η6-Cycloparaphenylene transition metal complexes: Synthesis, structure, photophysical properties, and application to the selective monofunctionalization of cycloparaphenylenes

Journal of the American Chemical Society

Volumn 137, Issue 3, 2015, Pages 1356-1361

  Kubota, Natsumi ^a   Segawa, Yasutomo ^a   Itami, Kenichiro ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ATOMS; CHROMIUM COMPOUNDS; COMPLEXATION; METAL COMPLEXES; MOLYBDENUM COMPOUNDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS (CHEMICAL); TRANSITION METAL COMPOUNDS; TRANSITION METALS; TUNGSTEN COMPOUNDS; X RAY CRYSTALLOGRAPHY;

CHEMICAL EQUATIONS; COMPUTATIONAL STUDIES; FUNCTIONALIZATIONS; HOMO-LUMO TRANSITIONS; NUCLEOPHILIC SUBSTITUTIONS; PHOTOPHYSICAL PROPERTIES; TD-DFT CALCULATIONS; X-RAY CRYSTALLOGRAPHIC ANALYSIS;

COORDINATION REACTIONS;

CHROMIUM DERIVATIVE; CYCLOPARAPHENYLENE DERIVATIVE; HYDROGEN; METAL COMPLEX; TRANSITION ELEMENT; TRIMETHYLSILYL DERIVATIVE; UNCLASSIFIED DRUG; BENZENE DERIVATIVE; BRIDGED COMPOUND; ORGANOMETALLIC COMPOUND;

ABSORPTION; ALUMINUM FOIL; ARTICLE; CHEMICAL STRUCTURE; COMPLEX FORMATION; CONFORMATION; CRYSTAL; DIPOLE; ELECTROPHILICITY; ENVIRONMENTAL TEMPERATURE; MASS SPECTROMETRY; NUCLEOPHILICITY; PHYSICAL CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; REACTION TIME; SILYLATION; SOLID STATE; SUBSTITUTION REACTION; SURFACE PROPERTY; SYNTHESIS; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION; CHEMISTRY; PHOTOCHEMISTRY; QUANTUM THEORY;

BENZENE DERIVATIVES; BRIDGED COMPOUNDS; CRYSTALLOGRAPHY, X-RAY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PHOTOCHEMICAL PROCESSES; QUANTUM THEORY; TRANSITION ELEMENTS;

EID: 84921930870     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja512271p     Document Type: Article

References (73)

1. (a) Iyoda, M.; Yamakawa, J.; Rahman, M. J. Angew. Chem., Int. Ed. 2011, 50, 10522.
2. (b) Newkome, G. R.; Sauer, J. D.; Roper, J. M.; Hager, D. C. Chem. Rev. 1977, 77, 513.
3. (c) Zhao, D.; Moore, J. S. Chem. Commun. 2003, 807.
4. (d) Grave, C.; Schlüter, A. D. Eur. J. Org. Chem. 2002, 3075.
5. (e) Höger, S. J. Polym. Sci., Part A: Polym. Chem. 1999, 37, 2685.
6. (a) Fragments of Fullerenes and Carbon Nanotube: Designed Synthesis, Unusual Reactions, and Coordination Chemistry; Petrukhina, M. A., Scott, L. T., Eds.; Wiley: Hoboken, 2012.
7. (b) Steinberg, B. D.; Scott, L. T. Angew. Chem., Int. Ed. 2009, 48, 5400.
8. (c) Fort, E. H.; Scott, L. T. J. Mater. Chem. 2011, 21, 1373.
9. (d) Bunz, U. H. F.; Menning, S.; Martín, N. Angew. Chem., Int. Ed. 2012, 51, 7094.
10. (e) Scott, L. T.; Bronstein, H. E.; Preda, D. V.; Ansems, R. B. M.; Bratcher, M. S.; Hagen, S. Pure Appl. Chem. 1999, 71, 209.
11. (f) Rabideau, P. W.; Sygula, A. Acc. Chem. Res. 1996, 29, 235.
12. (g) Kroto, H. W.; Heath, J. R.; O'Brien, S. C.; Curl, R. F.; Smalley, R. E. Nature 1985, 318, 162.
13. (h) Martin, N.; Sanchez, L.; Illescas, B.; Perez, I. Chem. Rev. 1998, 98, 2527.
14. (i) Ajayan, P. M. Chem. Rev. 1999, 99, 1787.
15. Omachi, H.; Nakamura, T.; Takahashi, E.; Segawa, Y.; Itami, K. Nat. Chem. 2013, 5, 572.
16. (a) Omachi, H.; Segawa, Y.; Itami, K. Acc. Chem. Res. 2012, 45, 1378.
17. (b) Itami, K. Pure Appl. Chem. 2012, 84, 907.
18. (c) Takaba, H.; Omachi, H.; Yamamoto, Y.; Bouffard, J.; Itami, K. Angew. Chem., Int. Ed. 2009, 48, 6112.
19. (d) Omachi, H.; Matsuura, S.; Segawa, Y.; Itami, K. Angew. Chem., Int. Ed. 2010, 49, 10202.
20. (e) Segawa, Y.; Miyamoto, S.; Omachi, H.; Matsuura, S.; Šenel, P.; Sasamori, T.; Tokitoh, N.; Itami, K. Angew. Chem., Int. Ed. 2011, 50, 3244.
21. (f) Segawa, Y.; Šenel, P.; Matsuura, S.; Omachi, H.; Itami, K. Chem. Lett. 2011, 40, 423.
22. (g) Ishii, Y.; Nakanishi, Y.; Omachi, H.; Matsuura, S.; Matsui, K.; Shinohara, H.; Segawa, Y.; Itami, K. Chem. Sci. 2012, 3, 2340.
23. (h) Sibbel, F.; Matsui, K.; Segawa, Y.; Studer, A.; Itami, K. Chem. Commun. 2014, 50, 954.
24. (a) Hirst, E.; Jasti, R. J. Org. Chem. 2012, 77, 10473.
25. (b) Jasti, R.; Bhattacharjee, J.; Neaton, J. B.; Bertozzi, C. R. J. Am. Chem. Soc. 2008, 130, 17646.
26. (c) Sisto, T. J.; Golder, M. R.; Hirst, E. S.; Jasti, R. J. Am. Chem. Soc. 2011, 133, 15800.
27. (d) Xia, J.; Jasti, R. Angew. Chem., Int. Ed. 2012, 51, 2474.
28. (e) Darzi, E. R.; Sisto, T. J.; Jasti, R. J. Org. Chem. 2012, 77, 6624.
29. (f) Yamago, S.; Watanabe, Y.; Iwamoto, T. Angew. Chem., Int. Ed. 2010, 49, 757.
30. (g) Iwamoto, T.; Watanabe, Y.; Sakamoto, Y.; Suzuki, T.; Yamago, S. J. Am. Chem. Soc. 2011, 133, 8354.
31. (h) Kayahara, E.; Sakamoto, Y.; Suzuki, T.; Yamago, S. Org. Lett. 2012, 14, 3284.
32. (i) Kayahara, E.; Iwamoto, T.; Suzuki, T.; Yamago, S. Chem. Lett. 2013, 42, 621.
33. (j) Evans, P. J.; Darzi, E. R.; Jasti, R. Nat. Chem. 2014, 6, 404.
34. (k) Kayahara, K.; Patel, V. K.; Yamago, S. J. Am. Chem. Soc. 2014, 136, 2284.
35. (a) Omachi, H.; Segawa, Y.; Itami, K. Org. Lett. 2011, 13, 2480.
36. (b) Yagi, A.; Segawa, Y.; Itami, K. J. Am. Chem. Soc. 2012, 134, 2962.
37. (c) Matsui, K.; Segawa, Y.; Itami, K. Org. Lett. 2012, 14, 1888.
38. (d) Matsui, K.; Segawa, Y.; Namikawa, T.; Kamada, K.; Itami, K. Chem. Sci. 2013, 4, 84.
39. (e) Ishii, Y.; Matsuura, S.; Segawa, Y.; Itami, K. Org. Lett. 2014, 16, 2174.
40. (f) Sisto, T. J.; Tian, X.; Jasti, R. J. Org. Chem. 2012, 77, 5857.
41. (g) Nishiuchi, T.; Feng, X.; Enkelmann, V.; Wagner, M.; Müllen, K. Chem. - Eur. J. 2012, 18, 16621.
42. (h) Golling, F. E.; Quernheim, M.; Wagner, M.; Nishiuchi, T.; Müllen, K. Angew. Chem., Int. Ed. 2014, 53, 1525.
43. (i) Xia, J.; Golder, M. R.; Foster, M. E.; Wong, B.; Jasti, R. J. Am. Chem. Soc. 2012, 134, 19709.
44. (j) Hitosugi, S.; Nakanishi, W.; Yamasaki, T.; Isobe, H. Nat. Commun. 2011, 2, 492.
45. (k) Hitosugi, S.; Nakanishi, W.; Isobe, H. Chem. - Asian J. 2012, 7, 1550.
46. (l) Hitosugi, S.; Yamasaki, T.; Isobe, H. J. Am. Chem. Soc. 2012, 134, 12442.
47. (m) Matsuno, S.; Kamata, S.; Hitosugi, S.; Isobe, H. Chem. Sci. 2013, 4, 3179.
48. (n) Isobe, H.; Hitosugi, S.; Yamasaki, T.; Iizuka, R. Chem. Sci. 2013, 4, 129.
49. (o) Iwamoto, T.; Kayahara, E.; Yasuda, N.; Suzuki, T.; Yamago, S. Angew. Chem., Int. Ed. 2014, 53, 6430.
50. (p) Matsui, K.; Segawa, Y.; Itami, K. J. Am. Chem. Soc. 2014, 136, 16452.
51. (q) Ito, H.; Mitamura, Y.; Segawa, Y.; Itami, K. Angew. Chem., Int. Ed. 2015, 54, 159.
52. (a) Segawa, Y.; Omachi, H.; Itami, K. Org. Lett. 2010, 12, 2262.
53. (b) Segawa, Y.; Fukazawa, A.; Matsuura, S.; Omachi, H.; Yamaguchi, S.; Irle, S.; Itami, K. Org. Biomol. Chem. 2012, 10, 5979.
54. (c) Nishihara, T.; Segawa, Y.; Itami, K.; Kanemitsu, Y. J. Phys. Chem. Lett. 2012, 3, 3125.
55. (d) Camacho, C.; Niehaus, T. A.; Itami, K.; Irle, S. Chem. Sci. 2013, 4, 187.
56. (e) Nishihara, T.; Segawa, Y.; Itami, K.; Kanemitsu, Y. Chem. Sci. 2014, 5, 2293.
57. (f) Fujitsuka, M.; Cho, D. W.; Iwamoto, T.; Yamago, S.; Majima, T. Phys. Chem. Chem. Phys. 2012, 14, 14585.
58. (g) Fujitsuka, M.; Lu, C.; Iwamoto, T.; Kayahara, E.; Yamago, S.; Majima, T. J. Phys. Chem. A 2014, 118, 4527.
59. (h) Adamska, L.; Nayyar, I.; Chen, H.; Swan, A. K.; Oldani, N.; Fernandez-Alberti, S.; Golder, M. R.; Jasti, R.; Doorn, S. K.; Tretiak, S. Nano Lett. 2014, 14, 6539.
60. (a) Iwamoto, T.; Watanabe, Y.; Sadahiro, T.; Haino, T.; Yamago, S. Angew. Chem., Int. Ed. 2011, 50, 8342.
61. (b) Xia, J.; Bacon, J. W.; Jasti, R. Chem. Sci. 2012, 3, 3018.
62. (c) Iwamoto, T.; Watanabe, Y.; Takaya, H.; Haino, T.; Yasuda, N.; Yamago, S. Chem. - Eur. J. 2013, 19, 14061.
63. (d) Nakanishi, Y.; Omachi, H.; Matsuura, S.; Miyata, Y.; Kitaura, R.; Segawa, Y.; Itami, K.; Shinohara, H. Angew. Chem., Int. Ed. 2014, 53, 3102.
64. (e) Alvarez, M. P.; Burrezo, P. M.; Kertesz, M.; Iwamoto, T.; Yamago, S.; Xia, J.; Jasti, R.; Navarrete, J. T. L.; Taravillo, M.; Baonza, V. G.; Casado, J. Angew. Chem., Int. Ed. 2014, 53, 7033.
65. (f) Iwamoto, T.; Slanina, Z.; Mizorogi, N.; Guo, J.; Akasaka, T.; Nagase, S.; Takaya, H.; Yasuda, N.; Kato, T.; Yamago, S. Chem. - Eur. J. 2014, 20, 14403.
66. (g) PeñaAlvarez, M.; Burrezob, P. M.; Iwamoto, T.; Taravilloa, M.; Baonzaa, V. G.; Navarreteb, J. T. L.; Yamago, S.; Casado, J. Faraday Discuss. 2014, 173, 157.
67. Zabula, A. V.; Filatov, A. S.; Xia, J.; Jasti, R.; Petrukhina, M. A. Angew. Chem., Int. Ed. 2013, 52, 5033.
68. (a) Kündig, E. P. In Topics in Organometallic Chemistry; Springer: Berlin, 2004; Vol. 7.
69. (b) Rosillo, M.; Domínguez, G.; Pérez-Castells, J. Chem. Soc. Rev. 2007, 36, 1589.
70. (a) Zhu, N.; Zhang, G.-B.; Xie, R.-J.; Han, L.-M.; Hong, H.-L.; Liu, Z.-S.; Suo, Q.-L. J. Coord. Chem. 2011, 64, 2361.
71. (b) Baker, M. V.; North, M. R. J. Organomet. Chem. 1998, 565, 225.
72. Fulmer, G. R.; Miller, A. J. M.; Sharden, N. H.; Gottlieb, H. E.; Nudelan, A.; Stoltz, B. M.; Bercaw, J. E.; Goldberg, K. I. Organometallics 2010, 29, 2176.
73. Tokyo Chemical Industry Co., Ltd. (TCI), catalog no. C2449 ([12]CPP); Kanto Chemical Co., Inc. catalog no. 08131-35 ([9]CPP), 08132-35 ([12]CPP), 08137-65 ([15]CPP).