Persistent π radical cations: Self-association and its steric control in the condensed phase

Organic and Biomolecular Chemistry

Volumn 3, Issue 4, 2005, Pages 561-569

  Nishinaga, Tohru ^a   Komatsu, Koichi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CONDENSATION; CRYSTAL STRUCTURE; DIMERIZATION; DIMERS; ELECTRONIC STRUCTURE; PARAMAGNETIC RESONANCE; POSITIVE IONS; SPECTROSCOPIC ANALYSIS; THERMODYNAMIC PROPERTIES; X RAY CRYSTALLOGRAPHY;

CONJUGATED OLIGOMERS; RADICAL CATIONS; STERIC CONTROL; STRUCTURAL MODIFICATION;

FREE RADICALS;

EID: 14544272712     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b418872a     Document Type: Review

References (103)

1. N. L. Bauld, Radicals, Ion Radicals, and Triplets, Wiley-VCH, New York, 1997, 141.
2. M. Schmittel and A. Burghart, Angew. Chem., Int. Ed., 1997, 36, 2550.
3. M. Baumgarten and K. Müllen, Top. Curr. Chem., 1994, 169, 1.
4. L. L. Miller and K. R. Mann, Acc. Chem. Res., 1996, 29, 417.
5. For example, S. R. Forrest, Nature, 2004, 428, 911.
6. (a) J. M. Tour, Acc. Chem. Res., 2000, 33, 791;
7. (b) C. Joachim, J. K. Gimzewski and A. Aviram, Nature, 2000, 408, 541;
8. (c) A. Nitzan and M. A. Ratner, Science, 2003, 300, 1384.
9. L. C. Lewis and L. S. Singer, Chem. Phys., 1965, 43, 2712.
10. (a) B. Badger and B. Brocklehurst, Nature (London), 1968, 219, 263;
11. (b) B. Badger and B. Brocklehurst, Trans. Faraday Soc., 1969, 65, 2582 and 2588;
12. (c) B. Badger and B. Brocklehurst, Trans. Faraday Soc., 1970, 66, 2939.
13. M. A. Rodgers, J. Chem. Soc., Faraday Trans., 1972, 68, 1278.
14. J. K. Kochi, R. Rathore and P. L. Magueres, J. Org. Chem., 2000, 65, 6826.
15. For example, P. Batail, K. Boubekeur, M. Fourmigué and J.-C. P. Gabriel, Chem. Mater., 1998, 10, 3005.
16. C. Wurster and R. Sendtner, Chem. Ber., 1879, 12, 1803; C. Wurster and R. Sendtner, Chem. Ber., 1879, 12, 2071.
17. C. Wurster and R. Sendtner, Chem. Ber., 1879, 12, 1803; C. Wurster and R. Sendtner, Chem. Ber., 1879, 12, 2071.
18. H. Wieland, Chem. Ber., 1907, 40, 4260.
19. J. O. Howell, J. M. Goncalves, C. Amatore, L. Klasinc, R. M. Wightman and J. K. Kochi, J. Am. Chem. Soc., 1984, 106, 3968.
20. J. Nakayama and K. Kuroda, J. Am. Chem. Soc., 1993, 115, 4612.
21. F. G. Bordwell and J.-P. Cheng, J. Am. Chem. Soc., 1989, 111, 1792.
22. (a) K. Komatsu, H. Akamatsu, Y. Jinbu and K. Okamoto, J. Am. Chem. Soc., 1988, 110, 633;
23. (b) K. Komatsu, S. Aonuma, Y. Jinbu, R. Tsuji, C. Hirosawa and K. Takeuchi, J. Org. Chem., 1991, 56, 195.
24. A. Matsuura, T. Nishinaga and K. Komatsu, J. Am. Chem. Soc., 2000, 122, 10007.
25. T. Nishinaga, K. Komatsu, N. Sugita, H. J. Lindner and J. Richter, J. Am. Chem. Soc., 1993, 115, 11642.
26. (a) F. Gerson, J. Lopez, R. Akaba and S. F. Nelsen, J. Am. Chem. Soc., 1981, 103, 6716;
27. (b) T. Clark, M. F. Teasley, S. F. Nelsen and H. Wynberg, J. Am. Chem. Soc., 1987, 109, 5719.
28. A. Matsuura, T. Nishinaga and K. Komatsu, Tetrahedron Lett., 1999, 40, 123.
29. A. Matsuura, T. Nishinaga and K. Komatsu, Tetrahedron Lett., 1997, 38, 4125.
30. T. Nishinaga, R. Inoue, A. Matsuura and K. Komatsu, Org. Lett., 2002, 4, 4117.
31. A. Matsuura, T. Nishinaga and K. Komatsu, Tetrahedron Lett., 1997, 38, 3427.
32. A. Wakamiya, T. Nishinaga and K. Komatsu, Chem. Commun., 2002, 1192.
33. T. Nishinaga, A. Wakamiya and K. Komatsu, Tetrahedron Lett., 1999, 40, 4375.
34. (a) A. Wakamiya, D. Yamazaki, T. Nishinaga, T. Kitagawa and K. Komatsu, J. Org. Chem., 2003, 68, 8305;
35. (b) T. Nishinaga, A. Wakamiya, D. Yamazaki and K. Komatsu, J. Am. Chem. Soc., 2004, 126, 3163.
36. - was isolated and was subjected to X-ray crystallography, there was too much disorder around the BCO frameworks.
37. R. E. Del Sesto, J. S. Miller, P. Lafuente and J. J. Novoa, Chem. Eur. J., 2002, 8, 4894.
38. J.-M. Lu, S. V. Rosokha and J. K. Kochi, J. Am. Chem. Soc., 2003, 125, 12161.
39. Because of the similarity between the π-dimer and charge-transfer complex, the transition is occasionally referred to as a "charge-transfer band".
40. J. B. Torrance, B. A. Scott, B. Welber, F. B. Kaufman and P. E. Seiden, Phys. Rev. B: Condens. Matter, 1979, 19, 730.
41. J. L. de Boer and A. Vos, Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem., 1972, 28, 835; J. L. de Boer and A. Vos, Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem., 1972, 28, 839.
42. J. L. de Boer and A. Vos, Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem., 1972, 28, 835; J. L. de Boer and A. Vos, Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem., 1972, 28, 839.
43. C. T. Pott, C. F. van Bruggen and J. Kommandeur, J. Chem. Phys., 1967, 47, 408.
44. J. Tanaka and N. Sakabe, Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem., 1968, 24, 1345.
45. J. Tanaka, M. Inoue, M. Mizuno and K. Horai, Bull. Chem. Soc. Jpn., 1970, 43, 1998.
46. S. Nakayama and K. Suzuki, Bull. Chem. Soc. Jpn., 1973, 46, 3694.
47. F. Effenberger, K.-E. Mack, R. Niess, F. Reisinger, A. Steinbach, W.-D. Sichrer, J. J. Stezowski, I. Rommel and A. Maier, J. Org. Chem., 1988, 53, 4379.
48. J. Heinze, C. Willmann and P. Bäuerle, Angew. Chem. Int. Ed., 2001, 40, 2861.
49. J. S. Miller, D. A. Dixon, J. C. Calabrese, C. Vazquez, P. J. Krusic, M. D. Ward, E. Wasserman and R. L. Harlow, J. Am. Chem. Soc., 1990, 112, 381.
50. R. Rathore and J. K. Kochi, J. Org. Chem., 1995, 60, 4399.
51. R. Rathore, A. S. Kumar, S. V. Lindeman and J. K. Kochi, J. Org. Chem., 1998, 63, 5847.
52. J. Noreland, G. Olovsson and I. Olovsson, Acta Crystallogr, Sect. C: Cryst. Struct. Commun., 1993, 49, 168.
53. M. C. Grossel and S. C. Weston, Chem. Mater., 1996, 8, 977.
54. J. S. Miller, P. J. Krusic, D. A. Dixon, W. M. Reiff, J. H. Zhang, E. C. Anderson and A. J. Epstein, J. Am. Chem. Soc., 1986, 108, 4459.
55. K. Goto, T. Kubo, K. Yamamoto, K. Nakasuji, K. Sato, D. Shiomi, T. Takui, M. Kubota, T. Kobayashi, K. Yakushi and J. Ouyang, J. Am. Chem. Soc., 1999, 121, 1619.
56. R. Sebastiano, J. D. Korp and J. K. Kochi, J. Chem. Soc., Chem. Commun., 1991, 1481.
57. Deprotonation at the 9-position to give the neutral fluorenyl radical, as observed for many fluorenes (F. G. Bordwell, J.-P. Cheng and M. J. Bausch, J. Am. Chem. Soc., 1988, 110, 2867) was not observed.
58. R. S. Glass, Top. Curr. Chem., 1999, 205, 1.
59. There is mechanistic uncertainty as to whether radical-radical coupling or coupling between the radical cation and neutral precursor is operative. See ref. 2.
60. I. Tabakovic, T. Maki, L. L. Miller and Y. Yu, Chem. Commun., 1996, 1911.
61. P. Bäuerle, in Electronic Materials: The Oligomer Approach, ed. K. Müllen and G. Wegner, Wiley, Weinheim, 1998, p. 105.
62. H. Viola and R. Winkler, in Houben veyl: Methoden Organische Chemie, ed. E. Schaumann, Thieme, Stuttgart, 1997, vol. E9a, p. 209.
63. A. Wakamiya, T. Nishinaga and K. Komatsu, J. Am. Chem. Soc., 2002, 124, 15038.
64. G. Klar, in Houben Veyl: Methoden Organische Chemie, ed. E. Schaumann, Thieme, Stuttgart, 1997, vol. E9a, p. 250.
65. T. Nishinaga, A. Wakamiya and K. Komatsu, Chem. Commun., 1999, 777.
66. P. v. R. Schleyer, C. Maerker, A. Dransfeld, H. Jiao and N. J. R. v. E. Hommes, J. Am. Chem. Soc., 1996, 118, 6317.
67. J. Stenhouse, Liebigs Am. Chem., 1869, 149, 247.
68. (a) H. J. Shine and L. Piette, J. Am. Chem. Soc., 1962, 84, 4798;
69. (b) M. Kinoshita and H. Akamatsu, Bull. Chem. Soc. Jpn., 1962, 35, 1040;
70. (c) E. A. C. Lucken, J. Chem. Soc., 1962, 4963.
71. H. Bock, A. Rauschenbach, C. Näther, M. Kleine and Z. Havlas, Chem. Ber., 1994, 127, 2043.
72. W. Hinrichs, P. Berges and G. Klar, Z. Naturforsch., B: Chem. Sci., 1987, 42, 169.
73. M. de Sorgo, B. Wasserman and M. Szwarc, J. Phys. Chem., 1972, 76, 3468.
74. P. Hübler and J. Heinze, Ber. Bunsen-Ges. Phys. Chem., 1998, 102, 1506.
75. P. Rapta, L. Kress, P. Hapiot and L. Dunsch, Phys. Chem. Chem. Phys., 2002, 4, 4181.
76. -1 at 293 K (See section 4.1.).
77. M. Giffard, G. Mabon, E. Leclair, N. Mercier, M. Allain, A. Gorgues, P. Molinié, O. Neilands, P. Krief and V. Khodorkovsky, J. Am. Chem. Soc., 2001, 123, 3852.
78. V. Khodorkovsky, L. Shapiro, P. Krief, A. Shames, G. Mabon, A. Gorgues and M. Giffard, Chem. Commun., 2001, 2736.
79. M. Iyoda, M. Hasegawa, Y. Kuwatani, H. Nishikawa, K. Fukami, S. Nagase and G. Yamamoto, Chem. Lett., 2001, 1146.
80. A. Y. Ziganshina, Y. H. Ko, W. S. Jeon and K. Kim, Chem. Commun., 2004, 806.
81. (a) D. D. Graf, J. P. Campbell, L. L. Miller and K. R. Mann, J. Am. Chem. Soc., 1996, 118, 5480;
82. (b) D. D. Graf, R. G. Duan, J. P. Campbell, L. L. Miller and K. R. Mann, J. Am. Chem. Soc., 1997, 119, 5888.
83. A. Merz, J. Kronberger, L. Dunsch, A. Neudeck, A. Petr and L. Parkanyi, Angew. Chem. Int. Ed., 1999, 38, 1442.
84. (a) M. G. Hill, K. R. Mann, L. L. Miller and J.-F. Penneau, J. Am. Chem. Soc., 1992, 114, 2728;
85. (b) M. G. Hill, J.-F. Penneau, B. Zinger, K. R. Mann and L. L. Miller, Chem. Mater., 1992, 4, 1106;
86. (c) Y. Yu, E. Gunic, B. Zinger and L. L. Miller, J. Am. Chem. Soc., 1996, 118, 1013.
87. (a) P. Bäuerle, U. Segelbacher, K.-U Gaudi, D. Huttenlocher and M. Mehring, Angew. Chem., Int. Ed. Engl., 1993, 32, 76;
88. (b) P. Bäuerle, U. Segelbacher, A. Maier and M. Mehring, J. Am. Chem. Soc., 1993, 115, 10217;
89. (c) P. Bäuerle, T. Fisher, B. Bidlingmeier, A. Stabel and J. Rabe, Angew. Chem., Int. Ed. Engl., 1995, 34, 303.
90. (a) J. A. E. H. van Haare, E. E. Havinga, J. L. J. van Dongen, R. A. J. Janssen, J. Cornil and J.-L. Brédas, Chem. Eur. J., 1998, 4, 1509;
91. (b) J. J. Apperloo, R. A. J. Janssen, P. R. L. Malenfant, L. Groenendaal and J. M. J. Fréchet, J. Am. Chem. Soc., 2000, 122, 7042;
92. (c) J. J. Apperloo, L. Groenendaal, H. Verheyen, M. Jayakannan, R. A. J. Janssen, A. Dkhissi, D. Beljonne, R. Lazzaroni and J.-L. Brédas, Chem. Eur. J., 2002, 8, 2384.
93. (a) H. Nakanishi, N. Sumi, S. Ueno, K. Takimiya, Y. Aso, T. Otsubo, K. Komaguchi, M. Shiotani and N. Ohta, Synth. Met., 2001, 119, 413;
94. (b) T. Satou, T. Sakai, T. Kaikawa, K. Takimiya, T. Otsubo and Y. Aso, Org. Lett., 2004, 6, 997.
95. (a) J. A. E. H. van Haare, L. Groenendaal, E. E. Havinga, R. A. J. Janssen and E. W. Meijer, Angew. Chem., Int. Ed. Engl., 1996, 35, 638;
96. (b) J. A. E. H. van Haare, L. Groenendaal, E. E. Havinga, E. W. Meijer and R. A. J. Janssen, Synth. Met., 1997, 85, 1091;
97. (c) J. A. E. H. van Haare, M. van Boxtel and R. A. J. Janssen, Chem. Mater., 1998, 10, 1166.
98. A. Sakamoto, Y. Furukawa and M. Tasumi, J. Phys. Chem. B, 1997, 101, 1726.
99. E. Levillain and J. Roncali, J. Am. Chem. Soc., 1999, 121, 8760.
100. (a) A. Smie and J. Heinze, Angew. Chem., Int. Ed., 1997, 36, 363;
101. (b) P. Tschuncky, J. Heinze, A. Smie, G. Engelmann and G. Kossmehl, J. Electroanal. Chem., 1997, 433, 223;
102. (c) J. Heinze, P. Tschuncky and A. Smie, J. Solid State Electrochem., 1998, 2, 102.
103. P. Frere, M. Allain, E. H. Elandaloussi, E. Levillain, F.-X. Sauvage, A. Riou and J. Roncali, Chem. Eur. J., 2002, 8, 784.