Novel Fused D-A Dyad and A-D-A Triad Incorporating Tetrathiafulvalene and p-Benzoquinone

Journal of Organic Chemistry

Volumn 69, Issue 6, 2004, Pages 2164-2177

  Dumur, Frédéric ^a   Gautier, Nicolas ^a   Gallego Planas, Nuria ^a   Şahin, Yücel ^a,d   Levillain, Eric ^a   Mercier, Nicolas ^a   Hudhomme, Piétrick ^a   Masino, Matteo ^b   Girlando, Alberto ^b   Lloveras, Vega ^c   Vidal Gancedo, José ^c   Veciana, Jaume ^c   Rovira, Concepció ^c  

^a UNIVERSITÉ D'ANGERS   (France)

^b UNIVERSITY OF PARMA   (Italy)

^c UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

^d ANADOLU UNIVERSITY   (Turkey)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION; CHARGE TRANSFER; CRYSTALLOGRAPHY; ELECTRON SPIN RESONANCE SPECTROSCOPY; FREE RADICALS; OXIDATION; REDUCTION; SYNTHESIS (CHEMICAL);

(ELECTRO)CHEMICAL OXIDATION;

NITROGEN COMPOUNDS;

1,4 BENZOQUINONE; ANION; CATION; RADICAL; TETRATHIAFULVALENE DERIVATIVE;

ARTICLE; CRYSTALLOGRAPHY; CYCLIC POTENTIOMETRY; ELECTRON TRANSPORT; ENERGY ABSORPTION; OXIDATION REDUCTION REACTION; SYNTHESIS; TEMPERATURE DEPENDENCE; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 12144285745     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035689f     Document Type: Article

References (90)

1. (a) Fox, M. A., Chanon, M., Eds.; Photoinduced Electron Transfer; Elsevier: Amsterdam, 1988.
2. (b) Kurreck, H.; Huber M. Angew. Chem., Int. Ed. Engl. 1995, 34, 849.
3. (a) Prasad, P. N.; Williams, D. J. Introduction to Nonlinear Optical Effects in Molecules and Polymers; Wiley: New York, 1991.
4. (b) Nalwa, H. S. Adv. Mater. 1993, 5, 341.
5. (c) Long, N. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 21.
6. (d) Wong, M. S.; Bosshard, C.; Pan, F.; Günter, P. Adv. Mater. 1996, 8, 677.
7. (a) Metzger, R. M.; Panetta, C. New. J. Chem. 1991, 15, 209.
8. (b) Launay J. P. Molecular Electronics. In Granular Nanoelectronics; Ferry, D. K., Ed.; Plenum Press: New York, 1991.
9. (c) Petty, M. C., Bryce, M. R., Bloor, D., Eds.; Introduction to Molecular Electronics; Oxford University Press: New York, 1995.
10. Martín, N.; Sánchez, L.; Illescas, B.; Pérez I. Chem. Rev. 1998, 98, 2527.
11. Yamashita, Y.; Tomura, M. J. Mater. Chem. 1998, 8, 1933.
12. Aviram, A.; Ratner M. Chem. Phys. Lett. 1974, 29, 277.
13. (a) Metzger, R. M.; Chen, B.; Höpfner, U.; Lakshmikantham, M. V.; Vuillaume, D.; Kawai, T.; Wu, X.; Tachibanan, H.; Hughes, T. V.; Sakurai, H.; Hosch, C.; Cava, M. P.; Brehmer, L.; Ashwell, G. J. J. Am. Chem. Soc. 1997, 119, 10455.
14. (b) Metzger, R. M. J. Mater. Chem. 1993, 9, 2027.
15. (c) Metzger, R. M. Acc. Chem. Res. 1999, 32, 950.
16. (d) Roth, S.; Blumentritt, S.; Burghard, M.; Cammi, E.; Carroll, D.; Curran, S.; Düsberg, G.; Liu, K.; Muster, J.; Philipp, G.; Rabenau, T. Synth. Met. 1998, 94, 105.
17. (e) Metzger, R. M. Chem. Rev. 2003, 103, 3803.
18. (a) Segura, J. L.; Martín, N. Angew. Chem., Int. Ed. 2001, 40, 1372.
19. (b) Bryce, M. R. J. Mater. Chem. 2000, 10, 589.
20. (c) Bryce, J. M. Adv. Mater. 1999, 11, 11.
21. Scheib, S.; Cava, M. P.; Baldwin, J. W.; Metzger, R. M. J. Org. Chem. 1998, 63, 1198.
22. Moriarty, R. M.; Tao, A.; Gilardi, R.; Song, Z.; Tuladhar, S. M. Chem. Commun. 1998, 157.
23. (a) Segura, J. L.; Martín, N.; Seoane, C.; Hanack, M. Tetrahedron. Lett. 1996, 37, 2503.
24. (b) Gonzales, M.; Illescas, B.; Martín, N.; Segura, J. L.; Seoane, C.; Hanack, M. Tetrahedron 1998, 54, 2853.
25. Tsiperman, E.; Regev, T.; Becker, J. Y.; Bernstein, J.; Ellern, A.; Khodorkovsky, V.; Shames, A.; Shapiro, L. Chem. Commun. 1999, 1125.
26. Pérez, I.; Liu, S.-G.; Martín, N.; Echegoyen, L. J. Org. Chem. 2000, 65, 3796.
27. Gautier, N.; Mercier, N.; Riou, A.; Gorgues, A.; Hudhomme, P. Tetrahedron Lett. 1999, 40, 5997.
28. (a) Adam, M.; Müllen, K. Adv. Mater. 1994, 6, 439.
29. (b) Frenzel, S.; Müllen, K. Synth. Met. 1996, 175.
30. (a) Watson, W. H.; Eduok, E. E.; Kashyap, R. P.; Krawiec, M. Tetrahedron 1993, 49, 3035.
31. 1/2 = -0.32 V (NHE), but at both negative and positive potentials, the current increases sharply with increasing voltage, giving no distinct oxidation-reduction couples.
32. Some parts of this work have been previously reported: Gautier, N., Dumur, F.; Lloveras, V.; Vidal-Gancedo, J.; Veciana, J.; Rovira, C.; Hudhomme, P. Angew. Chem., Int. Ed. 2003, 42, 2765.
33. Khodorkovsky, V.; Becker J. Y. Organic Conductors, Fundamentals and Applications; Farges, J. P., Ed.; New York, 1994.
34. (a) Synthesis of this compound was carried out according to a previously described methodology, several yields being improved by small modifications of experimental procedures: Sun, D.; Krawiec, M.; Watson, W. H. J. Chem. Crystallogr. 1997, 27, 515.
35. (b) Yields were particularly improved by using piperidine instead of pyrrolidine: Gautier, N.; Gallego-Planas, N.; Mercier, N.; Levillain, E.; Hudhomme, P. Org. Lett. 2002, 4, 961.
36. We should note that an identical reaction using inorganic acids such as hydrochloric acid or sulfuric acid solutions was unsuccessful. In these cases, the resulting precipitate could be the result of concomitant protonation of the TTF core.
37. Boulle, C.; Desmars, O.; Gautier, N.; Hudhomme, P.; Cariou, M.; Gorgues, A. Chem. Commun. 1998, 2197.
38. Phosphonate 17 was synthesized according to well-established procedures from corresponding substituted 1,3-dithiole-2-thione: Moore, A. J.; Bryce, M. R. Synthesis 1991, 26.
39. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martín, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.9; Gaussian, Inc.: Pittsburgh, PA, 1998.
40. Liu, R.; Zhou, X.; Pulay, P. J. Phys. Chem. 1993, 96, 4255 and references therein. Notice that in both Raman and IR, the carbonyl stretching bands are affected by Fermi resonance. We believe that the doublet structure seen in the Raman spectra of 9 and 10a (Figure 2) share the same origin. Accordingly, in the text we report as an approximate frequency the corresponding average.
41. Bozio, R.; Zanon, I.; Girlando, A.; Pecile, C. J. Chem. Phys. 1979, 71, 2282.
42. Hünig, S.; Siunzger, K.; Bau, R.; Metzenthin, T.; Salbeck, J. Chem. Ber. 1993, 126, 465.
43. For references on calculated and experimental UV-visible absorption of cation radical and dication of TTF derivatives, see: (a) Khodorkovsky, V.; Shapiro, L.; Krief, P.; Shames, A.; Mabon, G.; Gorgues, A.; Giffard, M. Chem. Commun. 2001, 2736.
44. (b) Andreu, R.; Garín, J.; Orduna, J. Tetrahedron 2001, 57, 7883.
45. This distortion from planarity between the two dithiolium rings was previously observed on the crystal structure of the dication from the unsymmetrical outer S-position isomer of BEDT-TTF. Hudhomme, P.; Le Moustarder, S.; Durand, C.; Gallego-Planas, N.; Mercier, N.; Blanchard, P.; Levillain, E.; Allain, M.; Gorgues, A.; Riou, A. Chem. Eur. J. 2001, 7, 5070.
46. Giffard, M.; Mabon, G.; Leclair, E.; Mercier, N.; Allain, M.; Gorgues, A.; Molinié, P.; Neilands, O.; Krief, P.; Khodorkovsky, V. J. Am. Chem. Soc. 2001, 123, 3852.
47. Zhao, X.; Imahori, H.; Zhan, C.-G.; Sakata, Y.; Iwata, S.; Kitagawa, T. J. Phys. Chem. 1997, 101, 622.
48. Weil, J. A.; Bolton, J. R.; Wertz, J. E. Electron Paramagnetic Resonance; John Wiley & Sons: New York, 1994.
49. Spectra were recorded at the very beginning of the reduction process, At this stage, the major species present in the solution is the ESR silent neutral compound 9. The observed ESR signal is due to the anion radical, since for statistical reasons dianion radical must have a negligible concentration.
50. H) is the spin density on the nucleus of the hydrogen atom.
51. Hudson, A.; Luckhurst, G. R. Chem. Rev. 1969, 69, 1961.
52. Other organic systems presenting IET between redox centers have been previously reported: (a) Nelsen, F. S.; Thomson-Colon, J. A.; Katfory, M. J. Am. Chem. Soc. 1994, 116, 1589.
53. (b) Bonvoisin, J.; Launay, J.-P.; Rovira, C.; Veciana, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 2106.
54. (c) Lahlil, K.; Moradpour, A.; Bowlas, C.; Menou, F.; Cassoux, P.; Bonvoisin, J.; Launay, J.-P.; Dive, G.; Dehareng, D. J. Am. Chem. Soc. 1995, 117, 9995.
55. (d) Nelsen, F. S.; Ismagilov, R. F.; Trieber, D. A. Science 1997, 278, 846.
56. (e) Lambert, C.; Nöll, G. Angew. Chem., Int. Ed. 1998, 37, 2107.
57. (f) Lambert, C.; Nöll, G. J. Am. Chem. Soc. 1999, 121, 8434.
58. (g) Ruiz-Molina, D.; Sedó, J.; Rovira, C.; Veciana, J. In. Handbook of Advanced Electronic and Photonic Materials and Devices; Nalwa, H. S., Ed.: Academic Press: San Diego, 2001; Vol. 3, p 303.
59. (h) Launay, J. P. Chem. Soc. Rev. 2001, 30, 386.
60. (i) Rovira, C.; Ruiz-Molina, D.; Elsner, O.; Vidal-Gancedo, J.; Bonvoisin, J.; Launay, J.-P.; Veciana, J. Chem.-Eur. J. 2001, 7, 240.
61. (j) Mayor, M.; Büschel, M.; Fromm, K. M.; Lehn, J.-M.; Daub, J. Chem. Eur. J. 2001, 7, 1266.
62. (k) Lambert, C.; Nöll, G.; Schelter, J. Nat. Mater. 2002, 1, 69.
63. (l) Lindeman, S. V.; Rosokha, S. V.; Sun, D.; Kochi, J. K. J. Am. Chem. Soc. 2002, 124, 842.
64. (a) Bumm, L. A.; Arnold, J.; Cygan, M. T.; Dunbar, T. D.; Burgin, T. P.; Jones, L. II; Allara, D. L.; Tour, J. M.; Weiss, P. S. Science 1996 271, 1705.
65. (b) Reed, M. A.; Zhou, C.; Muller, C. J.; Burgin, T. P.; Tour, J. M. Science 1997, 278, 252.
66. (c) Metzger, R. M. Acc. Chem. Res. 1999, 32, 950.
67. (d) Collier, C. P. Wong, E. W.; Belohradsky, M.; Raymo, F. M.; Stoddart, J. F.; Kuekes, P. J.; Williams, R. S.; Heath, J. R. Science 1999, 285, 391.
68. (e) Joachim, C.; Gimzewski, J. K.; Aviram, A. Nature 2000, 408, 541.
69. (f) Tour, J. M. Acc. Chem. Res. 2000, 33, 791.
70. (g) Batchtold, A.; Hadley, P.; Nakanishi, T.; Dekker, C. Science 2001, 294, 1317.
71. (h) Scandola, F., Chiorboli, C., Indelli, M. T., Rampi, M. A., Eds.; Electron Transfer in Chemistry; Wiley-VCH: New York, 2001; Vol. 3.
72. Heinzer, J. Mol. Phys. 1971, 22, 167; Quantum Chemistry Program Exchange 1972, No. 209. We thank Prof. A. Lund for a copy of this program.
73. Heinzer, J. Mol. Phys. 1971, 22, 167; Quantum Chemistry Program Exchange 1972, No. 209. We thank Prof. A. Lund for a copy of this program.
74. Robin, M. B.; Day, P. Adv. Inorg. Chem. Radiochem. 1967, 10, 247. Mixed-valence compounds are classified in three categories: (a) the redox centers are completely localized and behave as separated entities (class I), (b) intermediate coupling between the mixed-valence centers exists (class II), or (c) the system is completely delocalized and the intermediate redox states are attributed to the redox centers (class III).
75. Jozefiak, T. H.; Miller L. L. J. Am. Chem. Soc. 1987, 109, 6560.
76. Jozefiak, T. H.; Almlöf, J. E.; Feyereisen, M. W.; Miller, L. L. J. Am. Chem. Soc. 1989, 111, 4105.
77. Rak, S. F.; Miller, L. L. J. Am. Chem. Soc. 1992, 114, 1388.
78. Becker, J. Y.; Bernstein, J.; Bittner, S.; Levi, N.; Shaik, S. S.; Zer-Zion, N. J. Org. Chem. 1988, 53, 1689 and references therein.
79. Le Paillard, M. P.; Robert, A.; Garrigou-Lagrange, C.; Delhaes, P.; Le Maguerès, P.; Ouahab, L.; Toupet, L. Synth. Met. 1993, 58, 233.
80. (a) Becker, J. Y.; Bernstein, J.; Bittner, S.; Shaik, S. S. Pure Appl. Chem. 1990, 62, 467.
81. (b) Becker, J. Y.; Bernstein, J.; Bittner, S.; Giron, Y.; Harlev, E.; Kaufman-Orenstein, L.; Peleg, D.; Shahal, L.; Shaik, S. S. Synth. Met. 1991, 41-42, 2523.
82. Bondi, A. J. Phys. Chem. 1964, 68, 441.
83. Bond distances suggest a weak intramolecular charge transfer from TTF to benzoquinone moiety; see: Guionneau, P.; Kepert, C. J.; Bravic, D.; Chasseau, D.; Truter, M. R.; Kurmoo, M., Day, P. Synth. Met. 1997, 86, 1973.
84. Chasseau, D.; Gaultier, J.; Fabre, J. M.; Giral, L. Acta Crystallogr. 1982, B38, 1632.
85. Becker, J. Y.; Bernstein, J.; Bittner, S.; Levi, N.; Shaik, S. S. J. Am. Chem. Soc. 1983, 105, 4468.
86. Etter, M. C.; MacDonald, J. C. Acta Crystallogr. 1990, B46, 256.
87. For a review on TCNQ and DCNQI electron acceptors, see: Martín, N.; Segura, J. L.; Seoane, C. J. Mater. Chem. 1997, 7, 1661.
88. Nadizadeh, H.; Mattern, D. L.; Singleton, J.; Wu, X.; Metzger, R. M. Chem. Mater. 1994, 6, 268.
89. (a) Creager, S.; Yu, C. J.; Bamdad, C.; O'Connor, S.; MacLean, T.; Lam, E.; Chong, Y.; Olsen, G. T.; Luo, J.; Gozin, M.; Kayyem, J. F. J. Am. Chem. Soc. 1999, 121, 1059.
90. (b) Caroll, R. L.; Gorman, C. B. Angew. Chem., Int. Ed. 2003, 41, 4378.