Cyclo-biphenalenyl biradicaloid molecular materials: Conformation, tautomerization, magnetism, and thermochromism

Chemistry of Materials

Volumn 23, Issue 3, 2011, Pages 874-885

  Huang, Jingsong ^a   Sumpter, Bobby G ^a   Meunier, Vincent ^b   Tian, Yong Hui ^c   Kertesz, Miklos ^c  

^a OAK RIDGE NATIONAL LABORATORY   (United States)

^b Rensselaer Polytechnic Institute   (United States)

^c GEORGETOWN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

B3LYP FUNCTIONALS; BOAT CONFORMATIONS; BOND FLUCTUATION; BONDED STRUCTURE; CHAIR CONFORMATIONS; CLOSE-IN; ENERGY DIFFERENCES; GLOBAL MINIMA; MOLECULAR MATERIALS; NEAR ROOM TEMPERATURE; PARAMAGNETIC SUSCEPTIBILITY; PHENALENYL; SIGMATROPIC REARRANGEMENTS; TAUTOMERIZATIONS; THERMOCHROMISM;

BOATS; DIMERS; FUNCTIONAL MATERIALS; PARAMAGNETISM; QUANTUM CHEMISTRY;

CONFORMATIONS;

EID: 79952122983     PISSN: 08974756     EISSN: 15205002     Source Type: Journal    
DOI: 10.1021/cm102320b     Document Type: Article

References (94)

1. (a) Reid, D. H. Chem. Ind. 1956, 1504.
2. (b) Gerson, F. Helv. Chem. Acta 1966, 49, 1463.
3. Zheng, S.; Lan, J.; Khan, S. I.; Rubin, Y. J. Am. Chem. Soc. 2003, 125, 5786.
4. (a) Bag, P.; Itkis, M. E.; Pal, S. K.; Donnadieu, B.; Tham, F. S.; Park, H.; Schlueter, J. A.; Siegrist, T.; Haddon, R. C. J. Am. Chem. Soc. 2010, 132, 2684.
5. (b) Sarkar, A.; Pal, S. K.; Itkis, M. E.; Liao, P. H.; Tham, F. S.; Donnadieu, B.; Haddon, R. C. Chem. Mater. 2009, 21, 2226.
6. (c) Haddon, R. C.; Sarkar, A.; Pal, S. K.; Chi, X. L.; Itkis, M. E.; Tham, F. S. J. Am. Chem. Soc. 2008, 130, 13683.
7. (d) Pal, S. K.; Itkis, M. E.; Tham, F. S.; Reed, R. W.; Oakley, R. T.; Haddon, R. C. J. Am. Chem. Soc. 2008, 130, 3942.
8. (a) Shimizu, A.; Uruichi, M.; Yakushi, K.; Matsuzaki, H.; Okamoto, H.; Nakano, M.; Hirao, Y.; Matsumoto, K.; Kurata, H.; Kubo, T. Angew. Chem., Int. Ed. 2009, 48, 5482.
9. (b) Iketaki, K.; Kanai, K.; Shimizu, A.; Kubo, T.; Wang, Z. H.; Ouchi, Y.; Morita, Y.; Nakasuji, K.; Seki, K. J. Phys. Chem. C 2009, 113, 1515.
10. (c) Kubo, T.; Goto, Y.; Uruichi, M.; Yakushi, K.; Nakano, M.; Fuyuhiro, A.; Morita, Y.; Nakasuji, K. Chem. Asian J. 2007, 2, 1370.
11. (d) Morita, Y.; Aoki, T.; Fukui, K.; Nakazawa, S.; Tamaki, K.; Suzuki, S.; Fuyuhito, A.; Yamamoto, K.; Sato, K.; Shiomi, D.; Naito, A.; Takui, T.; Nakasuji, K. Angew. Chem., Int. Ed. 2002, 41, 1793.
12. (a) Dutta, P.; Maiti, S. K.; Karmakar, S. N. Org. Electron. 2010, 11, 1120.
13. (b) Chang, Y. C.; Chao, I. J. Phys. Chem. Lett. 2010, 1, 116.
14. (c) Yang, W. B.; Wan, X. J.; Chem., Y. S. J. Mol. Struct. 2010, 968, 85.
15. (d) Fan, Z. Q.; Chen, K. Q. Appl. Phys. Lett. 2010, 96, 053509.
16. (e) Yang, W. B.; Wang, X. J.; Xu, Y. F.; Lv, X.; Chen, Y. S. Synth. Met. 2009, 159, 17.
17. (a) Zaitsev, V.; Rosokha, S. V.; Head-Gordon, M.; Kochi, K. J. Org. Chem. 2006, 71, 520.
18. (b) Small, D.; Rosokha, S. V.; Kochi, J. K.; Head-Cordon, M. J. Phys. Chem. A 2005, 109, 11261.
19. (c) Small, D.; Zaitsev, V.; Jung, Y. S.; Rosokha, S. V.; Head-Gordon, M.; Kochi, J. K. J. Am. Chem. Soc. 2004, 126, 13850.
20. (a) Ukai, T.; Nakata, K.; Yamannaka, S.; Kubo, T.; Morita, Y.; Takada, T.; Yamaguchi, K. Polyhedron 2007, 26, 2313.
21. (b) Takano, Y.; Taniguchi, T.; Isobe, H.; Kubo, T.; Morita, Y.; Yamamoto, K.; Nakasuji, K.; Takui, T.; Yamaguchi, K. J. Am. Chem. Soc. 2002, 124, 11122.
22. (c) Takano, T.; Taniguchi, T.; Isobe, H.; Kubo, T.; Morita, Y.; Yamamoto, K.; Nakasuji, K.; Takui, T.; Yamaguchi, K. Chem. Phys. Lett. 2002, 358, 17.
23. (a) Tian, Y.; Kertesz, M. J. Am. Chem. Soc. 2010, 132, 10648.
24. (b) Tian, Y.-H.; Huang, J.; Kertesz, M. Phys. Chem. Chem. Phys. 2010, 12, 5084.
25. (c) Huang, J.; Kertesz, M. J. Phys. Chem. A 2007, 111, 6304.
26. (d) Huang, J.; Kertesz, M. J. Am. Chem. Soc. 2007, 129, 1634.
27. (e) Huang, J.; Kertesz, M. J. Am. Chem. Soc. 2006, 128, 1418.
28. (f) Huang, J.; Kertesz, M. J. Am. Chem. Soc. 2006, 128, 7277.
29. Craciun, S.; Donald, K. J. Inorg. Chem. 2009, 48, 5810.
30. Mota, F.; Miller, J. S.; Novoa, J. J. J. Am. Chem. Soc. 2009, 131, 7699.
31. (a) Pal, S. K.; Itkis, M. E.; Tham, F. S.; Reed, R. W.; Oakley, R. T.; Haddon, R. C. Science 2005, 309, 281.
32. (b) Itkis, M. E.; Chi, X.; Cordes, A. W.; Haddon, R. C. Science 2002, 296, 1443.
33. (c) Morita, Y.; Suzuki, S.; Fukui, K.; Nakazawa, S.; Kitagawa, H.; Kishida, H.; Okamoto, H.; Naito, A.; Sekine, A.; Ohashi, Y.; Shiro, M.; Sasaki, K.; Shiomi, D.; Sato, K.; Takui, T.; Nakasuji, K. Nat. Mater. 2008, 7, 48.
34. (d) Phenalenyl-based molecular materials also display substantial nonlinear optical (NLO) responses, owing to their intermediate biradicaloid character. See for example: Nakao, M.; Kishi, R.; Ohta, S.; Takahashi, H.; Kubo, T.; Kamada, K.; Ohta, K.; Botek, E.; Champagne, B. Phys. Rev. Lett. 2007, 99, 033001.
35. (a) Goto, K.; Kubo, T.; Yamamoto, K.; Nakasuji, K.; Sato, K.; Shiomi, D.; Takui, T.; Kubota, M.; Kobayashi, T.; Yakusi, K.; Ouyang, J. Y. J. Am. Chem. Soc. 1999, 121, 1619.
36. (b) Fukui, K.; Sato, K.; Shiomi, D.; Takui, T.; Itoh, K.; Goto, K.; Kubo, T.; Yamamoto, K.; Nakasuji, K.; Naito, A. Synth. Met. 1999, 103, 2257.
37. Suzuki, S.; Morita, Y.; Fukui, K.; Sato, K.; Shiomi, D.; Takui, T.; Nakasuji, K. J. Am. Chem. Soc. 2006, 128, 2530.
38. Miller, J. S.; Novoa, J. J. Acc. Chem. Res. 2007, 40, 189.
39. Rohrbach, W. D.; Boekelheide, V.; Hanson, A. W. Tetrahedron Lett. 1985, 26, 815.
40. Perdew, J. P.; Schmidt, K. In Density Functional Theory and Its Applications to Materials; Van Doren, V. E., Van Alsenoy C., Geerlings, P., Eds.; AIP Conference Proceedings; American Institute of Physics: Melville, NY, 2001; Vol. 577, pp 1-20.
41. Zhao, Y.; Truhlar, D. G. Acc. Chem. Res. 2008, 41, 157.
42. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
43. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1998, 37, 785.
44. Sousa, S. F.; Fernandes, P. A.; Ramos, M. J. J. Phys. Chem. A 2007, 111, 10439.
45. Parkhill, J. A.; Head-Gordon, M. J. Chem. Phys. 2010, 133, 024103.
46. Bylaska, E. J.; De Jong, W. A.; Govind, N.; Kowalski, K.; Straatsma, T. P.; Valiev, M.; Wang, D.; Apra, E.; Windus, T. L.; Hammond, J. et al. NWChem, A Computational Chemistry Package for Parallel Computers, Version 5.1; Pacific Northwest Laboratory: Richland, WA, 2007
47. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Buran, J. C.; et al.; Gaussian 03, Revision D.01; Gaussian, Inc.: Wallingford, CT, 2004.
48. Chen, Z.; Wannere, C. S.; Corminboeuf, C.; Puchta, R.; Schleyer, P. v. R. Chem. Rev. 2005, 105, 3842.
49. Mayer, I. Chem. Phys. Lett. 1983, 97, 270.
50. Glendening, E. D.; Badenhoop, J, K.; Reed, A. E.; Carpenter, J. E.; Bohmann, J. A.; Morales, C. M.; Weinhold, F. NBO 5.0; Theoretical Chemistry Institute, University of Wisconsin, Madison, WI, 2001.
51. (a) Bacon, A. D.; Zerner, M. C. Theor. Chim. Acta 1979, 53, 21.
52. (b) Ridley, J. E.; Zerner, M. C. Theor. Chim. Acta 1976, 42, 223.
53. (a) Bauernschmitt, R.; Ahlrichs, R. Chem. Phys. Lett. 1996, 256, 454.
54. (b) Casida, M. E.; Jamorski, C.; Casida, K. C.; Salahub, D. R. J. Chem. Phys. 1998, 108, 4439.
55. (c) Stratmann, R. E.; Scuseria, G. E.; Frisch, M. J. J. Chem. Phys. 1998, 109, 8218-24.
56. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A. et al. Gaussian 09, Revision A.02; Gaussian, Inc.: Wallingford CT, 2009.
57. Gajewski, J. J. Hydrocarbon Thermal Isomerizations; Academic Press: New York, 1981; pp 166-76.
58. (a) Staroverov, V. N.; Davidson, E. R. J. Am. Chem. Soc. 2000, 122, 186.
59. (b) Kozlowski, P. M.; Dupius, M.; Davidson, E. R. J. Am. Chem. Soc. 1995, 117, 774.
60. (c) Jiao, H.; Schleyer, P. v. R. Angew. Chem., Int. Ed. 1995, 34, 334.
61. (d) Hrovat, D. A.; Morokuma, K.; Borden, W. T. J. Am. Chem. Soc. 1994, 116, 1072.
62. (e) Wiest, O.; Black, K. A.; Houk, K. N. J. Am. Chem. Soc. 1994, 116, 10336.
63. (f) Dewar, M. J. S.; Jie, C. Acc. Chem. Res. 1992, 25, 537.
64. (a) Staroverov, V. N.; Davidson, E. R. J. Mol. Struct. (THEOCHEM) 2001, 573, 81.
65. (b) Wiest, O. In Encyclopedia of Computational Chemistry; Schleyer, P. v. R., Ed.; Wiley: Chichester, U. K., 1998; Vol. 5, p 3111.
66. (c) Borden, W. T.; Davidson, E. R. Acc. Chem. Res. 1996, 29, 67.
67. (d) Houk, K. N.; Gonzalez, J.; Li, Y. Acc. Chem. Res. 1995, 28, 81.
68. Doering, W. v. E.; Wang, Y. J. Am. Chem. Soc. 1999, 121, 10112.
69. (a) Navarro-Vázquez, A.; Prall, M.; Schreiner, P. R. Org. Lett. 2004, 6, 2981.
70. (b) Hrovat, D. A.; Chen, J.; Houk, K. N.; Borden, W. T. J. Am. Chem. Soc. 2000, 122, 7456.
71. (c) Hrovat, D. A.; Beno, B. R.; Lange, H.; Yoo, H.-Y.; Houk, K. N.; Borden, W. T. J. Am. Chem. Soc. 1999, 121, 10529.
72. (a) Bachrach, S. M. Annu. Rep. Prog. Chem., Sect. B 2008, 104, 394.
73. (b) Armstrong S. K. Molecular rearrangements: part 1. pericyclic reactions. In Organic Reaction Mechanism; Knipe, C, Ed.; John Wiley & Sons: New York, 2010; pp 419-450.
74. (c) Wang Z. Cope Rearrangement. In Comprehensive Organic Name Reactions and Reagents; John Wiley & Sons: Hoboken, NJ, 2009; pp 702-708.
75. Pople, J. A.; Gordon, M. J. Am. Chem. Soc. 1967, 89, 4253.
76. Jung, Y.; Head-Gordon, M. ChemPhysChem 2003, 4, 522.
77. (a) Hammond, G. S. J. Am. Chem. Soc. 1955, 77, 334-338.
78. (b) Solomons, T. W. G.; Fryhle, C. B. Organic Chemistry, 9th ed.; John Wiley & Sons, 2007.
79. Haddon, R. C.; Chow, S.-Y. J. Am. Chem. Soc. 1998, 120, 10494.
80. Friebolin, H. Basic One-and Two-Dimensional NMR Spectroscopy; Wiley-VCH: Weinheim, Germany, 1998.
81. (a) 1.599 Å between two spiro-biphenalenyl neutral radicals: Liao, P.; Itkis, M. E.; Oakley, R. T.; Tham, F. S.; Haddon, R. C. J. Am. Chem. Soc. 2004, 126, 14297.
82. (b) 1.626 Å between two TCNQ anion radicals: Radhakrishnan, T. P.; Van Engen, D.; Soos, Z. G. Mol. Cryst. Liq. Cryst. 1987, 150, 473.
83. 70 anion radicals: Konarev, D. V.; Khasanov, S. S.; Saito, G.; Otsuka, A.; Yoshida, Y.; Lyubovskaya, R. N. J. Am. Chem. Soc. 2003, 125, 10074.
84. Li, Y.; Lampkins, A. J.; Baker, M. B.; Sumpter, B. G.; Huang, J.; Abboud, K. A.; Castellano, R. K. Org. Lett. 2009, 11, 4314.
85. Kahn, O. Molecular Magnetism; VCH Publishers: New York, 1993; pp 5-7, 104.
86. Risko, C.; Kushto, G. P.; Kafati, Z. H.; Brédas, J. L. J. Chem. Phys. 2004, 121, 9031.
87. Gierschner, J.; Mack, H. G.; Oelkrug, D.; Waldner, I.; Rau, H. J. Phy. Chem. A 2004, 108, 257.
88. (a) Garcia-Yoldi, I.; Miller, J. S.; Novoa, J. J. J. Phys. Chem. A 2009, 113, 7124.
89. (b) Huang, J.; Kingsbury, S.; Kertesz, M. Phys. Chem. Chem. Phys. 2008, 10, 2625.
90. Novoa, J. J.; Stephens, P. W.; Weerasekare, M.; Shum, W. W.; Miller, S. S. J. Am. Chem. Soc. 2009, 131, 9070.
91. (a) Wang, F. F.; Wang, Y.; Wang, B. Q.; Wang, Y. F.; Ma, F.; Li, Z. R. Sci. China, Ser. B: Chem. 2009, 52, 1980.
92. (b) Rosokha, S. V.; Kochi, J. K. J. Am. Chem. Soc. 2007, 129, 828.
93. (c) Garcia-Yoldi, I.; Miller, J. S.; Novoa, J. J. J. Phys. Chem. A 2009, 113, 484.
94. (d) Halling, M. D.; Bell, J. D.; Pugmire, R. J.; Grant, D. M.; Miller, J. S. J. Phys. Chem. A 2010, 114, 6622.