Octafunctionalized biphenylenes: Molecular precursors for isomeric graphene nanostructures

Angewandte Chemie - International Edition

Volumn 53, Issue 6, 2014, Pages 1538-1542

  Schlütter, Florian ^a   Nishiuchi, Tomohiko ^a   Enkelmann, Volker ^a   Müllen, Klaus ^a  

^a MAX PLANCK INSTITUTE FOR POLYMER RESEARCH   (Germany)

Author keywords

biphenylene; graphene; organic electronics; polycylic compounds

Indexed keywords

BIPHENYLENE; CARBON ALLOTROPES; CYCLODEHYDROGENATION; GRAPHENE NANORIBBONS; MOLECULAR PRECURSOR; ORGANIC ELECTRONICS; POLYCYLIC COMPOUNDS; STRAIGHT-FORWARD METHOD;

AROMATIC COMPOUNDS; DEHYDROGENATION; NANORIBBONS;

GRAPHENE;

EID: 84893441545     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201309324     Document Type: Article

References (70)

1. F. Diederich, Y. Rubin, Angew. Chem. 1992, 104, 1123-1146
2. Angew. Chem. Int. Ed. Engl. 1992, 31, 1101-1123
3. H. R. Karfunkel, T. Dressler, J. Am. Chem. Soc. 1992, 114, 2285-2288
4. M. D. Watson, A. Fechtenkötter, K. Müllen, Chem. Rev. 2001, 101, 1267-1300
5. F. Diederich, M. Kivala, Adv. Mater. 2010, 22, 803-812
6. A. Hirsch, Nat. Mater. 2010, 9, 868-871
7. J. Cai, P. Ruffieux, R. Jaafar, M. Bieri, T. Braun, S. Blankenburg, M. Muoth, A. P. Seitsonen, M. Saleh, X. L. Feng, K. Müllen, R. Fasel, Nature 2010, 466, 470-473
8. K. Kawasumi, Q. Zhang, Y. Segawa, L. T. Scott, K. Itami, Nat. Chem. 2013, 5, 739-744
9. Q. Song, B. Wang, K. Deng, X. L. Feng, M. Wagner, J. D. Gale, K. Müllen, L. J. Zhi, J. Mater. Chem. C 2013, 1, 38-41
10. L. Chen, Y. Hernandez, X. L. Feng, K. Müllen, Angew. Chem. 2012, 124, 7758-7773
11. Angew. Chem. Int. Ed. 2012, 51, 7640-7654.
12. H. W. Kroto, J. R. Heath, S. C. Obrien, R. F. Curl, R. E. Smalley, Nature 1985, 318, 162-163.
13. S. Iijima, Nature 1991, 354, 56-58.
14. K. S. Novoselov, A. K. Geim, S. V. Morozov, D. Jiang, Y. Zhang, S. V. Dubonos, I. V. Grigorieva, A. A. Firsov, Science 2004, 306, 666-669
15. A. K. Geim, K. S. Novoselov, Nat. Mater. 2007, 6, 183-191
16. A. K. Geim, Science 2009, 324, 1530-1534.
17. J. Gibson, M. Holohan, H. L. Riley, J. Chem. Soc. 1946, 456-461
18. A. Rajca, A. Safronov, S. Rajca, R. Shoemaker, Angew. Chem. 1997, 109, 504-507
19. Angew. Chem. Int. Ed. Engl. 1997, 36, 488-491
20. D. Wasserfallen, G. Mattersteig, V. Enkelmann, K. Müllen, Tetrahedron 2006, 62, 5417-5420
21. D. Türp, T. T. T. Nguyen, M. Baumgarten, K. Müllen, New J. Chem. 2012, 36, 282-298.
22. I. Meric, M. Y. Han, A. F. Young, B. Ozyilmaz, P. Kim, K. L. Shepard, Nat. Nanotechnol. 2008, 3, 654-659.
23. Z. B. Shifrina, M. S. Averina, A. L. Rusanov, M. Wagner, K. Müllen, Macromolecules 2000, 33, 3525-3529
24. M. Y. Han, B. Özyilmaz, Y. B. Zhang, P. Kim, Phys. Rev. Lett. 2007, 98, 206805
25. X. Y. Yang, X. Dou, A. Rouhanipour, L. J. Zhi, H. J. Räder, K. Müllen, J. Am. Chem. Soc. 2008, 130, 4216-4217
26. D. V. Kosynkin, A. L. Higginbotham, A. Sinitskii, J. R. Lomeda, A. Dimiev, B. K. Price, J. M. Tour, Nature 2009, 458, 872-875
27. A. Konishi, Y. Hirao, M. Nakano, A. Shimizu, E. Botek, B. Champagne, D. Shiomi, K. Sato, T. Takui, K. Matsumoto, H. Kurata, T. Kubo, J. Am. Chem. Soc. 2010, 132, 11021-11023
28. F. Schwierz, Nat. Nanotechnol. 2010, 5, 487-496
29. L. Dössel, L. Gherghel, X. L. Feng, K. Müllen, Angew. Chem. 2011, 123, 2588-2591
30. Angew. Chem. Int. Ed. 2011, 50, 2540-2543
31. M. G. Schwab, A. Narita, Y. Hernandez, T. Balandina, K. S. Mali, S. De Feyter, X. L. Feng, K. Müllen, J. Am. Chem. Soc. 2012, 134, 18169-18172
32. A. Konishi, Y. Hirao, K. Matsumoto, H. Kurata, R. Kishi, Y. Shigeta, M. Nakano, K. Tokunaga, K. Kamada, T. Kubo, J. Am. Chem. Soc. 2013, 135, 1430-1437
33. L. Talirz, H. Sode, J. M. Cai, P. Ruffieux, S. Blankenburg, R. Jafaar, R. Berger, X. Feng, K. Müllen, D. Passerone, R. Fasel, C. A. Pignedoli, J. Am. Chem. Soc. 2013, 135, 2060-2063
34. Z. Yan, Y. Liu, J. Lin, Z. Peng, G. Wang, E. Pembroke, H. Zhou, C. Xiang, A.-R. O. Raji, E. L. G. Samuel, T. Yu, B. I. Yakobson, J. M. Tour, J. Am. Chem. Soc. 2013, 135, 10755-10762.
35. C.-N. Feng, M.-Y. Kuo, Y.-T. Wu, Angew. Chem. 2013, 125, 7945-7948
36. Angew. Chem. Int. Ed. 2013, 52, 7791-7794
37. B. T. King, Nat. Chem. 2013, 5, 730-731
38. Y. Sakamoto, T. Suzuki, J. Am. Chem. Soc. 2013, 135, 14074-14077.
39. A. Rajca, A. Safronov, S. Rajca, C. R. Ross, J. J. Stezowski, J. Am. Chem. Soc. 1996, 118, 7272-7279.
40. B. C. Berris, G. H. Hovakeemian, Y. H. Lai, H. Mestdagh, K. P. C. Vollhardt, J. Am. Chem. Soc. 1985, 107, 5670-5687
41. H. Schwager, S. Spyroudis, K. P. C. Vollhardt, J. Organomet. Chem. 1990, 382, 191-200
42. R. H. Schmidt-Radde, K. P. C. Vollhardt, J. Am. Chem. Soc. 1992, 114, 9713-9715
43. K. P. C. Vollhardt, Pure Appl. Chem. 1993, 65, 153-156
44. D. Holmes, S. Kumaraswamy, A. J. Matzger, K. P. C. Vollhardt, Chem. Eur. J. 1999, 5, 3399-3412
45. O. Š. Miljanic̈, K. P. C. Vollhardt, Carbon-Rich Compounds, Wiley-VCH, Weinheim, 2006, pp. 140-197
46. M. J. Eichberg, K. N. Houk, J. Lehmann, P. W. Leonard, A. Marker, J. E. Norton, D. Sawicka, K. P. C. Vollhardt, G. D. Whitener, S. Wolff, Angew. Chem. 2007, 119, 7018-7022
47. Angew. Chem. Int. Ed. 2007, 46, 6894-6898.
48. H. Kidokoro, M. Sato, S. Ebine, Bull. Chem. Soc. Jpn. 1982, 55, 3204-3207
49. H. Kidokoro, Y. Saito, M. Sato, S. Ebine, S. Sato, T. Hata, C. Tamura, Bull. Chem. Soc. Jpn. 1983, 56, 1192-1195
50. M. K. Sheperd, Cyclobutarenes: The Chemistry of Benzocyclobutene, Biphenylene, and Related Compounds, Elsevier, New York, 1991.
51. V. Snieckus, Chem. Rev. 1990, 90, 879-933
52. F. Mongin, M. Schlosser, Tetrahedron Lett. 1997, 38, 1559-1562
53. M. Dabrowski, J. Kubicka, S. Luliński, J. Serwatowski, Tetrahedron Lett. 2005, 46, 4175-4178.
54. CCDC 954063 (5 c) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data request/cif.
55. Gaussian 03, Revision C.02, M. J. Frisch, et al., Gaussian, Inc., Wallingford CT, 2004 (see the Supporting Information for a full citation).
56. L. Zöphel, V. Enkelmann, R. Rieger, K. Müllen, Org. Lett. 2011, 13, 4506-4509.
57. CCDC 954062 (8 a) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
58. F. Ullmann, J. Bielecki, Ber. Dtsch. Chem. Ges. 1901, 34, 2174-2185
59. P. E. Fanta, Chem. Rev. 1946, 38, 139-196
60. P. E. Fanta, Synthesis 1974, 9-21
61. J. Hassan, M. Sevignon, C. Gozzi, E. Schulz, M. Lemaire, Chem. Rev. 2002, 102, 1359-1469.
62. R. Beck, S. A. Johnson, Chem. Commun. 2011, 47, 9233-9235.
63. A. C. Ferrari, J. C. Meyer, V. Scardaci, C. Casiraghi, M. Lazzeri, F. Mauri, S. Piscanec, D. Jiang, K. S. Novoselov, S. Roth, A. K. Geim, Phys. Rev. Lett. 2006, 97, 187401.
64. M. Kastler, J. Schmidt, W. Pisula, D. Sebastiani, K. Müllen, J. Am. Chem. Soc. 2006, 128, 9526-9534.
65. F. Schlütter, T. Nishiuchi, V. Enkelmann, K. Müllen, Polym. Chem. 2013, 4, 2963-2967.
66. CCDC 954064 (11 a) and 954065 (11 c) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif.
67. J. C. J. Bart, Acta Crystallogr. Sect. B 1968, 24, 1277-1287.
68. L. Y. Zhai, R. Shukla, R. Rathore, Org. Lett. 2009, 11, 3474-3477.
69. E. Clar, The Aromatic Sextet, Wiley, London, 1972
70. R. Rieger, K. Müllen, J. Phys. Org. Chem. 2010, 23, 315-325.