Cyclo-meta-phenylene revisited: Nickel-mediated synthesis, molecular structures, and device applications

Journal of Organic Chemistry

Volumn 79, Issue 20, 2014, Pages 9735-9739

  Xue, Jing Yang ^a   Ikemoto, Koki ^b   Takahashi, Norihisa ^a   Izumi, Tomoo ^b,c   Taka, Hideo ^b,c   Kita, Hiroshi ^c   Sato, Sota ^a,b   Isobe, Hiroyuki ^a,b  

^a TOHOKU UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^c Advanced Layer Company Konica Minolta   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DEVICE APPLICATION;

CRYSTALLIN; HYDROCARBON; MACROCYCLIC COMPOUND; NICKEL; PHENAZONE; SOLVENT; UNCLASSIFIED DRUG; [N]CYCLO META PHENYLENE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; CRYSTAL; DEVICES; DIODE; MATERIALS; MOLECULE; ONE POT SYNTHESIS; SOLID STATE; SYNTHESIS;

EID: 84907986082     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo501903n     Document Type: Article

References (55)

1. Iyoda, M.; Yamakawa, J.; Rahman, M. J. Angew. Chem., Int. Ed. 2011, 50, 10522-10553.
2. (a) Rapson, W. S.; Shuttleworth, R. G.; van Niekerk, J. N. J. Chem. Soc. 1943, 326-327.
3. (b) Irngartinger, H.; Reibel, W. R. K. Acta Crystallogr. B 1981, 37, 1724-1728.
4. Wittig, G.; Rümpler, K.-D. Liebigs Ann. Chem. 1971, 751, 1-16.
5. Irngartinger, H. Isr. J. Chem. 1972, 10, 635-647.
6. (e) Ernst, L.; Mannschreck, A.; Rümpler, K.-D. Org. Magn. Reson. 1973, 5, 125-128.
7. For the nomenclature of phenylene macrocycles, we adopted a system that became popular after the synthesis of CPP.
8. (a) Staab, H. A.; Binnig, F. Tetrahedron Lett. 1964, 5, 319-321.
9. (b) Staab, H. A.; Binnig, F. Chem. Ber. 1967, 100, 293-305.
10. (a) Cram, D. J.; Kaneda, T.; Helgeson, R. C.; Lein, G. M. J. Am. Chem. Soc. 1979, 101, 6752-6754.
11. (b) Cram, D. J.; Kaneda, T.; Helgeson, R. C.; Brown, S. B.; Knobler, C. B.; Maverick, E.; Trueblood, K. N. J. Am. Chem. Soc. 1985, 107, 3645-3657.
12. Pisula, W.; Kastler, M.; Yang, C.; Enkelmann, V.; Müllen, K. Chem. - Asian J. 2007, 2, 51-56.
13. Chan, J. M. W.; Swager, T. M. Tetrahedron Lett. 2008, 49, 4912-4914.
14. (a) Jasti, R.; Bhattacharjee, J.; Neaton, J. B.; Bertozzi, C. R. J. Am. Chem. Soc. 2008, 130, 17646-17647.
15. (b) Takaba, H.; Omachi, H.; Yamamoto, Y.; Bouffard, J.; Itami, K. Angew. Chem., Int. Ed. 2009, 48, 6112-6116.
16. Yamago, S.; Watanabe, Y.; Iwamoto, T. Angew. Chem., Int. Ed. 2010, 49, 757-759.
17. (a) Nakanishi, W.; Yoshioka, T.; Taka, H.; Xue, J. Y.; Kita, H.; Isobe, H. Angew. Chem., Int. Ed. 2011, 50, 5323-5326.
18. (b) Nakanishi, W.; Xue, J. Y.; Yoshioka, T.; Isobe, H. Acta Crystallogr., Sect. E: Struct. Rep. Online 2011, E67, o1762-o1763.
19. Xue, J. Y.; Nakanishi, W.; Tanimoto, D.; Hara, D.; Nakamura, Y.; Isobe, H. Tetrahedron Lett. 2013, 54, 4963-4965.
20. (a) Matsuno, T.; Naito, H.; Hitosugi, S.; Sato, S.; Kotani, M.; Isobe, H. Pure Appl. Chem. 2014, 86, 489-495.
21. (b) Matsuno, T.; Kamata, S.; Hitosugi, S.; Isobe, H. Chem. Sci. 2013, 4, 3179-3183.
22. Isobe, H.; Hitosugi, S.; Yamasaki, T.; Iizuka, R. Chem. Sci. 2013, 4, 1293-1297.
23. Hitosugi, S.; Yamasaki, T.; Isobe, H. J. Am. Chem. Soc. 2012, 134, 12442-12445.
24. (e) Hitosugi, S.; Nakanishi, W.; Isobe, H. Chem. - Asian J. 2012, 7, 1550-1552.
25. (f) Hitosugi, S.; Nakanishi, W.; Yamasaki, T.; Isobe, H. Nat. Commun. 2011, 2, 492.
26. g) Nakanishi, W.; Matsuno, T.; Ichikawa, J.; Isobe, H. Angew. Chem., Int. Ed. 2011, 50, 6048-6051.
27. McKinnon, J. J.; Spackman, M. A.; Mitchell, A. S. Acta Crystallogr., Sect. B: Struct. Sci. 2004, B60, 627-668.
28. 2 = 5.8% yield. The yield of [8]CMP was recorded from biphenyl and was 0.72% from m-dibromobenzene.
29. Cram and co-workers reported a six-step synthesis of highly substituted [6]CMP (known as spherand) in 6% yield (ref 5).
30. Müllen and co-workers reported a five-step synthesis of trimethylsilyl-substituted [6]CMP from 1,3,5-tribromobenzene (ref 6). The total yield of trimethylsilyl-substituted [6]CMP was 30%.
31. Swager and co-workers reported Suzuki cross-coupling synthesis of highly functionalized [6]CMP with the yield of 13% (ref 7).
32. (a) Yamamoto, T. Prog. Polym. Sci. 1992, 17, 1153-1205.
33. (b) Yamamoto, T.; Hayashi, Y.; Yamamoto, A. Bull. Chem. Soc. Jpn. 1978, 51, 2091-2097.
34. The major difference between original polymerization conditions and the present conditions is the concentration of the substrate. Yamamoto used a high concentration of 1 M for the polymerization, and we used a diluted concentration of 40 mM for the cyclization.
35. (a) Irngartinger, H.; Leiserowitz, L.; Schmidt, G. M. J. Chem. Ber. 1970, 103, 1132-1156.
36. (b) Irngartinger, H.; Leiserowitz, L.; Schmidt, G. M. J. J. Chem. Soc. B 1970, 497-504.
37. Wolff, S. K.; Grimwood, D. J.; McKinnon, J. J.; Turner, M. J.; Jayatilaka, D.; Spackman, M. A. CrystalExplorer, version 3.1.1; University of Western Australia, 2012.
38. Sato, S.; Yamasaki, T.; Isobe, H. Proc. Natl. Acad. Sci. U. S. A. 2014, 111, 8374-8379.
39. Miyahara, T.; Shimizu, M. J. Cryst. Growth 2001, 229, 553-557.
40. (a) Hummer, G.; Rasaiah, J. C.; Noworyta, J. P. Nature 2001, 414, 188-190.
41. (b) Koga, K.; Gao, G. T.; Tanaka, H.; Zeng, X. C. Nature 2001, 412, 802-805.
42. (a) Koshino, M.; Tanaka, T.; Solin, N.; Suenaga, K.; Isobe, H.; Nakamura, E. Science 2007, 316, 853.
43. (b) Koshino, M.; Solin, N.; Tanaka, T.; Isobe, H.; Nakamura, E. Nat. Nanotechnol. 2008, 3, 595-597.
44. This observation is very similar to that observed for [n]CNAP (ref 9).
45. Melting temperature analysis of Staab showed the decomposition temperature of [6]CMP to be above 500 °C (ref 4).
46. d values were higher (>500 °C).
47. Yersin, H. Highly Efficient OLEDs with Phosphorescent Materials; Wiley: Darmstadt, 2008.
48. Berresheim, A. J.; Müller, M.; Müllen, K. Chem. Rev. 1999, 99, 1747-1785.
49. Ohta, E.; Sato, H.; Ando, S.; Kosaka, A.; Fukushima, T.; Hashizume, D.; Yamasaki, M.; Hasegawa, K.; Muraoka, A.; Ushiyama, H.; Yamashita, K.; Aida, T. Nat. Chem. 2011, 3, 68-73.
50. Hawker, C. J.; Wooley, K. L. Science 2005, 309, 1200-1205.
51. (a) Iwamoto, T.; Watanabe, Y.; Sadahiro, T.; Haino, Y.; Yamago, S. Angew. Chem., Int. Ed. 2011, 50, 8342-8344.
52. (b) Xia, J.; Bacon, J. W.; Jasti, R. Chem. Sci. 2012, 3, 3018-3021.
53. Zabula, A. V.; Filatov, A. S.; Xia, J.; Jasti, R.; Petrukhina, M. A. Angew. Chem., Int. Ed. 2013, 52, 5033-5036.
54. (a) Golder, M. R.; Wong, B. M.; Jasti, R. Chem. Sci. 2013, 4, 4285-4291.
55. (b) Kayahara, E.; Kouyama, T.; Kato, T.; Takaya, H.; Yasuda, N.; Yamago, S. Angew. Chem., Int. Ed. 2013, 52, 13722-13726.