Photophysical, crystallographic, and electrochemical characterization of novel conjugated thiopheno azomethines

Journal of Materials Chemistry

Volumn 17, Issue 10, 2007, Pages 972-979

  Bourgeaux, Marie ^a   Guarìn, Sergio Andrés Pérez ^a   Skene, W G ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CRYSTALLOGRAPHY; ELECTROCHEMISTRY; ELECTRON ENERGY LEVELS; ISOMERS; OXIDATION; THERMODYNAMICS;

ELECTROCHEMICAL OXIDATION; INTERNAL CONVERSION; RADICAL CATION; THIOPHENO AZOMETHINES;

AMINES;

EID: 33847362694     PISSN: 09599428     EISSN: 13645501     Source Type: Journal    
DOI: 10.1039/b615325a     Document Type: Article

References (66)

1. A. G. MacDiarmid Angew. Chem., Int. Ed., 2001, 40, 2581-2590
2. C. D. Dimitrakopoulos, P. R. L. Malenfant Adv. Mater., 2002, 14, 99-117
3. L. Rupprecht, Conductive Polymers and Plastics in Industrial Applications, Society of Plastics Engineers/Plastics Design Library, Brookfield, CT, 1999
4. I. F. Perepichka, D. F. Perepichka, H. Meng, F. Wudl Adv. Mater., 2005, 17, 2281-2305
5. M. Leclerc J. Polym. Sci., Part A: Polym. Chem., 2001, 17, 2867-2873
6. C. Wang, S. Shieh, E. LeGoff, M. G. Kanatzidis Macromolecules, 1996, 29, 3147-3156
7. C.-J. Yang, S. A. Jenekhe Chem. Mater., 1991, 3, 878-887
8. N. Kiriy, V. Bocharova, A. Kiriy, M. Stamm, F. C. Krebs, H.-J. Adler Chem. Mater., 2004, 16, 4765-4771
9. F.-C. Tsai, C.-C. Chang, C.-L. Liu, W.-C. Chen, S. A. Jenekhe Macromolecules, 2005, 38, 1958-1966
10. C.-J. Yang, S. A. Jenekhe Macromolecules, 1995, 28, 1180-1196
11. F. Wudl, E. T. Zellers J. Am. Chem. Soc., 1980, 102, 4283-4284
12. V. K. Gewald, M. Kleinert, B. Thiele, M. Hentschel J. Prakt. Chem., 1972, 314, 303-314
13. W. G. Skene, World Pat. WO 2005073265, 2005
14. J. Seixas de Melo, F. Elisei, C. Gartner, G. G. Aloisi, R. S. Becker J. Phys. Chem. A, 2000, 104, 6907-6911
15. L. J. Andrews, A. Deroulede, H. Linschltz J. Phys. Chem., 1978, 82, 2304-2309
16. P. Frère, J.-M. Raimundo, P. Blanchard, J. Delaunay, P. Richomme, J.-L. Sauvajol, J. Orduna, J. Garin, J. Roncali J. Org. Chem., 2003, 68, 7254-7265
17. I. Jestin, P. Frère, N. Mercier, E. Levillain, D. Stievenard, J. Roncali J. Am. Chem. Soc., 1998, 120, 8150-8158
18. E. H. Elandaloussi, P. Frère, P. Richomme, J. Orduna, J. Garin, J. Roncali J. Am. Chem. Soc., 1997, 119, 10774-10784
19. T. Geisler, J. C. Petersen, T. Bjornholm, E. Fischer, J. Larsen, C. Dehu, J.-L. Bredas, G. V. Tormos, P. N. Nugara J. Phys. Chem., 1994, 98, 10102-10111
20. G. Ginocchietti, G. Galiazzo, U. Mazzucato, A. Spalletti Photochem. Photobiol. Sci., 2005, 4, 547-553
21. F. C. Grozema, P. T. Van Duijnen, L. D. A. Siebbeles, A. Goossens, S. W. De Leeuw J. Phys. Chem. B, 2004, 108, 16139-16146
22. J. Seixas de Melo, F. Elisei, R. S. Becker J. Chem. Phys., 2002, 117, 4428-4435
23. D. Wasserberg, P. Marsal, S. C. J. Meskers, R. A. J. Janssen, D. Beljonne J. Phys. Chem. B, 2005, 109, 4410-4415
24. Handbook of Conducting Polymers, ed. T. A. Skotheim, Marcel Dekker, Inc., New York, 1986
25. N. J. Turro, Modern Molecular Photochemistry, University Science Books, Sausalito, CA, 1991
26. M. W. C. Dharma-Wardana, M. Z. Zgierski J. Opt. A: Pure Appl. Opt., 2002, 4, S278-S281
27. D. Wasserberg, S. P. Dudek, S. C. J. Meskers, R. A. J. Janssen Chem. Phys. Lett., 2005, 411, 273-277
28. J. Seixas de Melo, H. D. Burrows, M. Svensson, M. R. Andersson, A. P. Monkman J. Chem. Phys., 2003, 118, 1550-1556
29. R. S. Becker, J. Seixas de Melo, A. L. Maçanita, F. Elisei J. Phys. Chem., 1996, 100, 18683-18695
30. V. Wintgens, P. Valat, F. Garnier J. Chem. Phys., 1994, 98, 228-232
31. I. Carmichael, and G. L. Hug, in Handbook of Organic Photochemistry, ed. J. C. Scaiano, CRC Press, Boca Raton, FL, 1989, pp. 369-403
32. I. Carmichael, W. P. Helman, G. L. Hug J. Phys. Chem. Ref. Data, 1987, 16, 239-260
33. I. Carmichael, G. L. Hug J. Phys. Chem. Ref. Data, 1986, 15, 1-250
34. M. Amati, C. Bonini, M. D’Auria, M. Funicello, F. Lelj, R. Racioppi J. Org. Chem., 2006, 71, 7165-7179
35. J.-M. Lehn Chem.-Eur. J., 2006, 12, 5910-5915
36. W. G. Skene, S. A. Perez Guarin J. Fluoresc., 2006, submitted
37. G. Tourillon, in Handbook of Conducting Polymers, ed. T. A. Skotheim, Marcel Dekker, Inc., New York, 1986, pp. 293-350
38. G. Barbarella, M. Zambianchi, L. Antolini, U. Folli, F. Goldoni, D. Iarossi, L. Schenetti, A. Bongini J. Chem. Soc., Perkin Trans. 2, 1995, 1869-1873
39. G. Barbarella, M. Zambianchi, A. Bongini, L. Antolini Adv. Mater., 1994, 6, 561-564
40. W. G. Skene, S. Dufresne, T. Trefz, M. Simard Acta Crystallogr., Sect. E., 2006, 62, o2382-o2384
41. W. G. Skene, S. Dufresne Org. Lett., 2004, 6, 2949-2952
42. W. G. Skene, S. Dufresne Acta Crystallogr., Sect. E, 2006, 62, o1116-o1117
43. J. E. Kuder, H. W. Gibson, D. Wychick J. Org. Chem., 1975, 40, 875-879
44. G. Manecke, W. E. Wille, G. Kossmehl Makromol. Chem., 1972, 160, 111-126
45. H. B. Bürgi, J. D. Dunitz J. Chem. Soc. D, 1969, 472-473
46. C.-W. Wan, A. Burghart, J. Chen, F. Bergström, L. B.-Å. Johansson, M. F. Wolford, T. G. Kim, M. R. Topp, R. M. Hochstrasser, K. Burgess Chem.-Eur. J., 2003, 9, 4430-4441
47. G.-S. Jiao, L. H. Thoresen, K. Burgess J. Am. Chem. Soc., 2003, 125, 14668-14669
48. D. Zobel, G. Ruban Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst.Chem., 1978, 34, 1652-1657
49. Even though a suitable analogue for electrochemical data comparison should contain an electron withdrawing group similar to 3, no literature examples for derivatives of 5 are known
50. F. R. Diaz, M. A. del Valle, F. Brovelli, L. H. Tagle, J. C. Bernede J. Appl. Polym. Sci., 2003, 89, 1614-1621
51. X. B. Sun, Y. Q. Liu, S. Y. Chen, W. F. Qiu, G. Yu, Y. Q. Ma, T. Qi, H. J. Zhang, X. J. Xu, D. B. Zhu Adv. Funct. Mater., 2006, 16, 917-925
52. A. Yassar, J. Roncali, F. Garnier Macromolecules, 1989, 22, 804-809
53. P. T. Henderson, D. M. Collard Chem. Mater., 1996, 7, 1879-1889
54. The resulting oxidatively coupled products are not highly soluble in all organic solvents therefore only limited characterization is possible
55. The measured molecular weight was consistently obtained by electrochemical oxidation of 3 at +1.4 V for 10 minutes using the reported analytical conditions
56. J. Roncali Chem. Rev., 1992, 92, 711-738
57. 6 in anhydrous dichloromethane, glassy carbon working electron, Ag/AgCl (sat’d) reference electrode, silver-wire working and platinum auxiliary electrodes. Values are reported vs. SCE with ferrocene as an internal standard
58. C. Jérôme, C. Maertens, M. Mertens, R. Jérôme, C. Quattrocchi, R. Lazzaroni, J. L. Brédas Synth. Met., 1996, 83, 103-109
59. C. Jérôme, C. Maertens, M. Mertens, R. Jérôme, C. Quattrocchi, R. Lazzaroni, J. L. Brédas Synth. Met., 1997, 84, 163-164
60. Y. Wei, C. C. Chan, J. Tian, G. W. Jang, K. F. Hsueh Chem. Mater., 1991, 3, 888-897
61. K. Meerholz, J. Heinze Electrochim. Acta, 1996, 41, 1839-1854
62. P. Frère, J.-M. Raimundo, P. Blanchard, J. Delaunay, P. Richomme, J.-L. Sauvajol, J. Orduna, J. Garin, J. Roncali J. Org. Chem., 2003, 68, 7254-7265
63. J. Seixas de Melo, H. D. Burrows, M. Svensson, M. R. Andersson, A. P. Monkman J. Chem. Phys., 2003, 118, 1550-1556
64. J. Seixas de Melo, L. M. Silva, L. G. Arnaut, R. S. Becker J. Chem. Phys., 1999, 111, 5427-5433
65. J. C. Scaiano, CRC Handbook of Organic Photochemistry, CRC Press, Boca Raton, FL, 1989
66. R. S. Murphy, C. P. Moorlag, W. H. Green, C. Bohne J. Photochem. Photobiol., A, 1997, 110, 123-129