Synthesis of methoxy-substituted picenes: Substitution position effect on their electronic and single-crystal structures

Journal of Organic Chemistry

Volumn 79, Issue 11, 2014, Pages 4973-4983

  Mori, Hiroki ^a   Chen, Xi Chao ^a   Chang, Ning Hui ^a   Hamao, Shino ^a   Kubozono, Yoshihiro ^a,b   Nakajima, Kiyohiko ^c   Nishihara, Yasushi ^a,b  

^a OKAYAMA UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^c AICHI UNIVERSITY OF EDUCATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIZATION; ELECTRONIC STRUCTURE;

PACKING STRUCTURE; PHYSICOCHEMICAL PROPERTY; SINGLE-CRYSTAL STRUCTURE; STACKED STRUCTURE; STERIC HINDRANCES; SUZUKI-MIYAURA COUPLING; TRANSFER INTEGRAL; WITTIG REACTION;

SINGLE CRYSTALS;

AROMATIC COMPOUND; PICENE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; CYCLIZATION; ELECTRONICS; PHYSICAL CHEMISTRY; SUZUKI REACTION; SYNTHESIS; WITTIG REACTION;

EID: 84902105390     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo500543h     Document Type: Article

References (48)

1. Forrest, S. R.; Thompson, M. E. Chem. Rev. 2007, 107, 923
2. Wu, J.; Pisula, W.; Müllen, K. Chem. Rev. 2007, 107, 718
3. Koch, N. ChemPhysChem 2007, 8, 1438
4. Pron, A.; Gawrys, P.; Zagorska, M.; Djuradoa, D.; Demadrille, R. Chem. Soc. Rev. 2010, 39, 2577
5. Kelley, T. W.; Muyres, D. V.; Baude, P. F.; Smith, T. P.; Jones, T. D. Mater. Res. Soc. Symp. Proc. 2003, 771, 169
6. Ruiz, R.; Choudhary, D.; Nickel, B.; Toccoli, T.; Chang, K.-C.; Mayer, A. C.; Clancy, P.; Blakely, J. M.; Headrick, R. L.; Iannotta, S.; Malliaras, G. G. Chem. Mater. 2004, 16, 4497
7. Katz, H. E. Chem. Mater. 2004, 16, 4748
8. Anthony, J. E. Chem. Rev. 2006, 106, 5028
9. Anthony, J. E. Angew. Chem., Int. Ed. 2008, 47, 452
10. Hasegawa, T.; Takeya, J. Sci. Technol. Adv. Mater. 2009, 10, 024314
11. Klauk, H.; Zschieschang, U.; Weitz, R. T.; Meng, H.; Sun, F.; Nunes, G.; Keys, D. E.; Fincher, C. R.; Xiang, Z. Adv. Mater. 2007, 19, 3882
12. Maliakal, A.; Raghavachari, K.; Katz, H.; Chandross, E.; Siegrist, T. Chem. Mater. 2004, 16, 4980
13. Coppo, P.; Yeates, S. G. Adv. Mater. 2005, 17, 3001
14. Okamoto, H.; Kawasaki, N.; Kaji, Y.; Kubozono, Y.; Fujiwara, A.; Yamaji, M. J. Am. Chem. Soc. 2008, 130, 10470
15. Kawasaki, N.; Kubozono, Y.; Okamoto, H.; Fujiwara, A.; Yamaji, M. Appl. Phys. Lett. 2009, 94, 043310
16. Wang, Y.; Motta, S. D.; Negri, F.; Friedlein, R. J. Am. Chem. Soc. 2011, 133, 10054
17. Mitsuhashi, R.; Suzuki, Y.; Yamanari, Y.; Mitamura, H.; Kambe, T.; Ikeda, N.; Okamoto, H.; Fujiwara, A.; Yamaji, M.; Kawasaki, N.; Maniwa, Y.; Kubozono, Y. Nature 2010, 464, 76
18. Review: Kubozono, Y.; Mitamura, H.; Lee, X.; He, X.; Yamanari, Y.; Takahashi, Y.; Suzuki, Y.; Kaji, Y.; Eguchi, R.; Akaike, K.; Kambe, T.; Okamoto, H.; Fujiwara, A.; Kato, T.; Kosugi, T.; Aoki, H. Phys. Chem. Chem. Phys. 2011, 13, 16476
19. Chang, N. H.; Chen, X. C.; Nonobe, H.; Okuda, Y.; Mori, H.; Nakajima, K.; Nishihara, Y. Org. Lett. 2013, 15, 3558
20. Echavareen, A. M.; Gómez-Lor, B.; González, J. J.; Frutos, Ȯ. D. Synlett 2003, 585
21. Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174
22. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
23. Wang, L.; Shevlin, P. B. Org. Lett. 2000, 2, 3703
24. Marcinow, Z.; Sygula, A.; Ellern, A.; Rabideau, P. W. Org. Lett. 2001, 3, 3527
25. Campeau, L. C.; Parisien, M.; Jean, A.; Fagnou, K. J. Am. Chen. Soc. 2006, 128, 581
26. Chang, H. I.; Huang, H. T.; Huang, C. H.; Kuo, M. Y.; Wu, Y. T. Chem. Commun. 2010, 46, 7241
27. Tsuji, H.; Ueda, Y.; Ilies, L.; Nakamura, E. J. Am. Chem. Soc. 2010, 132, 11854
28. Peng, J. S.; Chen, T. H.; Chen, C. X.; Li, B. J. Org. Chem. 2011, 76, 9507
29. The Wittig reactions were carried out according to the literature procedures; for an example see: Dunne, E. C.; Coyne, é. J.; Crowley, P. B.; Gilheany, D. G. Tetrahedron Lett. 2002, 43, 2449
30. Fanetti, S.; Citroni, M.; Bini, R.; Malavasi, L.; Artioli, G. A.; Postorino, P. J. Chem. Phys. 2012, 137, 224506
31. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, N. J.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision A.02, Gaussian, Inc., Wallingford, CT, 2009.
32. Osaka, I.; Shinamura, S.; Abe, T.; Takimiya, K. J. Mater. Chem. C 2013, 1, 1297
33. Brédas, J. L.; Beljonne, D.; Coropceanu, V.; Cornil, J. Chem. Rev. 2004, 104, 4971
34. Sakanoue, K.; Motoda, M.; Sugimoto, M.; Sakaki, S. J. Phys. Chem. A 1999, 103, 5551
35. Salman, S.; Delgado, M. C. R.; Coropceanu, V.; Brédas, J. L. Chem. Mater. 2009, 21, 3593
36. Saranya, G.; Navamani, K.; Senthikumar, K. Chem. Phys. 2014, 433, 48
37. Torii, S. Electroorganic syntheses: methods and applications; VCH: Weinheim, Germany, 1985; Part 1 (Oxidations).
38. ADF 2013.01: powerful DFT code for modeling molecules; Scientific Computing and Modeling, Amsterdam; http://www.scm.com/ADF/.
39. Senthilkumar, K.; Grozema, F. C.; Bickelhaupt, F. M.; Siebbeles, L. D. A. J. Chem. Phys. 2003, 119, 9808
40. Prins, P.; Senthilkumar, K.; Grozema, F. C.; Jonkheijm, P.; Schenning, A. P. H. J.; Meijer, E. W.; Siebbeles, L. D. A. J. Phys. Chem. B 2005, 109, 18267
41. De, A.; Ghosh, R.; Roychowdhury, S.; Roychowdhury, P. Acta Crystallogr., Sect. C 1985, C41, 907
42. Takimiya, K.; Shinamura, S.; Osaka, I.; Miyazaki, E. Adv. Mater. 2011, 23, 4347
43. Kang, M. J.; Yamamoto, T.; Shinamura, S.; Miyazaki, E.; Takimiya, K. Chem. Sci. 2010, 1, 179
44. Stewart, S. K.; Whiting, A. J. Organomet. Chem. 1994, 482, 293
45. Kiesewetter, E. T.; OBrien, R. V.; Yu, E. C.; Meek, S. J.; Schrock, R. R.; Hoveyda, A. H. J. Am. Soc. Chem. 2013, 135, 6026
46. Nakayama, J.; Sakai, A.; Hoshino, M. J. Org. Chem. 1984, 49, 5084
47. Mello, J. V.; Finney, N. S. J. Am. Chem. Soc. 2005, 127, 10124
48. Kamikawa, K.; Takemoto, I.; Takemoto, S.; Matsuzaka, H. J. Org. Chem. 2007, 72, 7406