Functionalized coronenes: Synthesis, solid structure, and properties

Journal of Organic Chemistry

Volumn 77, Issue 24, 2012, Pages 11319-11324

  Wu, Di ^a   Zhang, Hua ^a   Liang, Jinhua ^a   Ge, Haojie ^a   Chi, Chunyan ^b   Wu, Jishan ^b   Liu, Sheng Hua ^a   Yin, Jun ^a  

^a CENTRAL CHINA NORMAL UNIVERSITY   (China)

^b NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

BUILDING BLOCKES; FUNCTIONALIZED; OPTOELECTRONIC PROPERTIES; ORGANIC DEVICES; PACKING MOTIFS; PHOTO-STABILITY; SOLID STRUCTURES; TRIPHENYLENES;

CHEMISTRY;

ORGANIC COMPOUNDS;

CORONENE;

ARTICLE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CYCLIZATION; PHYSICAL CHEMISTRY; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

CHEMISTRY TECHNIQUES, SYNTHETIC; MODELS, MOLECULAR; MOLECULAR CONFORMATION; POLYCYCLIC COMPOUNDS; QUANTUM THEORY;

EID: 84871596154     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo302093t     Document Type: Article

References (53)

1. Novoselov, K. S.; Geim, A. K.; Morozov, S. V.; Jiang, D.; Zhang, Y.; Dubonos, S. V.; Grigorieva, I. V.; Firsov, A. A. Science 2004, 306, 666
2. Wu, J. Curr. Org. Chem. 2007, 11, 1220
3. Pisula, W.; Feng, X.; Müllen, K. Chem. Mater. 2011, 23, 554
4. Meng, Q.; Dong, H.; Hu, W.; Zhu, D. J. Mater. Chem. 2011, 21, 11708
5. Hill, J. P.; Jin, W.; Kosaka, A.; Fukushima, T.; Ichihara, H.; Shimomura, T.; Ito, K.; Hashizume, T.; Ishii, N.; Aida, T. Science 2004, 304, 1481
6. Simpson, C. D.; Wu, J.; Watson, M. D.; Müllen, K. J. Mater. Chem. 2004, 14, 494
7. Grimsdale, A. C.; Wu, J.; Müllen, K. Chem. Commun. 2005, 2197
8. Sergeyev, S.; Pisula, W.; Geerts, Y. H. Chem. Soc. Rev. 2007, 36, 1902
9. Pisula, W.; Feng, X.; Müllen, K. Adv. Mater. 2010, 22, 3634
10. Wu, J.; Pisula, W.; Müllen, K. Chem. Rev. 2007, 107, 718
11. Fetzer, J. C. The Chemistry and Analysis of the Large Polycyclic Aromatic Hydrocarbons; Wiley: New York, 2000.
12. Rieger, R.; Kastler, M.; Enkelmann, V.; Müllen, K. Chem.-Eur. J. 2008, 14, 6322
13. Rohr, U.; Schlichting, P.; Böhm, A.; Gross, M.; Meerholz, K.; Bräuchle, C.; Müllen, K. Angew. Chem. 1998, 110, 1463
14. Chi, X.; Besnard, C.; Thorsmolle, V. K.; Butko, V. Y.; Taylor, A. J.; Siegrist, T.; Ramirez, A. P. Chem. Mater. 2004, 16, 5751
15. Nolde, F.; Pisula, W.; Müller, S.; Kohl, C.; Müller, K. Chem. Mater. 2006, 18, 3715
16. Alibert-Fouet, S.; Seguy, I.; Bobo, J. -F.; Destruel, P.; Bock, H. Chem.-Eur. J. 2007, 13, 1746
17. An, Z.; Yu, J.; Domercq, B.; Jones, S. C.; Barlow, S.; Kippelen, B.; Marder, S. R. J. Mater. Chem. 2009, 19, 6688
18. Jia, H. P.; Liu, S. X.; Sanguinet, L.; Levillain, E.; Decurtins, S. J. Org. Chem. 2009, 74, 5727
19. Ghosh, A.; Rao, K. V.; George, S. J.; Rao, C. N. R. Chem.-Eur. J. 2010, 16, 2700
20. Newma, M. S. J. Am. Chem. Soc. 1940, 62, 1683
21. Baker, W.; Glockling, F.; Mcomie, J. F. W. J. Chem. Soc. 1951, 1118
22. Clar, E.; Zander, M. J. Chem. Soc. 1957, 4616
23. Craig, J. T.; Halton, B.; Lo, S.-F. Aust. J. Chem. 1975, 28, 913
24. Jessup, P. J.; Reiss, J. A. Aust. J. Chem. 1977, 30, 843
25. Dijk, J. T. M.; Van; Hartwijk, A.; Bleeker, A. C.; Lugtenburg, J.; Cornelisse, J. J. Org. Chem. 1996, 61, 1136
26. Shen, H. -C.; Tang, J. -M.; Chang, H. -K.; Yang, C. -W.; Liu, R. -S. J. Org. Chem. 2005, 70, 10113
27. Langhals, H.; Grundner, S. Chem. Ber. 1986, 119, 2373
28. Yang, B.; Li, Y.; Xie, M. G. Chin. Chem. Lett. 2003, 14, 783
29. Rao, K. V.; George, S. J. Org. Lett. 2010, 12, 2656
30. Franceschin, M.; Alvino, A.; Ortaggi, G.; Bianco, A. Tetrahedron Lett. 2004, 45, 9015
31. Franceschin, M.; Alvino, A.; Casagrande, V.; Mauriello, C.; Pascucci, E.; Savino, M.; Ortaggia, G.; Bianco, A. Bioorg. Med. Chem. 2007, 15, 1848
32. Lee, I. H.; Jeon, Y. M.; Gong, M. -S. Synth. Met. 2008, 158, 532
33. Yan, Q.; Cai, K.; Zhang, C.; Zhao, D. Org. Lett. 2012, 14, 4654
34. Pérez, D.; Guitián, E. Chem. Soc. Rev. 2004, 33, 274
35. Mamane, V.; Hannen, P.; Fürstner, A. Chem.-Eur. J. 2004, 10, 4556
36. Storch, J.; Čermák, J.; Karban, J. Tetrahedron Lett. 2007, 48, 6814
37. Xie, C.; Zhang, Y.; Yang, Y. Chem. Commun. 2008, 4810
38. Chen, T.-A.; Lee, T.-J.; Lin, M.-Y.; Sohel, S. M. A.; Diau, E. W.-G.; Lush, S.-F.; Liu, R.-S. Chem.-Eur. J. 2010, 16, 1826
39. Walker, D. B.; Howgego, J.; Davis, A. O. Synthesis 2010, 3686
40. Matsuda, T.; Moriya, T.; Goya, T.; Murakami, M. Chem. Lett. 2011, 40, 40
41. Shaibu, B. S.; Lin, S.-H.; Lin, C.-Y.; Wong, K.-T.; Liu, R.-S. J. Org. Chem. 2011, 76, 1054
42. Yao, T.; Campo, M. A.; Larock, R. C. Org. Lett. 2004, 6, 2677
43. Yao, T.; Campo, M. A.; Larock, R. C. J. Org. Chem. 2005, 70, 3511
44. Li, C.-W.; Wang, C.-I; Liao, H.-Y.; Chaudhuri, R.; Liu, R.-S. J. Org. Chem. 2007, 72, 9203
45. Mukherjee, A.; Pati, K.; Liu, R.-S. J. Org. Chem. 2009, 74, 6311
46. Li, Z.; Zhi, L.; Lucas, N. T.; Wang, Z. Tetrahedron 2009, 65, 3417
47. Andresen, T. L.; Krebs, F. C.; Thorup, N.; Bechgaard, K. Chem. Mater. 2000, 12, 2428
48. Zyss, J.; Ledoux-Rak, I.; Weiss, H. -C.; Bläser, D.; Boese, R.; Thallapally, P. K.; Thalladi, V. R.; Desiraju, G. R. Chem. Mater. 2003, 15, 3063
49. Wang, Y.; Stretton, A. D.; McConnell, M. C.; Wood, P. A.; Parsons, S.; Henry, J. B; Mount, A. R.; Galow, T. H. J. Am. Chem. Soc. 2007, 129, 13193
50. Tauer, T. P.; Derrick, M. E.; Sherrill, C. D. J. Phys. Chem. A. 2005, 109, 191
51. Jiang, L.; Dong, H.; Hu, W. J. Mater. Chem. 2010, 20, 4994
52. Scholl, R.; Meyer, K. Ber. Dtsch. Chem. Ges. 1932, 65, 902
53. Chi, C.; Wegner, G. Macromol. Rapid Commun. 2005, 26, 1532