, J., Wang, S. M., Wu, L. F., Xu, Z. X., and Dong, B. H. Dyes Pigments 2008, 76, 310
24. Batista, R. M. F., Costa, S. P. G., Belsley, M., Lodeiro, C., and Raposo, M. M. M. Tetrahedron 2008, 64, 9230
25. Batista, R. M. F., Costa, S. P. G., Belsley, M., and Raposo, M. M. M. Dyes Pigments 2009, 80, 329
26. Feng, K., Hsu, F. L., Bota, K., and Bu, X. R. Microchem J. 2005, 81, 23
27. Zhang, M., Li, M., Zhao, Q., Li, F., Zhang, D., Zhang, J., Yi, T., and Huang, C. Tetrahedron Lett. 2007, 48, 2329
28. Zhang, M., Li, M. Y., Li, F. Y., Cheng, Y. F., Zhang, J. P., Yi, T., and Huang, C. H. Dyes Pigments 2008, 77, 408
29. Feng, K., De Boni, L., Misoguti, L., Mendonca, C. R., Meador, M., Hsu, F. L., and Bu, X. R. Chem. Commun. 2004, 1178
30. Zhao, L., Li, S. B., Wen, G. A., Peng, B., and Huang, W. Mater. Chem. Phys. 2006, 100, 460
31. Fang, Z., Wang, S., Zhao, L., Xu, Z., Ren, J., Wang, X., and Yang, Q. Mater. Chem. Phys. 2008, 107, 305
32. Pina, J., Seixas de Melo, J., Batista, R. M. F., Costa, S. P. G., and Raposo, M. M. M. J. Phys. Chem. B 2010, 114, 4964
33. Feng, K., Hsu, F. L., Van DerVeer, D., Bota, K., and Bu, X. R. J. Photochem. Photobiol. A-Chem. 2004, 165, 223
34. De Silva, A. P., Gunaratne, H. Q. N., Gunnlaugsson, T., Huxley, A. J. M., McCoy, C. P., Rademacher, J. T., and Rice, T. E. Chem. Rev. 1997, 97, 1515-1566
35. Bolletta, F., Costa, I., Fabbrizzi, L., Licchelli, M., Montalti, M., Pallavicini, P., Prodi, L., and Zaccheroni, N. J. Chem. Soc., Dalton Trans. 1999, 1381-1386
36. Goldsmith, C. R. and Lippard, S. J. Inorg. Chem. 2006, 45, 6474-6478
37. Wu, D., Huang, W., Duan, C., Zhihua, L., and Meng, Q. Inorg. Chem. 2007, 46, 1538-1540
38. Alarcon, J., Albelda, M. T., Belda, R., Clares, M. R., Delgado-Pinar, E., Frias, J. C., García-España, E., González, J., and Soriano, C. Dalton Trans. 2008, 46, 6530-6538
39. Mameli, M., Aragoni, M. C., Arca, M., Caltagirone, C., Demartin, F., Farrugia, G., De Filippo, G., Devillanova, F. A., Garau, A., Isaia, F., Lippolis, V., Murgia, S., Prodi, L., Pintus, A., and Zaccheroni, N. Chem. - Eur. J. 2010, 16, 919-930
40. Rurack, K. Spectrochim. Acta A 2001, 57, 2161-2195
41. Kim, J., Morozumi, T., and Nakamura, H. Org. Lett. 2007, 9, 4419-4422
42. Magri, D. C., Callan, J. F., de Silva, A. P., Fox, D. B., McClenaghan, N. D., and Sandanayake, K. R. A. S. J. Fluoresc. 2005, 15, 769-775
43. Vysotski, E. S. and Lee, J. Acc. Chem. Res. 2004, 37, 405-415
44. Parkers, R., Mohsin, S., Lee, T. C., and Gunnlaugsson, T. Chem. Mater. 2007, 19, 1656-1663
45. Gerencser, A. A. and Adam-Vizi, V. Cell Calcium 2001, 30, 311-321
46. Boiocchi, M., Fabbrizzi, L., Licchelli, M., Sacchi, D., Vázquez, M., and Zampa, C. Chem. Commun. 2003, 1812-1813
47. Anda, C., Bazzicalupi, C., Bencini, A., Bianchi, A., Fornasari, P., Giorgi, C., Valtancoli, B., Lodeiro, C., Parola, A. J., and Pina., F. Dalton Trans. 2003, 1299-1307
48. Nuñez, C., Bastida, R., Macias, A., Bértolo, E., Fernandes, L., Capelo, J. L., and Lodeiro, C. Tetrahedron 2009, 65, 6179-6188
49. Tamayo, A., Lodeiro, C., Escriche, L., Casabo, J., Covelo, B., and González, P. Inorg. Chem. 2005, 44, 8105-8115
50. Fernandes, L., Boucher, M., Fernández-Lodeiro, J., Oliveira, E., Nuñez, C., Santos, H. M., Capelo, J. L., Faza, O. N., Bértolo, E., and Lodeiro, C. Inorg. Chem. Commun. 2009, 12, 905-912
51. Aragoni, M. C., Arca, M., Bencini, A., Blake, A. J., Caltagirone, C., Decortes, A., Demartin, F., Devillanova, F. A., Faggi, E, Dolci, L. S., Garau, A., Isaia, F., Lipplis, V., Prodi, L., Valtancoli, B., and Zaccheroni, N. Dalton Trans. 2005, 2994-3004
52. Yu, M., Shi, M., Chen, Z., Li, F., Li, X., Gao, Y., Xu, J., Yang, H., Zhou, Z., Yi, T., and Huang, C. Chem. - Eur. J. 2008, 14, 6892-6900
53. Xu, Z., Xiao, Y., Qian, X., Cui, J., and Cui, D. Org. Lett. 2005, 7, 889-892
54. Chem, X. Q., Jia, J., Ma, H. M., Wang, S. J., and Wang, X. C. Anal. Chim. Acta 2009, 1, 9-14
55. Wang, H. X., Wang, D. L., Wang, Q., Li, X. Y., and Schalley, C. A. Org. Biomol. Chem. 2010, 8, 1017-1026
56. Yang, Y. K., Yook, K. J., and Tae, J. J. Am. Chem. Soc. 2005, 127, 16760-16761
57. Zhang, G., Zhang, D., Yin, S., Yang, X., Shuai, Z., and Zhu, D. Chem. Commun. 2005, 16, 2161-2163
58. Guo, X., Qian, X., and Jia, L. J. Am. Chem. Soc. 2004, 126, 2272-2273
59. Nolan, E. M. and Lippard, S. J. J. Am. Chem. Soc. 2003, 125, 14270-14721
60. Hennrich, G., Walther, W., Resch-Genger, U., and Sonnenshein, H. Inorg. Chem. 2001, 40, 641-644
61. Zhao, Y., Lin, Z., He, C., Wu, H., and Duan, C. Inorg. Chem. 2006, 45, 10013-10015
62. Shamsipur, M., Hosseini, M., Alixadeh, K., Alizadeh, N., Yari, A., Caltagirone, C., and Lippolis, V. Anal. Chim. Acta 2005, 353, 17-24
63. Goretzki, G., Bonnesen, P. V., Dabestain, R., and Brown, G. M. ACS Symp. Ser. 2008, 943, 13-33
64. Al-Kady, A. S., Gaber, M., Hussein, M. M., and Ebeid, E. Z.M. J. Phys. Chem. A. 2009, 34, 9474-9478
65. Lee, Y. J., Seo, D., Kwom, J. Y., Son, G., Park, M. S., Choi, Y.-H., Soh, J. H., Lee, H. N., Lee, K. D., and Yoon, J. Tetrahedron 2006, 62, 12340-12344
66. Chandrasekhar, V., Bag, P., and Pandey, M. D. Tetrahedron 2009, 65, 9876-9883
67. Batista, R. M. F., Oliveira, E., Nuñez, C., Costa, S. P. G., Lodeiro, C., and Raposo, M. M. M. J. Phys. Org. Chem. 2009, 22, 362-366
68. Pedras, B., Fernandes, L., Oliveira, E., Rodriguez, L., Raposo, M. M. M., Capelo, J. L., and Lodeiro, C. Inorg. Chem. Commun. 2009, 12, 79-85
69. Batista, R. M. F., Oliveira, E., Costa, S. P. G., Lodeiro, C., and Raposo, M. M. M. Org. Lett. 2007, 9, 3201-3204
70. Costa, S. P. G., Oliveira, E., Lodeiro, C., and Raposo, M. M. M. Sensors 2007, 7, 2096-2114
71. Lodeiro, C., Capelo, J. L., Mejuto, J. C., Oliveira, E., Santos, H. M., Pedras, B., and Nuñez, C. Chem. Soc. Rev. 2010, 39, 2948-2976
72. Raposo, M. M. M., García-Acosta, B., Ábalos, T., Martínez-Manez, R., Ros-Lis, J. V., and Soto, J. J. Org. Chem. 2010, 75, 2922-2933
73. Berlman, I. B. Handbook of Fluorescence Spectra of Aromatic Molecules, 2 nd ed.; Academic Press: New York, 1971.
74. Montalti, L., Credi, A., Prodi, T., and Gandolfi, M. T.; Handbook of Photochemistry, 3 rd ed.; Taylor and Francis Group: Boca Ratón, FL, 2006.
75. SMART: Instrument Control and Data Collection Software, version 5.054; Bruker Analytical X-ray Systems Inc.: Madison, WI, 1997.
76. SAINT: Data Integration software package, version 6.01; Bruker Analytical X-ray Systems Inc.: Madison, WI, 1997.
77. Sheldrick, G. M. SADABS. A Computer Program for Absorption Corrections; University of Göttingen: Göttingen, Germany, 1996.
78. Sheldrick, G. M. SHELXS97. A Computer Program for the Solution of Crystal Structures from X-ray Data; University of Göttingen: Göttingen, Germany, 1997.
79. Sheldrick, G. M. SHELXL97. A Computer Program for the Refinement of Crystal Structures from X-ray Data; University of Göttingen: Göttingen, Germany, 1997.
80. Spek, A. L. PLATON. A Multipurpose Crystallographic Tool; Utrecht University; Utrecht, The Netherlands, 2001.
81. Qin, W., Baruah, M., Silwa, M., Van der Auweraer, M., De Borggraeve, W. M., Beljonne, D., Averbeke, B. V., and Boens, N. J. Phys. Chem. A 2008, 112, 6104-6114
82. Davidson, D., Weiss, M., and Jelling, M. J. J. Org. Chem. 1937, 2, 319-327
83. Nakamoto, K. Infrared and Raman Spectra of Inorganic and Coordination Compounds, 3 rd ed.; Wiley-Interscience: New York, 1978.
84. Peng, S. M., Gordon, G. C., and Goedken, V. L. Inorg. Chem. 1978, 17, 119-126
85. Costa, S. P. G., Oliveira, E., Lodeiro, C., and Raposo, M. M. M. Tetrahedron Lett. 2008, 49, 5258-5261
86. Batista, R. M. F., Oliveira, E., Costa, S. P. G., Lodeiro, C., and Raposo, M. M. M. Tetrahedron Lett. 2008, 49, 6575-6578
87. Saleh, A., Al-Soud, Y. A., and Nau, W. M. Spectrochim. Acta, Part A 2008, 71, 818-822
88. Lodeiro, C., Parola, A. J., Pina, F., Bazzicalupi, C., Bencini, A., Bianchi, A., Giorgi, C., Masotti, A., and Valtancoli, B. Inorg. Chem. 2001, 40, 2968-2975
89. Bazzicalupi, C., Bencini, A., Berni, E., Bianchi, A., Danesi, A., Giorgi, C., Valtancoli, B., Lodeiro, C., Lima, J. C., Pina, F., and Bernardo, M. A. Inorg. Chem. 2004, 43, 5134-5146
90. Pina, J., Seixas de Melo, J., Pina, F., Lodeiro, C., Lima, J. C., Parola, A. J., Soriano, C., Clares, M. P., Albelda, M. T., Aucejo, R., and Garcia-España, E. Inorg. Chem. 2005, 44, 7449-7458
91. Pedras, B., Oliveira, E., Santos, H., Rodríguez, L., Crehuet, R., Avilés, T., Capelo, J. L., and Lodeiro, C. Inorg. Chim. Acta 2009, 362, 2627-2635
92. NMR titration experiments were carried out in deuterated DMSO, due to the low solubility of 1 in ethanol at NMR concentration, and showed two protonation steps: a first step involving the azacrown nitrogen and a second step involving the imidazole nitrogen. After protonation, both set of signals were broadned and difficult to differentiate. In this case, the signals attributed to the protonated azacrown nitrogen at 3.9-3.4 ppm were stabilized by increasing addition of protons before the signals attributed to the protonated imidazole nitrogen.
93. Vicente, M., Bastida, R., Lodeiro, C., Macias, A., Parola, A. J., Valancia, L., and Spey, S. E. Inorg. Chem. 2003, 42, 6768-6779
94. Yang, T., Gao, M., Qin, W., and Yang, J. Ind. J. Chem. A. 2010, 49, 45-48
95. Li, R.-J. and Chang, I.-J. J. Chin. Chem. Soc. 2002, 49, 161-164
96. Gokel, G. W., Leevy, W. M., and Weber, M. E. Chem. Rev. 2004, 104, 2723-2750
97. Warmke, H., Wiczk, W., and Ossowski, T. Talanta 2000, 52, 449-456
98. Gans, P., Sabatini, A., and Vacca, A. Talanta 1996, 43, 1739-1753
99. Lever, A. B. P. Inorganic Electronic Spectroscopy; Elsevier: Amsterdam, 1968.
100. Pearson, R. G. J. Am. Chem. Soc. 1963, 22, 3533-3539
101. McClure, D. S. J. Chem. Phys. 1952, 20, 682-686
102. Burress, C. N., Bodine, M. I., Elbjeirami, O., Reibenspies, J. H., Omary, M. A., and Gabbaie, F. P. Inorg. Chem. 2007, 46, 1388-1395
103. Mameli, M., Lippolis, V., Caltagirone, C., Capelo, J. L., Nieto-Faza, O., and Lodeiro, C. Inorg. Chem. 2010, 49 (18) 8276-8286 10.1021/ic1007439
104. Tamayo, A., Pedras, B., Lodeiro, C., Escriche, L., Casabó, L., Capelo, J. L., Covelo, B., Kivekäs, R., and Sillanpaä, R. Inorg. Chem. 2007, 46, 7818-7826
105. Beloglazkina, E. Z., Shimorsky, A. V., Mazhuga, A. G., Shilova, O. V., Tafeenko, V. A., and Zyk, N. V. Rus. J. Gen. Chem. 2009, 79, 1504-1508
106. Milne, J. B. Can. J. Chem. 1970, 48, 75-79
107. Strange, A. F., Klein, A., Klinkhammer, K.-W., and Kaim, W. Inorg. Chim. Acta 2001, 324, 336-341
108. Rapenne, G., Dietrich-Buchecker, C., and Sauvage, J.-P. J. Am. Chem. Soc. 1999, 121, 994-1001