Cyclic 2,12-porphyrinylene nanorings as a porphyrin analogue of cycloparaphenylenes

Journal of the American Chemical Society

Volumn 137, Issue 6, 2015, Pages 2219-2222

  Jiang, Hua Wei ^a   Tanaka, Takayuki ^a   Mori, Hirotaka ^a   Park, Kyu Hyung ^b   Kim, Dongho ^b   Osuka, Atsuhiro ^a  

^a KYOTO UNIVERSITY   (Japan)

^b Yonsei University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

NICKEL; OLIGOMERS; X RAY DIFFRACTION ANALYSIS;

CLOSE PROXIMITY; CYCLIC OLIGOMERS; INTRAMOLECULAR EXCITATIONS; PENTAMERS; PORPHYRIN ARRAYS; REDUCTIVE ELIMINATION; TETRAMERS;

PORPHYRINS;

CHRYSENE; PORPHYRIN DERIVATIVE; PYRENE; TETRAMER; UNCLASSIFIED DRUG; [4]CYCLO 3,9 CHRYSENYLENE; [N]CYCLO 2,12 PORPHYRINYLENE; [N]CYCLOPARAPHENYLENE;

ARTICLE; CATALYST; COLUMN CHROMATOGRAPHY; CRYSTALLIZATION; CYCLIC POTENTIOMETRY; DIFFERENTIAL PULSE VOLTAMMETRY; DRUG CONFORMATION; DRUG SYNTHESIS; ENTROPY; GEL PERMEATION CHROMATOGRAPHY; HYDROGEN BOND; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; NUCLEAR OVERHAUSER EFFECT; OXIDATION REDUCTION POTENTIAL; OXIDATIVE COUPLING; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE; X RAY DIFFRACTION;

EID: 84923260921     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja513102m     Document Type: Article

References (45)

1. Girreser, U.; Giuffrida, D.; Kohnke, F. H.; Mathias, J. P.; Philp, D.; Stoddart, J. F. Pure Appl. Chem. 1993, 65, 119
2. Scott, L. T. Angew. Chem., Int. Ed. 2003, 42, 4133
3. Tahara, K.; Tobe, Y. Chem. Rev. 2006, 106, 5274
4. Kawase, T.; Kurata, H. Chem. Rev. 2006, 106, 5250
5. Eisenberg, D.; Shenhar, R.; Rabinovitz, M. Chem. Soc. Rev. 2010, 39, 2879
6. Iyoda, M.; Yamakawa, J.; Rahman, M. J. Angew. Chem., Int. Ed. 2011, 50, 10522
7. Jasti, R.; Bertozzi, C. R. Chem. Phys. Lett. 2010, 494, 1
8. Omachi, H.; Nakayama, T.; Takahashi, E.; Segawa, Y.; Itami, K. Nat. Chem. 2013, 5, 572
9. Omachi, H.; Segawa, Y.; Itami, K. Acc. Chem. Res. 2012, 45, 1378
10. Hirst, E. S.; Jasti, R. J. Org. Chem. 2012, 77, 10473
11. Sisto, T. J.; Jasti, R. Synlett 2012, 23, 483
12. Yamago, S.; Kayahara, E.; Iwamoto, T. Chem. Rec. 2014, 14, 84
13. Jasti, R.; Bhattacharjee, J.; Neaton, J. B.; Bertozzi, C. R. J. Am. Chem. Soc. 2008, 130, 17646
14. Takaba, H.; Omachi, H.; Yamamoto, Y.; Bouffard, J.; Itami, K. Angew. Chem., Int. Ed. 2009, 48, 6112
15. Yamago, S.; Watanabe, Y.; Iwamoto, T. Angew. Chem., Int. Ed. 2010, 49, 757
16. Hitosugi, S.; Nakanishi, W.; Yamasaki, T.; Isobe, H. Nat. Commun. 2011, 2, 492
17. Iwamoto, T.; Watanabe, Y.; Sakamoto, Y.; Suzuki, T.; Yamago, S. J. Am. Chem. Soc. 2011, 133, 8354
18. Xia, J.; Jasti, R. Angew. Chem., Int. Ed. 2012, 51, 2474
19. Yagi, A.; Segawa, Y.; Itami, K. J. Am. Chem. Soc. 2012, 134, 2962
20. Kayahara, E.; Patel, V. K.; Yamago, S. J. Am. Chem. Soc. 2014, 136, 2284
21. Evans, P. J.; Darzi, E. R.; Jasti, R. Nat. Chem. 2014, 6, 404
22. Yagi, A.; Venkataramana, G.; Segawa, Y.; Itami, K. Chem. Commun. 2014, 50, 957
23. Iwamoto, T.; Kayahara, E.; Yasuda, N.; Suzuki, T.; Yamago, S. Angew. Chem., Int. Ed. 2014, 53, 6430
24. Hitosugi, S.; Yamasaki, T.; Isobe, H. J. Am. Chem. Soc. 2012, 134, 12442
25. Matsuno, T.; Kamata, S.; Hitosugi, S.; Isobe, H. Chem. Sci. 2013, 4, 3179
26. Anderson, S.; Anderson, H. L.; Sanders, J. K. M. Acc. Chem. Res. 1993, 26, 469
27. Satake, A.; Kobuke, Y. Tetrahedron 2005, 61, 13
28. Nakamura, Y.; Aratani, N.; Osuka, A. Chem. Soc. Rev. 2007, 36, 831
29. Aratani, N.; Kim, D.; Osuka, A. Acc. Chem. Res. 2009, 42, 1922
30. Kato, A.; Sugiura, K.; Miyasaka, H.; Tanaka, H.; Kawai, T.; Sugimoto, M.; Yamashita, M. Chem. Lett. 2004, 33, 578
31. Aratani, N.; Osuka, A. Chem. Commun. 2008, 4076
32. Jiang, H.-W.; Ham, S.; Aratani, N.; Kim, D.; Osuka, A. Chem.-Eur. J. 2013, 19, 13328
33. Parkinson, P.; Knappke, C. E. I.; Kamonsutthipaijit, N.; Sirithip, K.; Matichak, J. D.; Anderson, H. L.; Herz, L. M. J. Am. Chem. Soc. 2014, 136, 8217
34. Anderson, H. L.; Sanders, J. K. M. Angew. Chem., Int. Ed. Engl. 1990, 29, 1400
35. Yu, L.; Lindsey, J. J. Org. Chem. 2001, 66, 7402
36. Rucareanu, S.; Schuwey, A.; Gossauer, A. J. Am. Chem. Soc. 2006, 128, 3396
37. OSullivan, M. C.; Sprafke, J. K.; Kondratuk, D. V.; Rinfray, C.; Claridge, T. D. W.; Saywell, A.; Blunt, M.; OShea, J. N.; Beton, P. H.; Malfois, M.; Anderson, H. L. Nature 2011, 469, 72
38. Nakamura, Y.; Hwang, I.-W.; Aratani, N.; Ahn, T. K.; Ko, D. M.; Takagi, A.; Kawai, T.; Matsumoto, T.; Kim, D.; Osuka, A. J. Am. Chem. Soc. 2005, 127, 236
39. Hata, H.; Shinokubo, H.; Osuka, A. J. Am. Chem. Soc. 2005, 127, 8264
40. Shinokubo, H.; Osuka, A. Chem. Commun. 2009, 1011
41. Yorimitsu, H.; Osuka, A. Asian J. Org. Chem. 2013, 2, 356
42. Zhang, X.; Wasinger, E. C.; Muresan, A. Z.; Attenkofer, K.; Jennings, G.; Lindsey, J. S.; Chen, L. X. J. Phys. Chem. A 2007, 111, 11736
43. Segawa, Y.; Omachi, H.; Itami, K. Org. Lett. 2010, 12, 2262
44. Bachrach, S. M.; Stück, D. J. Org. Chem. 2010, 75, 6595
45. George, P.; Trachtman, M.; Bock, C. W.; Brett, A. M. Tetrahedron 1976, 32, 317