Synthesis of tetraphenyl-substituted [12]cycloparaphenylene: Toward a rationally designed ultrashort carbon nanotube

Journal of Organic Chemistry

Volumn 77, Issue 14, 2012, Pages 5857-5860

  Sisto, Thomas J ^a   Tian, Xia ^a   Jasti, Ramesh ^a  

^a Boston University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARMCHAIR CARBON NANOTUBES;

CHEMISTRY; ORGANIC COMPOUNDS;

CARBON NANOTUBES;

CARBON NANOTUBE; PHENYLENEDIAMINE; TETRAPHENYL DICHLORIDE[12]CYCLOPARAPHENYLENE; TETRAPHENYL DIIODIDE DIOL[12]CYCLOPARAPHENYLENE; TETRAPHENYL DIIODIDE[12]CYCLOPARAPHENYLENE; TETRAPHENYL QUINONE[12]CYCLOPARAPHENYLENE; TETRAPHENYL[12]CYCLOPARAPHENYLENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

BENZENE DERIVATIVES; MOLECULAR STRUCTURE; NANOTUBES, CARBON; STEREOISOMERISM;

EID: 84864029126     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo301024g     Document Type: Article

References (25)

1. Scott, L. T.; Jackson, E. A.; Zhang, Q.; Steinberg, B. D.; Bancu, M.; Li, B. J. Am. Chem. Soc. 2012, 134, 107
2. Hitosugi, S.; Nakanishi, W.; Yamasaki, T.; Isobe, H. Nat. Commun. 2011, 2, 492
3. Omachi, H.; Segawa, Y.; Itami, K. Org. Lett. 2011, 13, 2480
4. Jasti, R.; Bertozzi, C. R. Chem. Phys. Lett. 2010, 494, 1
5. Fort, E. H.; Donovan, P. M.; Scott, L. T. J. Am. Chem. Soc. 2009, 131, 16006
6. Fort, E. H.; Scott, L. T. Angew. Chem., Int. Ed. 2010, 49, 6626
7. Fort, E. H.; Scott, L. T. J. Mater. Chem. 2011, 21, 1373
8. Jasti, R.; Bhattacharjee, J.; Neaton, J. B.; Bertozzi, C. R. J. Am. Chem. Soc. 2008, 130, 17646
9. Takaba, H.; Omachi, H.; Yamamoto, Y.; Bouffard, J.; Itami, K. Angew. Chem., Int. Ed. 2009, 48, 6112
10. Omachi, H.; Matsuura, S.; Segawa, Y.; Itami, K. Angew. Chem., Int. Ed. 2010, 49, 10202
11. Yamago, S.; Watanabe, Y.; Iwamoto, T. Angew. Chem., Int. Ed. 2010, 49, 757
12. Iwamoto, T.; Watanabe, Y.; Sakamoto, Y.; Suzuki, T.; Yamago, S. J. Am. Chem. Soc. 2011, 133, 8354
13. Segawa, Y.; Miyamoto, S.; Omachi, H.; Matsuura, S.; Senel, P.; Sasamori, T.; Tokitoh, N.; Itami, K. Angew. Chem., Int. Ed. 2011, 50, 3244
14. Sisto, T. J.; Golder, M. R.; Hirst, E. S.; Jasti, R. J. Am. Chem. Soc. 2011, 133, 15800
15. Xia, J.; Jasti, R. Angew. Chem., Int. Ed. 2012, 51, 2474
16. Li, H.-B.; Page, A. J.; Irle, S.; Morokuma, K. Chem. Phys. Chem. 2012, 13, 1479
17. King, B. T.; Kroulik, J.; Robertson, C. R.; Rempala, P.; Hilton, C. L.; Korinek, J. D.; Gortari, L. M. J. Org. Chem. 2007, 72, 2279
18. Ormsby, J. L.; Black, T. D.; Hilton, C. L.; Bharat; King, B. T. Tetrahedron 2008, 64, 11370
19. Rempala, P.; Kroulik, J.; King, B. T. J. Org. Chem. 2006, 71, 5067
20. Simpson, C. D.; Mattersteig, G.; Martin, K.; Gherghel, L.; Bauer, R. E.; Rader, H. J.; Müllen, K. J. Am. Chem. Soc. 2004, 126, 3139
21. Yang, X.; Dou, X.; Rouhanipour, A.; Zhi, L.; Rader, H. J.; Müllen, K. J. Am. Chem. Soc. 2008, 130, 4216
22. Zhai, L.; Shukla, R.; Wadumethrige, S. H.; Rathore, R. J. Org. Chem. 2010, 75, 4748
23. A similar strategy had been suggested previously for the synthesis of cyclophynes; see: Srinivasan, M.; Sankararaman, S.; Hopf, H.; Varghese, B. Eur. J. Org. Chem. 2003, 660
24. Ullah, I.; Khera, R. A.; Hussain, M.; Villinger, A.; Langer, P. Tetrahedron Lett. 2009, 50, 4651
25. Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685