Photophysical, crystallographic, and electrochemical characterization of symmetric and unsymmetric self-assembled conjugated thiopheno azomethines

Journal of Organic Chemistry

Volumn 72, Issue 7, 2007, Pages 2631-2643

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

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; ALDEHYDES; AROMATIC COMPOUNDS; CHARACTERIZATION; CONDENSATION; CONJUGATED POLYMERS; ELECTROCHEMISTRY; HYDROLYSIS; ISOMERS; SYNTHESIS (CHEMICAL);

ALDEHYDE ADDITION; CONJUGATED AZOMETHINES; HYDROLYTICALLY RESISTANT;

CRYSTALLOGRAPHY;

ALDEHYDE DERIVATIVE; AZOMETHINE YLIDE; CATION; NITROGEN; RADICAL; REAGENT; SOLVENT; THIOPHENE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; COVALENT BOND; CROSS COUPLING REACTION; CRYSTALLOGRAPHY; DEVICE; ELECTROCHEMICAL ANALYSIS; ENERGY; FLUORESCENCE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; ISOMER; OXIDATION; PHOSPHORESCENCE; PHOTOPHYSICS; PHYSICS; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEADY STATE; STOICHIOMETRY; STRUCTURE ANALYSIS; SYNTHESIS; TEMPERATURE DEPENDENCE; THERMODYNAMICS; TIME;

EID: 34047202256     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070100o     Document Type: Article

References (93)

1. (a) MacDiarmid, A. G. Angew. Chem., Int. Ed. 2001, 40, 2581-2590.
2. (b) Dimitrakopoulos, C. D.; Malenfant, P. R. L. Adv. Mater. 2002, 14, 99-117.
3. (c) Holliday, B. J.; Swager, T. M. Chem. Commun. 2005, 23-36.
4. (a) Rupprecht, L. Conductive Polymers and Plastics in Industrial Applications; Society of Plastics Engineers/Plastics Design Library: Brookfield, CT, 1999.
5. (b) Brabec, C. J.; Sariciftci, N. S.; Hummelen, J. C. Adv. Funct. Mater. 2001, 11, 15-26.
6. Katz, H. E.; Dodabalapur, A.; Bao. Z. In Handbook of Oligo- and Polythiophenes; Fichou, D., Ed.; Wiley-VCH Verlag GmbH: Weinheim, Germany, 1999; pp 459-489.
7. Jenekhe, S. A. Chem. Mater. 2004, 16, 4381-4382.
8. Lavastre, O.; Ilitchev, I. I.: Jegou, G.: Dixneuf, P. H. J. Am. Chem. Soc. 2002, 124, 5278-5279.
9. (a) Kraft, A.; Grimsdale, A. C.; Holmes, A. B. Angew. Chem., Int. Ed. 1998, 37, 402-428.
10. (b) Leclerc, M. J. Polym. Sci., Part A: Polym. Chem. 2001, 17, 2867-2873.
11. (a) Wang, C.; Shieh, S.; LeGoff, E.; Kanatzidis, M. G. Macromolecules 1996, 29, 3147-3156.
12. (b) Yang, C-J.; Jenekhe, S. A. Chem. Mater. 1991, 3, 878-887.
13. Thomas, O.; Inganäs. O.; Andersson, M. R. Macromolecules 1998, 31, 2676-2678.
14. (a) Kucybala, Z.; Pyszka, I.; Marciniak, B.: Hug, G. L.; Paczkowski, J. J. Chem. Soc., Perkin Trans. 2 1999, 2147-2154.
15. (b) Skopalová, J.; Lemr, K.; Kotouèek, M.; Èâp, L.; Barták, P. Fresenius J. Anal. Chem. 2001, 370, 963-969.
16. (a) Suematsu, K.; Nakamura, K.; Takeda, J. Colloid Polym. Sci. 1983, 261, 493-501.
17. (b) Morgan, P. W.; Kwolek, S. L.; Pletcher, T. C. Macromolecules 1987, 20, 729-739.
18. Gewald, V. K.: Kleinen, M.; Thiele, B.; Hentschel, M. J. Prakt. Chem. 1972, 314, 303-314.
19. (a) Tsai, F.-C.; Chang, C.-C.; Liu, C.-L.; Chen, W.-C.; Jenekhe, S. A. Macromolecules 2005, 38, 1958-1966.
20. (b) Kiriy, N.; Bocharova, V.; Kiriy, A.; Stamm, M.; Krebs, F. C.; Adler, H.-J. Chem. Mater. 2004, 16, 4765-4771.
21. Skene, W. G. WO 2005073265. 2005.
22. (a) Skene, W. G.; Dufresne, S. Org. Lett. 2004, 6, 2949-2952.
23. (b) Bourgeaux, M.; Pérez Guarìn, S. A.; Skene, W. G. J. Mater. Chem. 2007, 17, 972-979.
24. (c) Dufresne, S.; Bourgeaux, M.; Skene, W. G. J. Mater. Chem. 2007, 10.1039/b616379c.
25. Bourgeaux. M.; Skene, W. G. Macromolecules 2007, 40, 1792-1795.
26. Becker, R. S.; Seixas de Melo, J.; Maçanita, A. L.; Elisei, F. J. Phys. Chem. 1996, 100, 18683-18695.
27. Seixas de Melo, J.; Elisei, F.; Becker, R. S. J. Chem. Phys. 2002, 117, 4428-4435.
28. Seixas de Melo, J.; Burrows, H. D.; Svensson, M.; Andersson, M. R.; Monkman, A. P. J. Chem. Phys. 2003, 118, 1550-1556.
29. Seixas de Melo, J.; Suva, L. M.; Arnaut, L. G.; Becker, R. S. J. Chem. Phys. 1999, 111, 5427-5433.
30. Seixas de Melo, J.; Elisei, F.; Gartner. C.; Aloisi, G. G.; Becker, R. S. J. Phys. Chem. A 2000, 104, 6907-6911.
31. Scaiano, J. C. CRC Handbook of Organic Photochemistry; CRC Press: Boca Raton, FL, 1989.
32. Carmichael, I.; Hug, G. L. J. Phys. Chem. Ref. Data 1986, 15, 1-250.
33. (a) Andrews, L. J.; Deroulede. A.; Linschltz, H. J. Phys. Chem. 1978, 82, 2304-2309.
34. (b) Murphy, R. S.; Moorlag. C. P.; Green, W. H.; Bohne, C. J. Photochem. Photobiol, A 1997, 110, 123-129.
35. Connelly, N. G.; Geiger, W. E. Chem. Rev. 1996, 96, 877-910.
36. Skene, W. G. Polym. Prepr. 2004, 45, 252-253.
37. Skene, W. G.; Dufresne, S.; Trefz, T.; Simard, M. Acta Crystallogr. 2006, E62, o2382-o2384.
38. (a) Skene, W. G. PCT Int. Appl., 2005.
39. (b) Bourgeaux, M.; Vomsheid, S.; Skene, W. G. Synth. Commun. 2007, in press.
40. Skene, W. G.; Trefz, T. PMSE Prepr. 2004, 91, 326-327.
41. Horowitz, G. Adv. Mater. 1998, 10, 365-377.
42. Van Der Looy, J. F. A.; Thys, G. J. H.; Dieltiens, P. E. M.; De Schrijver, D.; Van Alsenoy, C.; Geise, H. J. Tetrahedron 1997, 53, 15069-15084.
43. Wasserberg, D.; Marsal, P.; Meskers, S. C. J.; Janssen, R. A. J.; Beljonne, D. J. Phys. Chem. B 2005, 109, 4410-4415.
44. Wasserberg, D.; Dudek, S. P.; Meskers, S. C. J.; Janssen, R. A. J. Chem. Phys. Lett. 2005, 411, 273-277.
45. Wintgens, V.: Valat, P.; Garnier, F. J. Chem. Phys. 1994, 98, 228-232.
46. Scaiano, J. C.; Lissi, E. A.; Stewart, L. C. J. Am. Chem. Soc. 1984, 106, 1539-1542.
47. (a) Scaiano, J. C.; Redmond, R. W.; Mehta, B.; Arnason, J. T. Photochem. Photobiol. 1990, 52, 655-659.
48. (b) Reyftmann, J. P.; Kagan, J.; Santus, R.; Morliere, P. Photochem. Photobiol. 1985, 41, 1-7.
49. (a) Amati, M.; Bonini, C.; D'Auria, M.; Funicello, M.; Lelj, F.; Racioppi, R. J. Org. Chem. 2006, 71, 7165-7179.
50. (b) Lehn, J.-M. Chem.-Eur. J. 2006, 12, 5910-5915.
51. (a) Lygaitis, R.; Grazulevicius, J.; Van, F. T.; Chevrot, C.; Jankauskas, V.; Jankunaite, D. J. Photochem. Photobiol, A 2006, 181, 67-72.
52. (b) Getautisa, V.; Grazulevicius, J. V.; Daskeviciene, M.; Malinauskas, T.; Gaidelis, V.; Jankauskas, V.; Tokarski, Z. J. Photochem. Photobiol., A 2006, 180, 23-27.
53. Diaz, F. R.; del Valle, M. A.; Brovelli, F.; Tagle, L. H.; Bernede, J. C. J. Appl. Polym. Sci. 2003, 89, 1614-1621.
54. (a) Yang, C.-J.; Jenekhe, S. A. Macromolecules 1995, 28, 1180-1196.
55. (b) Lund, H.; Hammerich, O. Organic Electrochemistry, 4th ed.; Marcel Dekker: New York, 2001.
56. (c) Caballero, A.; Tárraga, A.; Velasco, M. D.; Molina, P. Dalton Trans. 2006, 1390-1398.
57. (d) Catanescu, O.; Grigoras, M.; Colotin, G.; Dobreanu, A.; Hurduc, N.; Simionescu, C. I. Eur. Polym. J. 2001, 37, 2213-2216.
58. (e) Grigoras, M.; Catanescu, C. O.; Colotin, G. Macromol. Chem. Phys. 2001, 202, 2262-2266.
59. Higuchi, M.; Yamamoto, K. Polym. Adv. Technol. 2002, 13, 765-770.
60. (a) Zotti, G.; Randi, A.; Destri, S.; Porzio, W.; Schiavon, G. Chem. Mater. 2002, 14, 4550-4557.
61. (b) Brovelli, F.; Rivas, B. L.; Bernede, J. C. J. Chilean Chem. Soc. 2005, 50, 597-602.
62. Diaz, A. F.; Martinez, A.; Kanazawa, K. K.; Salmon, M. J. Electroanal. Chem. Interfacial Electrochem. 1981, 130, 181-187.
63. (a) Hansford, K. A.; Guarin, S. A. P.; Skene, W. G.; Lubell, W. D. J. Org. Chem. 2005, 70, 7996-8000.
64. (b) Haare, J. A. E. H. v.; Havinga, E. E.; Dongen, J. L. J. v.; Janssen, R. A. J.; Cornil, J.; Brédas, J.-L. Chem.-Eur. J. 1998, 4, 1509-1522.
65. (a) Jérôme, C.; Maertens, C.; Mertens, M.; Jérôme, R.; Quattrocchi, C.; Lazzaroni, R.; Brédas, J. L. Synth. Met. 1996, 83, 103-109.
66. (b) Jérôme, C.; Maertens, C.; Mertens, M.; Jérôme, R.; Quattrocchi, C.; Lazzaroni, R.; Brédas, J. L. Synth. Met. 1997, 84, 163-164.
67. (a) Sun, X. B.; Liu, Y. Q.; Chen, S. Y.; Qiu, W. F.; Yu, G.; Ma, Y. Q.; Qi, T.; Zhang, H. J.; Xu, X. J.; Zhu, D. B. Adv. Funct. Mater. 2006, 16, 917-925.
68. (b) Yassar, A.; Roncali, J.; Garnier, F. Macromolecules 1989, 22, 804-809.
69. (c) Henderson, P. T.; Collard, D. M. Chem. Mater. 1996, 7, 1879-1889.
70. Tourillon, G. In Handbook of Conducting Polymers; Skotheim, T. A., Ed.; Marcel Dekker, Inc.: New York, 1986; Vol. 1, pp 293-350.
71. Roncali, J. Chem. Rev. 1992, 92, 711-738.
72. Skene, W. G.; Dufresne, S. Acta Crystallogr. 2006, E62, o1116-01117.
73. (a) Kuder, J. E.; Gibson, H. W.; Wychick, D. J. Org. Chem. 1975, 40, 875-879.
74. (b) Manecke, G.; Wille, W. E.; Kossmehl, G. Makromol. Chem. 1972, 160, 111-126.
75. Bürgi, H. B.; Dunitz, J. D. Chem. Commun. 1969, 472-473.
76. Narasegowda, R. S.; Yathirajana, H. S.; Bolteb, M. Acta Crystallogr., Sect. E 2005, E61, o939-o940.
77. (a) Wan, C.-W.; Burghart, A.; Chen, J.; Bergström, F.; Johansson, L. B.-Å.; Wolford, M. F.; Kim, T. G.; Topp, M. R.; Hochstrasser, R. M.; Burgess, K. Chem.-Eur. J. 2003, 9, 4430-4441.
78. (b) Jiao, G.-S.: Thoresen, L. H.; Burgess, K. J. Am. Chem. Soc. 2003, 125, 14668-14669.
79. (a) Ruban, G.; Zobel, D. Acta Crystallogr., Sect. B 1975, B31, 2632-2634.
80. (b) Zobel, D.; Ruban, G. Acta Crystallogr., Sect. B 1978, B34, 1652-1657.
81. Blanchard, P.; Brisset, H.; Illien, B.; Riou, A.; Roncali, J. J. Org. Chem. 1997, 62, 2401-2408.
82. Pelletier, M.; Brisse, F.; Cloutier, R.; Leclerc, M. Acta Crystallogr., Sect. C 1995, C51, 1394-1397.
83. Roncali, J.; Thobie-Gautier, C. Adv. Mater. 1994, 6, 846-848.
84. Skene, W. G.; Trefz, T. Polym. Prepr. 2004, 45, 563-564.
85. (a) Frère, P.; Raimundo, J.-M.; Blanchard, P.; Delaunay, J.; Richomme, P.; Sauvajol, J.-L.; Orduna, J.; Garin, J.; Roncali, J. J. Org. Chem. 2003, 68, 7254-7265.
86. (b) Jestin, I.; Frère, P.; Mercier, N.; Levillain, E.; Stievenard, D.; Roncali. J. J. Am. Chem. Soc. 1998, 120, 8150-8158.
87. (c) Elandaloussi, E. H.; Frère, P.; Richomme, P.; Orduna, J.; Garin, J.; Roncali, J. J. Am. Chem. Soc. 1997, 119, 10774-10784.
88. (d) Geisler, T.; Petersen. J. C.: Bjornholm, T.; Fischer, E.; Larsen, J.: Dehu, C.; Bredas, J.-L.; Tormos, G. V.; Nugara, P. N. J Phys. Chem. 1994, 98, 10102-10111.
89. (a) Wei, Y.; Chan, C. C; Tian, J.; Jang, G. W.; Hsueh, K. F. Chem. Mater. 1991, 3, 888-897.
90. (b) Meerholz, K.; Heinze, J. Electrochim. Acta 1996, 41, 1839-1854.
91. (a) Audebert, P.; Catel, J.-M.; Le Coustumer, G.; Duchenet, V.; Hapiot. P. J. Phys. Chem. 1995, 99, 11923-11929.
92. (b) Facchetti, A.; Yoon, M.-H.; Stern, C. L.: Hutchison, G. R.; Ratner, M. A.; Marks, T. J. J. Am. Chem. Soc. 2004, 126, 13480-13501.
93. (c) Barbarella, G.; Favaretto, L.; Sotgiu, G.; Zambianchi, M.; Fattori, V.; Cocchi, M.; Cacialli, F.: Gigli, G.; Cingolani, R. Adv. Mater. 1999, 11, 1375-1379.