Persistent and Transient Open-Shell Species Derived from C60-TTF Cyclohexene-Fused Dyads

Journal of Organic Chemistry

Volumn 63, Issue 15, 1998, Pages 5201-5210

  Llacay, Josep ^a   Veciana, Jaume ^a   Vidal Gancedo, José ^a   Bourdelande, José Luis ^a   González Moreno, Rafael ^a   Rovira, Concepció ^a  

^a UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000166703     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980498b     Document Type: Article

References (65)

1. Krästchmer, W.; Lamb, L. D.; Fostiropoulos, K.; Huffman, D. R. Nature 1990, 347, 354.
2. Xie, Q.; Pérez-Cordero, E.; Echegoyen, L. J. Am. Chem. Soc. 1992, 114, 3978.
3. (a) Prato, M. J. Mater. Chem. 1997, 7, 1097.
4. (b) Rubin, Y.; Khan, S.; Freedberg, D. I.; Yeretzian, C. J. Am. Chem. Soc. 1993, 115, 344.
5. (c) Rubin, Y.; Khan, S. I.; Oliver, A. M.; Paddon-Row, M. N. Ibid. 1993, 115, 4919.
6. (d) Mullen, K.; Belik, P.; Gügel, A.; Spickermann, J. Angew. Chem., Int. Ed. Engl. 1993, 32, 78.
7. (e) Liddell, P.; Mcpherson, A. N.; Sumida, J.; Demanche, L.; Moore, A. L.; Moore, T. A.; Gust, D. Photochem, Photobiol. 1994, 595, 365.
8. (f) Linssen, T. G.; Dürr, K.; Hanack, M.; Hirsch, A. J. Chem. Soc., Chem. Commun. 1995, 103.
9. Matsubara, Y.; Tada H.; Nagase, S.; Yoshida, Z. J. Org. Chem. 1995, 60, 5372.
10. (a) Lawsom, J. M.; Oliver, A. M.; Rothenfluh, D. F.; An, Y.-Z.; Ellis, G. A.; Ranasinghe, M. G.; Khan, S. I.; Franz, A. G.; Ganapathi, P. S.; Shephard, M. J.; Paddon-Row, M. N.; Rubin, Y. J. Org.Chem. 1996, 61, 5032.
11. (b) Williams, R. M.; Koeberg, M.; Lawson, J. M.; An, Y.-Z.; Rubin. Y.; Paddon-Row, M. N.; Verhoeven, J. W. Ibid. 1996, 61, 5055.
12. (c) Williams, R. M.; Zwier, J. M.; Verhoeven, J. W. J. Am. Chem. Soc. 1995, 117, 4093.
13. (a) Kuciauskas, S.; Lin, S.; Seely, G. R.; Moore, A. L.; Moore T. A.; Gust, D.; Drovetskaya, T.; Reed, C. A.; Boyd, P. D. W. J. Phys. Chem. 1996, 100, 15926.
14. (b) Liddell, P. A.; Kuciauskas, S.; Sumida, J. P.; Nash, B.; Nguyen, D.; Moore, A. L.; Moore, T. A.; Gust, D. J. Am. Chem. Soc. 1997, 119, 1400.
15. (a) Sariciftci, N. S.; Wudl, F.; Heeger, A. J.; Maggini, M.; Scorrano, G.; Prato, M. Bourassa, J.; Ford, P. C. Chem. Phys. Lett. 1995, 247, 510.
16. (b) Guldi, D. M.; Maggini, M.; Scorrano, G.; Prato, M. J. Am. Chem. Soc. 1997, 119, 974.
17. (a) Imahori, H.; Hagiwara, K.; Aoki, M.; Akiyama, T.; Taniguchi, S.; Okada, T.; Shirakawa, M.; Sakata, Y. J. Am. Chem. Soc. 1996, 118, 11771.
18. (b) Imahori, H.; Sakata, Y. Adv. Mater. 1997, 9, 537.
19. (c) Sakata, Y.; Imahori, H.; Tsue, H.; Higashida, S.; Akiyama, T.; Yoshizawa, E.; Aoki, M.; Yamada, K.; Hagiwara, K.; Taniguchi, S.; Okada, T. Pure Appl. Chem. 1997, 69, 1951.
20. Williams, J. M.; Ferraro, J. R.; Thorn, R. J.; Carlson, K. D.; Geiser, U.; Wang, H. H.; Kini, A. M.; Whangbo, M.-H. Organic Superconductors; Prentice Hall: Englewood Cliffs, NJ, 1992.
21. Izouka, A.; Tachikawa, T.; Sugawara, T.; Suzuki, Y.; Konno, M.; Saito, Y.; Shinohara, H. J. Chem. Soc., Chem. Commun. 1992, 1472.
22. Metzger, R. M.; Cava, M. P.; Shcherbakova, I.; Lee, W. J.; Wang, P. Synth. Met. 1994, 64, 319.
23. Saito, G.; Teramoto, T.; Otsuka, A.; Sugita, Y.; Ban, T.; Kusunoki, M.; Sakagughi, K. Synth. Met. 1994, 64, 359.
24. (a) Llacay, J.; Tarrés, J.; Veciana, J.; Rovira, C. Synth. Met. 1995, 70, 1453.
25. (b) Llacay, J.; Mas, M.; Molins, E.; Rovira, C.; Veciana, J. J. Phys. Chem. Solids 1997, 58, 1675.
26. Prato, M.; Maggini, M.; Giacometti, C.; Scorrano, G.; Sandonà, G.; Farina, G. Tetrahedron 1996, 52, 5221.
27. (a) Martín, N.; Sánchez, L.; Seoane, C.; Andreu, R.; Garín, J.; Orduna, J. Tetrahedron Lett. 1996, 37, 5979.
28. (b) Martín, N.; Pérez, I.; Sánchez, L.; Seoane, C. J. Org. Chem. 1997, 62, 5690.
29. A preliminary account on the synthesis of the dyad 1a and cycloadduct 4, as well as on the crystal structure of last compound, has been recently published: Llacay, J.; Mas, M.; Molins, E.; Veciana, J.; Rovira, C. Chem. Commun. 1997, 659.
30. Hirsch, A. The Chemistry of the Fullerenes; Thieme: New York, 1994.
31. Narita, M.; Pittman, C. U. Synthesis 1976, 489.
32. Inomata, K.; Kinoshita, H.; Takemoto, H.; Murata, Y.; Kotake, H. Bull. Chem. Soc. Jpn. 1978, 51, 3341.
33. Yamada, S.; Ohsawa, H.; Suzuki, T.; Takayama, H. J. Org. Chem. 1986, 51, 4934.
34. Homocoupling attempts were carried out using various coupling agents, including neat trimethyl phosphite, triethyl phosphite, and triphenyl phosphite, as well as toluene/phosphite mixtures. Several 1,3-dithiole-2-chalcogen systems were also used in order to obtain dyads 1, but the desired compounds were not detected in the reaction mixtures, and the starting compound 4 was always recovered almost quantitatively.
35. Boulle, C.; Cariou, M.; Bainville, M.; Gorgues, A.; Hudhomme, P.; Orduna, J.; Garín, J. Tetrahedron Lett. 1996, 38, 81.
36. Veciana, J.; Rovira, C.; Cowan, D. Tetrahedron Lett. 1988, 29, 3467.
37. Llacay, J.; Mata, I.; Molins, E.; Rovira, C.; Veciana, J. Adv. Mat. 1998, 3, 330.
38. 3. The electrical conductivity of single crystals was measured with the four-probes method, revealing an insulator (R > 20 MΩ) behavior. The growth of single crystals of dyads 1b and 1c turned out to be even more difficult than for dyad 1a.
39. Nakamura, Y.; Minowa, T.; Tobita, S.; Shizuka, H.; Nishimura, J. J. Chem. Soc., Perkin Trans. 2 1995, 2351.
40. Suzuki, T.; Maruyama, Y.; Akasaba, T.; Ando, W.; Kobayashi K.; Nagase, S. J. Am. Chem. Soc. 1994, 116, 1359.
41. Chlistunoff, J.; Cliffel, D.; Bard, A. J. In Handbook of Organic Conductive Molecules and Polymers; Nalwa, H. S., Ed.; John Wiley & Sons Ltd.: New York, 1997; Vol. 1, Chapter 7.
42. Brezová, V.; Gügel, A.; Rapta, P.; Stasko, A. J. Phys. Chem. 1996, 100, 16232.
43. Jones, M. T.; Kadish, K. M.; Subramanian, R.; Boulas, P.; Vijayashree M. N. Synth. Met. 1995, 70, 1341.
44. (a) Sun Y.; Drovetskaya, T.; Bolskar, R. D.; Bau, R.; Boyd, P. D. W.; Reed, C. A. J. Org. Chem. 1997, 62, 3642.
45. (b) Baumgarten, M.; Ghergel, L. Progress in Fullerene Research; World Scientific: Singapore, 1994; pp 348-388.
46. Baumgarten, M.; Gügel, A.; Ghergel, L. Adv. Mater. 1993, 458.
47. Khaled, M. M.; Carlin, R. T.; Trulove, P. C.; Eaton, G. R.; Eaton, S. S. J. Am. Chem. Soc. 1994, 116, 3465.
48. Staško, A.; Brezová, V.; Biskupic, S.; Dinse, K.-P.; Schweitzer, P.; Baumgarten, M. J. Phys. Chem. 1995, 99, 8782.
49. We are currently working in the isolation of pure regioisomers of 1d in order to study the different spin density distribution resulting from the distinct substitution patterns.
50. Baumgarten, M.; Ghergel, L. Synth. Met. 1995, 70, 1389.
51. Torrance, J. B.; Scott, B. A.; Weiber, B.; Kaufman, F. B.; Seiden, P. E. Phys. Rev. B 1979, 19, 730.
52. Talham, D. R.; Chou, L.-K.; Quijada, M. A.; Clevenger, M. B.; Oliveira, G. F. d.: Abboud, K. A.; Tanner, D. B. Chem. Mater. 1995, 7, 530.
53. (a) Cavara, L.; Gerson, F.; Cowan, D. O.; Lerstrup, K. Helv. Chim. Acta 1986, 69, 141.
54. (b) Rovira, C.; Veciana, J.; Santaló, N.; Tarrés, J.; Cirujeda, J.; Molins, E.; Llorca, J.; Espinosa, E. J. Org. Chem. 1994, 59, 3307.
55. 16 These optimized geometries present two sets of hydrogen atoms; one set of two atoms forming an angle a of 13° between the C-H bond and the plane defined by the TTF core and the other set of two hydrogen atoms forming an angle β of 106°.
56. (a) Rubin, Y.; Khan, S.; Freedberg, D. I.; Yeretzian, C. J. Am. Chem. Soc. 1993, 115, 344.
57. (b) Tago, T.; Minowa, T.; Okada, Y.; Nishimura, J. Tetrahedron Lett. 1993, 34, 8461.
58. Zhang, X.; Foote, C. S. J. Org. Chem. 1994, 59, 5235.
59. Fernández-Paniagua, U. M.; Illescas, B.; Martín, N.; Seoane, C.; Cruz, P.; Hoz, A.; Langa, F. J. Org. Chem. 1997, 62, 3705.
60. Along with this maximum, another one was also observed around 390 nm with a lower abosrbance that deactivates exponentially at the same rate as the first maximum for all the studied dyads.
61. .- expected at around 1010 nm for these charge-separated species lies outside the limit of our detector.
62. Arena, F.; Bullo, F.; Conti, F.; Corvaja, C. Maggini, M.; Prato, M.; Scorrano, G. J. Am. Chem. Soc. 1997, 119, 789.
63. For a semiempirical AM1 method, see: Dewar, M. J. S.; Zoebisch, E. G.; Healey, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902. For MOPAC 93, see: Stewart, J. J. P. MOPAC 93; Fujitsu Limited: Tokyo, Japan, 1993.
64. For a semiempirical AM1 method, see: Dewar, M. J. S.; Zoebisch, E. G.; Healey, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902. For MOPAC 93, see: Stewart, J. J. P. MOPAC 93; Fujitsu Limited: Tokyo, Japan, 1993.
65. Terahara, A.; Ohya-Nishiguchi, H.; Hirota, N.; Awaji, H.; Kawase, T.; Yoneda, S.; Sugimoto, T.; Yoshida, Z.-i. Bull. Chem. Soc. Jpn. 1984, 57, 1760.