Reaction of amines with 8-methylthioBODIPY: Dramatic optical and laser response to amine substitution

Chemistry - An Asian Journal

Volumn 8, Issue 11, 2013, Pages 2691-2700

  Esnal, Ixone ^a   Urías Benavides, Arlette ^b   Gõmez Durán, C F Azael ^b   Osorio Martínez, Carlos A ^b   García Moreno, Inmaculada ^c   Costela, Angel ^c   Bañuelos, Jorge ^a   Epelde, Nerea ^a   Lõpez Arbeloa, Iñigo ^a   Hu, Rongrong ^d   Tang, Ben Zhong ^d   Peña Cabrera, Eduardo ^b  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

^b UNIVERSITY OF GUANAJUATO   (Mexico)

^c INSTITUTO DE QUÍMICA FÍSICA ROCASOLANO   (Spain)

^d HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

Author keywords

charge transfer; dyes pigments; fluorescence; heterocycles; laser chemistry

Indexed keywords

BLUE FLUORESCENCE; BORON DIPYRROMETHENE; DYES/PIGMENTS; FLUORESCENT PRODUCTS; HETEROCYCLES; INTRAMOLECULAR CHARGE TRANSFERS; LASING PERFORMANCE; STERIC HINDRANCES;

CHARGE TRANSFER; CHEMICAL REACTIONS; FLUORESCENCE; LASER CHEMISTRY; QUENCHING; SOLVENTS;

AMINES;

EID: 84887021403     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.201300760     Document Type: Article

References (61)

1. R. Ziessel, G. Ulrich, A. Harriman, New J. Chem. 2007, 31, 496-501
2. G. Ulrich, R. Ziessel, A. Harriman, Angew. Chem. 2008, 120, 1202-1219
3. Angew. Chem. Int. Ed. 2008, 47, 1184-1201
4. A. C. Benniston, G. Copley, Phys. Chem. Chem. Phys. 2009, 11, 4124-4131
5. A. Loudet, K. Burgess, Chem. Rev. 2007, 107, 4891-4932
6. T. E. Wood, A. Thompson, Chem. Rev. 2007, 107, 1831-1861.
7. R. West, C. Panagabko, J. Atkinson, J. Org. Chem. 2010, 75, 2883-2892
8. T. Ehrenschwender, H.-A. Wagenknecht, Synthesis 2008, 3657-3662
9. Y. Rio, W. Seitz, A. Gouloumis, P. Vazquez, J. L. Sessler, D. M. Guldi, T. Torres, Chem. Eur. J. 2010, 16, 1929-1940
10. M. Koepf, A. Trabolsi, M. Elhabiri, J. A. Wytko, D. Paul, A. M. Albrecht-Gary, J. Weiss, Org. Lett. 2005, 7, 1279-1282
11. C. Y. Lee, J. T. Hupp, Langmuir 2010, 26, 3760-3765
12. M. R. Rao, S. M. Mobin, M. Ravikanth, Tetrahedron 2010, 66, 1728-1734
13. M. Vendrell, G. G. Krishna, K. K. Ghosh, D. Zhai, J.-S. Lee, Q. Zhu, Y. H. Yau, S. G. Shochat, H. Kim, J. Chunge, Y.-T. Chang, Chem. Commun. 2011, 47, 8424-8426
14. N. Boens, W. Qin, M. Baruah, W. M. De Borggraeve, A. Filarowski, N. Smisdom, M. Ameloot, L. Crovetto, E. M. Talavera, J. M. Alvarez-Pez, Chem. Eur. J. 2011, 17, 10924-10934
15. N. Boens, V. Leen, W. Dehaen, Chem. Soc. Rev. 2012, 41, 1130-1172
16. T. Cheng, T. Wang, W. Zhu, Y. Yang, B. Zeng, Y. Xu, Chem. Commun. 2011, 47, 3915-3917
17. J. Godoy, G. Vives, J. M. Tour, Org. Lett. 2010, 12, 1464-1467
18. J. Lu, H. Fu, Y. Zhang, Z. J. Jakubek, Y. Tao, S. Wang, Angew. Chem. 2011, 123, 11862-11866
19. Angew. Chem. Int. Ed. 2011, 50, 11658-11662
20. J. G. Baker, L. A. Adams, K. Salchow, S. N. Mistry, R. J. Middleton, S. J. Hill, B. J. Kellam, Med. Chem. 2011, 54, 6874-3887
21. T. Bura, N. Leclerc, S. Fall, P. Léveque, T. Heiser, R. Ziessel, Org. Lett. 2011, 13, 6030-6033
22. D. R. Kim, H.-C. Ahn, W.-J. Lee, D.-R. Ahn, Chem. Commun. 2011, 47, 791-793
23. A. P. Singh, K. M. Lee, D. P. Murale, T. Jun, H. Liew, Y.-H. Suh, D. G. Churchill, Chem. Commun. 2012, 48, 7298-7300
24. R. Wang, F. Yu, P. Liu, L. Chen, Chem. Commun. 2012, 48, 5310-5312
25. N. Sakamoto, C. Ikeda, M. Yamamura, T. Nabeshima, Chem. Commun. 2012, 48, 4818-4820.
26. R. W. Wagner, J. S. Lindsey, Pure Appl. Chem. 1996, 68, 1373-1380.
27. T. V. Goud, A. Tutar, J.-F. Biellmann, Tetrahedron 2006, 62, 5084-5091.
28. H. Prokopcová, C. O. Kappe, Angew. Chem. 2008, 120, 3732-3734
29. Angew. Chem. Int. Ed. 2008, 47, 3674-3676
30. H. Prokopcová, C. O. Kappe, Angew. Chem. 2009, 121, 2312-2322
31. Angew. Chem. Int. Ed. 2009, 48, 2276-2286.
32. E. Peña-Cabrera, A. Aguilar-Aguilar, M. González- Domínguez, E. Lager, R. Zamudio-Vázquez, J. Godoy-Vargas, F. Villanueva, Org. Lett. 2007, 9, 3985-3988
33. I. J. Arroyo, R. Hu, G. Merino, B. Z. Tang, E. Peña-Cabrera, J. Org. Chem. 2009, 74, 5719-5722
34. E. Lager, J. Liu, A. Aguilar-Aguilar, B. Z. Tang, E. Peña-Cabrera, J. Org. Chem. 2009, 74, 2053-2058
35. I. J. Arroyo, R. Hu, B. Z. Tang, F. I. Lõpez, E. Peña-Cabrera, Tetrahedron 2011, 67, 7244-7250
36. J. Bañuelos, I. J. Arroyo-Cõrdoba, I. Valois-Escamilla, A. Alvarez-Hernández, E. Peña-Cabrera, R. Hu, B. Z. Tang, I. Esnal, V. Martínez, I. Lõpez Arbeloa, RSC Adv. 2011, 1, 677-684.
37. C. F. A. Gõmez-Durán, I. García-Moreno, A. Costela, V. Martin, R. Sastre, J. Bañuelos, F. Lõpez Arbeloa, I. Lõpez Arbeloa, E. Peña-Cabrera, Chem. Commun. 2010, 46, 5103-5105
38. J. Bañuelos, V. Martín, C. F. A. Gõmez-Durán, I. J. Arroyo-Cõrdoba, E. Peña-Cabrera, I. García-Moreno, A. Costela, M. E. Pérez-Ojeda, T. Arbeloa, I. Lõpez Arbeloa, Chem. Eur. J. 2011, 17, 7261-7270
39. C. A. Osorio-Martínez, A. Urías-Benavides, C. F. A. Gõmez-Durán, J. Bañuelos, I. Esnal, I. Lõpez Arbeloa, E. Peña-Cabrera, J. Org. Chem. 2012, 77, 5434-5438
40. R. I. Roacho, A. Metta-Magaña, M. M. Portillo, E. Peña-Cabrera, K. H. Pannell, J. Org. Chem. 2013, 78, 4245-4250.
41. J. M. Murphy, C. C. Tzschucke, J. F. Hartwig, Org. Lett. 2007, 9, 757-760.
42. Laser Dyes, 3rd ed. (Ed.: U. Brackmann), Lambda Physik AG, Göttingen, 2000
43. Molecular Fluorescence: Principles and Applications (Ed.:, B. Valeur,), Wiley-VCH, Weiheim, 2002
44. A. N. Fletcher, M. E. Pietrak, Appl. Phys. B 1985, 37, 151-157
45. S. Nad, M. Kumbhakar, H. Pal, J. Phys. Chem. A 2003, 107, 4808-4816
46. J. N. Moorthy, P. Natarajan, P. Venkatakrishnan, D.-F. Huang, T. J. Chow, Org. Lett. 2007, 9, 5215-5218
47. Q.-X. Tong, S.-L. Lai, M.-Y. Chan, Y.-C. Zhou, H.-L. Kwong, C.-S. Lee, S.-T. Lee, Chem. Mater. 2008, 20, 6310-6312
48. A. Lida, S. Yamaguchi, Chem. Commun. 2009, 3002-3004
49. R. M. Adhikari, D. C. Neckers, B. K. Shah, J. Org. Chem. 2009, 74, 3341-3349.
50. A. C. Benniston, S. Clift, J. Hagon, H. Lemmetyinen, N. V. Tkachenko, W. Clegg, R. W. Harrington, ChemPhysChem 2012, 13, 3672-3681.
51. L. Xu, K. Burgess, J. Org. Chem. 2008, 73, 8711-8718
52. A. Saha, A. Samanta, J. Phys. Chem. A 2002, 106, 4763-4771
53. B. Bhattacharya, A. Samanta, Chem. Phys. Lett. 2007, 442, 316-321
54. K. A. Zachariasse, M. Grobys, T. von der Haar, A. Hebecker, Y. V. Illichev, O. Morawski, I. Rückert, W. Kühnle, J. Photochem. Photobiol. A 1997, 105, 373-383.
55. J. W. Verhoeven, Pure Appl. Chem. 1990, 62, 1585-1596
56. J. W. Verhoeven, T. Scherer, R. J. Willemse, Pure Appl. Chem. 1993, 65, 1717-1722.
57. A. C. Benniston, A. Harriman, V. L. Whittle, M. Zelzer, R. W. Harrington, W. Clegg, Photochem. Photobiol. Sci. 2010, 9, 1009-1017
58. A. C. Benniston, G. Copley, H. Lemmetyinen, N. V. Tkachenko, ChemPhysChem 2010, 11, 1685-1692
59. S. Mula, K. Elliot, A. Harriman, R. Ziessel, J. Phys. Chem. A 2010, 114, 10515-10522.
60. M. Kollmannsberger, K. Rurack, U. Resch-Genger, J. Daub, J. Phys. Chem. A 1998, 102, 10211-10220.
61. J. C. de Mello, H. F. Wittmann, R. H. Friend, Adv. Mater. 1997, 9, 230-232.