Bright, fluorescent dyes based on imidazo[1,2-a]pyridines that are capable of two-photon absorption

Chemistry - An Asian Journal

Volumn 8, Issue 6, 2013, Pages 1279-1294

  Firmansyah, Dikhi ^a   Ciuciu, Adina I ^b   Hugues, Vincent ^c   Blanchard Desce, Mireille ^c   Flamigni, Lucia ^b   Gryko, Daniel T ^a,d  

^a WARSAW UNIVERSITY OF TECHNOLOGY   (Poland)

^b CNR   (Italy)

^c UNIVERSITÉ DE BORDEAUX   (France)

^d INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

Author keywords

dyes; fluorescence; nitrogen heterocycles; substituent effects; two photon absorption

Indexed keywords

CHARGE TRANSFER; DYES; ELECTRONS; EXCITED STATES; FLUORESCENCE; OPTICAL PROPERTIES; PHOTONS; PYRIDINE; QUANTUM YIELD;

ELECTRON WITHDRAWING GROUP; ELECTRON-DONATING SUBSTITUENTS; ELECTRON-WITHDRAWING SUBSTITUENTS; LUMINESCENCE QUANTUM YIELDS; NITROGEN HETEROCYCLES; NON-LINEAR OPTICAL PROPERTIES; SUBSTITUENT EFFECT; TWO PHOTON ABSORPTION;

TWO PHOTON PROCESSES;

FLUORESCENT DYE; IMIDAZOLE DERIVATIVE; PYRIDINE DERIVATIVE;

ABSORPTION; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; PHOTON; SPECTROPHOTOMETRY; SYNTHESIS;

ABSORPTION; FLUORESCENT DYES; IMIDAZOLES; MOLECULAR STRUCTURE; PHOTONS; PYRIDINES; SPECTROPHOTOMETRY;

EID: 84878294339     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.201300058     Document Type: Article

References (76)

1. M. Pawlicki, H. A. Collins, R. G. Denning, H. L. Anderson, Angew. Chem. 2009, 121, 3292-3316
2. Angew. Chem. Int. Ed. 2009, 48, 3244-3266
3. H. Meier, Angew. Chem. 2005, 117, 2536-2561
4. Angew. Chem. Int. Ed. 2005, 44, 2482-2506
5. M. Rumi, S. Barlow, J. Wang, J. W. Perry, S. R. Marder, Adv. Polym. Sci. 2008, 213, 1-95
6. H. M. Kim, B. R. Cho, Acc. Chem. Res. 2009, 42, 863-872
7. F. Terenziani, C. Katan, E. Badaeva, S. Tretiak, M. Blanchard-Desce, Adv. Mater. 2008, 20, 4641-4678
8. M. Albota, D. Beljonne, J.-L. Brédas, J. E. Ehrlich, J.-Y. Fu, A. A. Heikal, S. E. Hess, T. Kogej, M. D. Levin, S. R. Marder, D. McCord-Maughon, J. W. Perry, H. Röckel, M. Rumi, G. Subramaniam, W. W. Webb, X.-L. Wu, C. Xu, Science 1998, 281, 1653-1656
9. B. A. Reinhardt, L. L. Brott, S. T. Clarson, A. G. Dillard, J. C. Bhatt, R. Kannan, L. Yuan, G. S. He, P. N. Prasad, Chem. Mater. 1998, 10, 1863-1874
10. J. Yoo, S. K. Yang, M.-Y. Jeong, H. C. Ahn, S.-J. Jeon, B. R. Cho, Org. Lett. 2003, 5, 645-648
11. X. Dong, J. H. Han, C. H. Heo, H. M. Kim, Z. Liu, B. R. Cho, Anal. Chem. 2012, 84, 8110-8113.
12. H. M. Kim, B. R. Cho, Chem. Commun. 2009, 153-164
13. G. S. He, L.-S. Tan, Q. Zheng, P. N. Prasad, Chem. Rev. 2008, 108, 1245-1330.
14. A. E. Tschitschibabin, Ber. Dtsch. Chem. Ges. A 1924, 57, 2092-2101.
15. A. Elhakmaoui, A. Gueiffier, J.-C. Milhavet, Y. Blache, J.-P. Chapat, O. Chavignon, J.-C. Teulade, R. Snoeck, G. Andrei, E. De Clercq, Bioorg. Med. Chem. Lett. 1994, 4, 1937-1940
16. L. B. Townsend, J. C. Drach, WO9727205; [Chem. Abstr. 1997, 127, 190983j]
17. S. Mavel, J. L. Renou, C. Galtier, R. Snoeck, G. Andrei, J. Balzarini, E. De Clercq, A. Gueiffier, Arzneim.-Forsch. 2001, 51, 304; [Chem. Abstr. 2001, 135, 131730s].
18. R. B. Lacerda, C. K. de Lima, L. L. da Silva, N. C. Romeiro, A. L. P. Miranda, E. J. Barreiro, C. A. M. Fraga, Bioorg. Med. Chem. 2009, 17, 74-84
19. E. Abignente, Actual. Chim. Ther. 1991, 18, 193-214; [Chem. Abstr. 1991, 115, 256028n].
20. E. Abignente, F. Arena, E. Luraschi, C. Saturnino, F. Rossi, E. Lampa, M. Cazzola, E. Brandinelli, R. Marrazzo, E. Marmo, Rend. Atti Accad. Sci. Med. Chir. 1985, 139, 313; [Chem. Abstr. 1986, 105, 126822z]
21. L. Almirante, L. Polo, A. Mugnaini, E. Provinciali, P. Rugarli, A. Biancotti, A. Gamba, W. Murmann, J. Med. Chem. 1965, 8, 305-312.
22. J. C. Teulade, G. Grassy, J. P. Girard, J. P. Chapat, Eur. J. Med. Chem. 1978, 13, 271-276.
23. K. F. Byth, J. D. Culshaw, S. Green, S. Oakes, A. P. Thomaset, Bioorg. Med. Chem. Lett. 2004, 14, 2245-2248.
24. S. Z. Langer, S. Arbilla, J. Benavides, Adv. Biochem. Psychopharmacol. 1990, 46, 61-72.
25. T. Swainston Harrison, G. M. Keating, CNS Drugs 2005, 19, 65-89.
26. T. Ueda, K. Mizusgige, K. Yukiiri, T. Takahashi, M. Kohno, Cerebrovasc. Dis. 2003, 16, 396-403.
27. F. Shibahara, E. Yamaguchi, A. Kitagawa, A. Imai, T. Murai, Tetrahedron 2009, 65, 5062-5073.
28. E. Yamaguchi, F. Shibahara, T. Murai, J. Org. Chem. 2011, 76, 6146-6158
29. F. Shibahara, R. Sugiura, E. Yamaguchi, A. Kitagawa, T. Murai, J. Org. Chem. 2009, 74, 3566-3568
30. F. Shibahara, Y. Dohke, T. Murai, J. Org. Chem. 2012, 77, 5381-5388
31. Y. Shigemitsu, T. Mutai, H. Houjou, K. Araki, J. Phys. Chem. A 2012, 116, 12041-12048.
32. H. Tomoda, T. Hirano, S. Saito, T. Mutai, K. Araki, Bull. Chem. Soc. Jpn. 1999, 72, 1327-1334.
33. A. Douhal, F. Amatguerri, A. U. Acuña, J. Phys. Chem. 1995, 99, 76-80.
34. T. Mutai, H. Tomoda, T. Ohkawa, Y. Yabe, K. Araki, Angew. Chem. 2008, 120, 9664-9666
35. Angew. Chem. Int. Ed. 2008, 47, 9522-9524
36. H. Shono, T. Ohkava, H. Tomoda, T. Mutai, K. Araki, ACS Appl. Mater. Interfaces 2011, 3, 654-657.
37. A. J. Stasyuk, M. Banasiewicz, M. K. Cyrański, D. T. Gryko, J. Org. Chem. 2012, 77, 5552-5558.
38. J. Catalan, E. Mena, F. Fabero, F. Amat-Guerri, J. Chem. Phys. 1992, 96, 2005-2016.
39. M. Aginagalde, Y. Vara, A. Arrieta, R. Zangi, V. L. Cebolla, A. Delgado-Camõn, F. P. Cossío, J. Org. Chem. 2010, 75, 2776-2784
40. O. N. Burchak, L. Mugherli, M. Ostuni, J. J. Lacapère, M. Y. Balakirev, J. Am. Chem. Soc. 2011, 133, 10058-10061.
41. A. Gueiffier, M. Lhassani, A. Elhakmaoui, R. Snoeck, G. Andrei, O. Chavignon, J.-C. Teulade, A. Kerbal, E. M. Essassi, J.-C. Debouzy, M. Witvrouw, Y. Blache, J. Balzarini, E. De Clercq, J.-P. Chapat, J. Med. Chem. 1996, 39, 2856-2859
42. A. Gueiffier, S. Mavel, M. Lhassani, A. Elhakmaoui, R. Snoeck, G. Andrei, O. Chavignon, J.-C. Teulade, M. Witvrouw, J. Balzarini, E. De Clercq, J.-P. Chapat, J. Med. Chem. 1998, 41, 5108-5112
43. E. S. Hand, W. W. Paudler, J. Org. Chem. 1978, 43, 2900-2906.
44. E. F. DiMauro, J. M. Kennedy, J. Org. Chem. 2007, 72, 1013-1016
45. K. Groebke, L. Weber, F. Mehlin, Synlett 1998, 661-663
46. M. Adib, E. Sheikhi, N. Rezaei, Tetrahedron Lett. 2011, 52, 3191-3194.
47. N. Shao, G.-X. Pang, C.-X. Yan, G.-F. Shi, Y. Cheng, J. Org. Chem. 2011, 76, 7458-7465.
48. A. R. Katritzky, Y.-J. Xu, H. Tu, J. Org. Chem. 2003, 68, 4935-4937.
49. H.-J. Knölker, R. Hitzemann, R. Boese, Chem. Ber. 1990, 123, 327-339.
50. A. S. Kiselyov, Tetrahedron Lett. 2006, 47, 2941-2944.
51. A. J. Hubert, H. Reimlinger, Chem. Ber. 1970, 103, 3811-3816.
52. R.-L. Yan, H. Yan, C. Ma, Z.-Y. Ren, X.-A. Gao, G.-S. Huang, Y.-M. Liang, J. Org. Chem. 2012, 77, 2024-2028
53. H. Cao, H. Zhan, Y. Lin, X. Lin, Z. Du, H. Jiang, Org. Lett. 2012, 14, 1688-1691.
54. N. Chernyak, V. Gevorgyan, Angew. Chem. 2010, 122, 2803-2806
55. Angew. Chem. Int. Ed. 2010, 49, 2743-2746.
56. S. Mishra, R. Ghosh, Synthesis 2011, 3463-3470.
57. S. K. Guchhait, A. L. Chandgude, G. Priyadarshani, J. Org. Chem. 2012, 77, 4438-4444.
58. P. Liu, L.-S. Fang, X. Lei, G.-Q. Lin, Tetrahedron Lett. 2010, 51, 4605-4608.
59. B. V. S. Reddy, P. S. Reddy, Y. J. Reddy, J. S. Yadav, Tetrahedron Lett. 2011, 52, 5789-5793.
60. R. J. Sundberg, J. Daniel, D. J. Dahlhausen, G. Manikumar, B. Mavunkel, A. Biswas, V. Srinivasan, H. A. Musallam, W. A. Reid, Jr., A. L. Ager, J. Med. Chem. 1990, 33, 298-307.
61. V. S. C. Yeh, P. E. Wiedeman, Tetrahedron Lett. 2006, 47, 6011-6016.
62. A. Douhal, F. Amat-Guerri, A. U. Acuña, Angew. Chem. 1997, 109, 1586-1588
63. Angew. Chem. Int. Ed. Engl. 1997, 36, 1514-1516.
64. Y. Y. Zhao, M. R. Wasielewski, Tetrahedron Lett. 1999, 40, 7047-7050
65. X.-F. Zhang, J. Wang, J. Phys. Chem. A 2011, 115, 8597-8603.
66. K. Skonieczny, A. I. Ciuciu, E. Nichols, V. Hugues, M. Blanchard-Desce, L. Flamigni, D. T. Gryko, J. Mater. Chem. 2012, 22, 20649-20664
67. A. I. Ciuciu, K. Skonieczny, D. Koszelewski, D. T. Gryko, L. Flamigni, J. Phys. Chem. C 2013, 117, 7 91-803.
68. M. Barzoukas, M. Blanchard-Desce, J. Chem. Phys. 2000, 113, 3951-3959.
69. O. Mongin, L. Porrès, M. Charlot, C. Katan, M. Blanchard-Desce, Chem. Eur. J. 2007, 13, 1481-1498.
70. L. Ventelon, S. Charier, L. Moreaux, J. Mertz, M. Blanchard-Desce, Angew. Chem. 2001, 113, 2156-2159
71. Angew. Chem. Int. Ed. 2001, 40, 2098-2101.
72. A. Mangalum, R. J. Gilliard, Jr., J. M. Hanley, A. M. Parker, R. C. Smith, Org. Biomol. Chem. 2010, 8, 5620-5627.
73. J. H. Li, Y. Liang, Y. X. Xie, J. Org. Chem. 2005, 70, 4393-4396.
74. L. Flamigni, A. M. Talarico, S. Serroni, F. Puntoriero, M. J. Gunter, M. R. Johnston, T. P. Jeynes, Chem. Eur. J. 2003, 9, 2649-2659.
75. C. Xu, W. W. Webb, J. Opt. Soc. Am. B 1996, 13, 481-491
76. M. H. V. Werts, N. Nerambourg, D. Pélégry, Y. Le Grand, M. Blanchard-Desce, Photochem. Photobiol. Sci. 2005, 4, 531-538.