Synthesis of cycloparaphenylenes and related carbon nanorings: A step toward the controlled synthesis of carbon nanotubes

Accounts of Chemical Research

Volumn 45, Issue 8, 2012, Pages 1378-1389

  Omachi, Haruka ^a   Segawa, Yasutomo ^a   Itami, Kenichiro ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; CARBON NANOTUBE;

ARTICLE; CHEMISTRY; METHODOLOGY; NANOTECHNOLOGY; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

BENZENE; CHEMISTRY TECHNIQUES, SYNTHETIC; CRYSTALLOGRAPHY, X-RAY; NANOTECHNOLOGY; NANOTUBES, CARBON; STEREOISOMERISM;

EID: 84865322985     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar300055x     Document Type: Article

References (52)

1. Iijima, S. Helical microtubules of graphitic carbon Nature 1991, 354, 56-58
2. Carbon Nanotubes: Synthesis, Properties and Applications; Dresselhaus, M.; Dresselhaus, G.; Avouris, Ph., Eds.; Springer: Berlin, 2001.
3. Dai, H. J. Carbon nanotubes: synthesis, integration, and properties Acc. Chem. Res. 2002, 35, 1035-1044
4. Coleman, J. N.; Khan, U.; Blau, W. J.; Gun'ko, Y. K. Small but strong: A review of the mechanical properties of carbon nanotube-polymer composites Carbon 2006, 44, 1624-1652
5. Carlson, L. J.; Krauss, T. D. Photophysics of individual single-walled carbon nanotubes Acc. Chem. Res. 2008, 41, 235-243
6. Zhang, M.; Fang, S.; Zakhidov, A. A.; Lee, S. B.; Aliev, A. E.; Williams, C. D.; Atkinson, K. R.; Baughman, R. H. Strong, transparent, multifunctional, carbon nanotube sheets Science 2005, 309, 1215-1219
7. Wu, Z. C.; Chen, Z. H.; Du, X.; Logan, J. M.; Sippel, J.; Nikolou, M.; Kamaras, K.; Reynolds, J. R.; Tanner, D. B.; Hebard, A. F.; Rinzler, A. G. Transparent, conductive carbon nanotube films Science 2004, 305, 1273-1276
8. Heller, D. A.; Baik, S.; Eurell, T. E.; Strano, M. S. Single-walled carbon nanotube spectroscopy in live cells: Towards long-term labels and optical sensors Adv. Mater. 2005, 17, 2793-2799
9. Dresselhaus, M. S.; Dresselhaus, G.; Saito, R. Physics of carbon nanotubes Carbon 1995, 33, 883-891
10. Fort, E. H.; Donovan, P. M.; Scott, L. T. Diels-Alder reactivity of polycyclic aromatic hydrocarbon bay regions: Implications for metal-free growth of single-chirality carbon nanotubes J. Am. Chem. Soc. 2009, 131, 16006-16007
11. Fort, E. H.; Scott, L. T. One-step conversion of aromatic hydrocarbon bay regions into unsubstituted benzene rings: A reagent for the low-temperature, metal-free growth of single-chirality carbon nanotubes Angew. Chem., Int. Ed. 2010, 49, 6626-6628
12. Fort, E. H.; Scott, L. T. Carbon nanotubes from short hydrocarbon templates. Energy analysis of the Diels-Alder cycloaddition/rearomatization growth strategy J. Mater. Chem. 2011, 21, 1373-1381
13. Bodwell, G. J. Carbon nanotubes: Growth potential Nat. Nanotechnol. 2010, 5, 103-104
14. Jasti, R.; Bertozzi, C. R. Progress and challenges for the bottom-up synthesis of carbon nanotubes with discrete chirality Chem. Phys. Lett. 2010, 494, 1-7
15. Smalley, R. E.; Li, Y.; Moore, V. C.; Price, B. K.; Colorado, R.; Schmidt, H. K.; Hauge, R. H.; Barron, A. R.; Tour, J. M. Single wall carbon nanotube amplification: En route to a type-specific growth mechanism J. Am. Chem. Soc. 2006, 128, 15824-15829
16. 60 to single-walled carbon nanotubes Nano Lett. 2010, 10, 3343-3349
17. Gleiter, R.; Esser, B.; Kornmayer, S. C. Cyclacenes: Hoop-shaped systems composed of conjugated rings Acc. Chem. Res. 2009, 42, 1108-1116
18. Takaba, H.; Omachi, H.; Yamamoto, Y.; Bouffard, J.; Itami, K. Selective synthesis of [12]cycloparaphenylene Angew. Chem., Int. Ed. 2009, 48, 6112-6116
19. Segawa, Y.; Omachi, H.; Itami, K. Theoretical studies on the structures and strain energies of cycloparaphenylenes Org. Lett. 2010, 12, 2262-2265
20. Omachi, H.; Matsuura, S.; Segawa, Y.; Itami, K. A modular and size-selective synthesis of [ n ]cycloparaphenylenes: A step toward the selective synthesis of [ n, n ]single-walled carbon nanotubes Angew. Chem., Int. Ed. 2010, 49, 10202-10205
21. Segawa, Y.; Miyamoto, S.; Omachi, H.; Matsuura, S.; Šenel, P.; Sasamori, T.; Tokitoh, N.; Itami, K. Concise synthesis and crystal structure of [12]cycloparaphenylene Angew. Chem., Int. Ed. 2011, 50, 3244-3248
22. Segawa, Y.; Šenel, P.; Matsuura, S.; Omachi, H.; Itami, K. [9]Cycloparaphenylene: Nickel-mediated synthesis and crystal structure Chem. Lett. 2011, 40, 423-425
23. Yagi, A.; Segawa, Y.; Itami, K. Synthesis and properties of [9]cyclo-1,4-naphthylene: A π-extended carbon nanoring J. Am. Chem. Soc. 2012, 134, 2962-2965
24. Omachi, H.; Segawa, Y.; Itami, K. Synthesis and racemization process of chiral carbon nanorings: A step toward the chemical synthesis of chiral carbon nanotubes Org. Lett. 2011, 13, 2480-2483
25. Jasti, R.; Bhattacharjee, J.; Neaton, J. B.; Bertozzi, C. R. Synthesis, characterization, and theory of [9]-, [12]-, and [18]cycloparaphenylene: Carbon nanohoop structures J. Am. Chem. Soc. 2008, 130, 17646-17647
26. Yamago, S.; Watanabe, Y.; Iwamoto, T. Synthesis of [8]cycloparaphenylene from a square-shaped tetranuclear platinum complex Angew. Chem., Int. Ed. 2010, 49, 757-759
27. Iwamoto, T.; Watanabe, Y.; Sakamoto, Y.; Suzuki, T.; Yamago, S. Selective and random syntheses of [ n ]cycloparaphenylenes (n = 8-13) and size dependence of their electronic properties J. Am. Chem. Soc. 2011, 133, 8354-8361
28. Sisto, T. J.; Golder, M. R.; Hirst, E. S.; Jasti, R. Selective synthesis of strained [7]cycloparaphenylene: An orange-emitting fluorophore J. Am. Chem. Soc. 2011, 133, 15800-15802
29. Xia, J.; Jasti, R. Synthesis, characterization, and crystal structure of [6]cycloparaphenylene Angew. Chem., Int. Ed. 2012, 51, 2474-2476
30. [12]CPP is now commercially available from Tokyo Chemical Industry Co., Ltd (TCI), catalog no. C2449.
31. 60 by [10]cycloparaphenylene: Formation of the shortest fullerene-peapod Angew. Chem., Int. Ed. 2011, 50, 8342-8344
32. Scott, L. T.; Jackson, E. A.; Zhang, Q.; Steinberg, B. D.; Bancu, M.; Li, B. A short, rigid, structurally pure carbon nanotube by stepwise chemical synthesis J. Am. Chem. Soc. 2012, 134, 107-110
33. Hitosugi, S.; Nakanishi, W.; Yamasaki, T.; Isobe., H. Bottom-up synthesis of finite models of helical (n,m)-single-wall carbon nanotubes Nat. Commun. 2011, 2, 492
34. Kawase, T.; Kurata, H. Ball-, bowl-, and belt-shaped conjugated systems and their complexing abilities: Exploration of the concave-convex π-π Interaction Chem. Rev. 2006, 106, 5250-5273
35. Tahara, K.; Tobe, Y. Molecular loops and belts Chem. Rev. 2006, 106, 5274-5290
36. Parekh, V. C.; Guha, P. C. Synthesis of p,p′-diphenylene disulfide J. Indian Chem. Soc. 1934, 11, 95-100
37. Friederich, R.; Nieger, M.; Vögtle, F. Auf dem weg zu makrocyclischen para -phenylenen Chem. Ber. 1993, 126, 1723-1732
38. n]paracyclophanes J. Mol. Model. 2000, 6, 226-233
39. Basu, S.; Ghosh, P.; Mandal, B. Algorithms to calculate the distance numbers and the wiener indices of linear and cylindrical poly(p -phenylene) in terms of number of hexagonal rings Mol. Phys. 2008, 106, 2507-2513
40. Wong, B. M. Optoelectronic properties of carbon nanorings: excitonic effects from time-dependent J. Phys. Chem. C 2009, 113, 21921-21927
41. Viavattene, R. L.; Greene, F. D.; Cheung, L. D.; Majeste, R.; Trefonas, L. M. 9,9′,10,10′-Tetradehydrodianthracene. Formation, protection, and regeneration of a strained double bond J. Am. Chem. Soc. 1974, 96, 4342-4343
42. Kammermeier, S.; Herges, R. Photochemically induced metathesis reactions of tetradehydrodianthracene: Synthesis and structure of bianthraquinodimethanes Angew. Chem., Int. Ed. Engl. 1996, 35, 417-419
43. Kammermeier, S.; Jones, P. G.; Herges, R. Beltlike aromatic hydrocarbons by metathesis reaction with tetradehydrodianthracene Angew. Chem., Int. Ed. Engl. 1997, 36, 2200-2202
44. Ishiyama, T.; Murata, M.; Miyaura, N. Palladium(0)-catalyzed cross-coupling reaction of alkoxydiboron with haloarenes: A direct procedure for arylboronic esters J. Org. Chem. 1995, 60, 7508-7510
45. Miyaura, N.; Suzuki, A. Palladium-catalyzed cross-coupling reactions of organoboron compounds Chem. Rev. 1995, 95, 2457-2483
46. Billingsley, K. L.; Anderson, K. W.; Buchwald, S. L. A highly active catalyst for Suzuki-Miyaura cross-coupling reactions of heteroaryl compounds Angew. Chem., Int. Ed. 2006, 45, 3484-3488
47. Martin, R.; Buchwald, S. L. Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions employing dialkylbiaryl phosphine ligands Acc. Chem. Res. 2008, 41, 1461-1473
48. Imamoto, T. Carbonyl Addition Reactions Promoted by Cerium Reagents Pure Appl. Chem. 1990, 62, 747-752
49. Billingsley, K. L.; Barder, T. E.; Buchwald, S. L. Palladium-catalyzed borylation of aryl chlorides: Scope, applications, and computational studies Angew. Chem., Int. Ed. 2007, 46, 5359-5363
50. Nelson, T. D.; Crouch, R. D. Cu, Ni, and Pd mediated homocoupling reactions in biaryl syntheses: The Ullmann reaction Org. React. 2004, 63, 265
51. Tsou, T. T.; Kochi, J. K. Mechanism of biaryl synthesis with nickel complexes J. Am. Chem. Soc. 1979, 101, 7547-7560
52. Yamamoto, T.; Ito, T.; Kubota, K. A soluble poly(arylene) with large degree of depolarization. Poly(2,5-pyridinediyl) prepared by dehalogenation polycondensation of 2,5-dibromopyridine with Ni(0)-complexes Chem. Lett. 1988, 17, 153-154