Core-tetrasubstituted naphthalene diimides: Synthesis, optical properties, and redox characteristics

Journal of Organic Chemistry

Volumn 72, Issue 21, 2007, Pages 8070-8075

  Röger, Cornelia ^a   Würthner, Frank ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINATION; DIBROMOISOCYANURIC ACID; NAPHTHALENE DIIMIDE (NDI); NUCLEOPHILIC SUBSTITUTION;

CHROMOPHORES; CYCLIC VOLTAMMETRY; ELECTROCHEMICAL PROPERTIES; FLUORESCENCE SPECTROSCOPY; OPTICAL PROPERTIES; REDOX REACTIONS; SYNTHESIS (CHEMICAL);

NAPHTHALENE;

2,3,6,7 TETRABROMONAPHTHALENE DIANHYDRIDE; 2,6 DIISOPROPYLANILINE; ACID ANHYDRIDE; ALKYL GROUP; ANILINE DERIVATIVE; BROMINE DERIVATIVE; CYANURIC ACID; FUNCTIONAL GROUP; IMIDE; NAPHTHALENE DERIVATIVE; UNCLASSIFIED DRUG;

ABSORPTION; ARTICLE; BROMINATION; CHEMICAL REACTION; CHROMATOPHORE; CYCLIC POTENTIOMETRY; ELECTROCHEMICAL ANALYSIS; FLUORESCENCE SPECTROSCOPY; OPTICS; OXIDATION REDUCTION REACTION; QUANTUM YIELD; REACTION ANALYSIS; SYNTHESIS; ULTRAVIOLET RADIATION;

EID: 35348845160     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo7015357     Document Type: Article

References (46)

1. (a) Katz, H. E.; Lovinger, A. J.; Johnson, J.; Kloc, C.; Siegrist, T.; Li, W.; Lin, Y.-Y.; Dodabalapur, A. Nature 2000, 404, 478-481.
2. (b) Katz, H. E.; Johnson, J.; Lovinger, A. J.; Li, W. J. Am. Chem. Soc. 2000, 122, 7787-7792.
3. (c) Würthner, F. Angew. Chem. 2001, 113, 1069-1071;
4. Angew. Chem., Int. Ed. 2001, 40, 1037-1039.
5. (d) Hizu, K.; Sekitani, T.; Someya, T.; Otsuki, J. Appl. Phys. Lett. 2007, 90, 093504.
6. (a) Hasharoni, K.; Levanon, H.; Greenfield, S. R.; Gosztola, D. J.; Svec, W. A.; Wasielewski, M. R. J. Am. Chem. Soc. 1995, 117, 8055-8056.
7. (b) Greenfield, S. R.; Svec, W. A.; Gosztola, D.; Wasielewski, M. R. J. Am. Chem. Soc. 1996, 118, 6767-6777.
8. (c) Levanon, H.; Galili, T.; Regev, A.; Wiederrecht, G. P.; Svec, W. A.; Wasielewski, M. R. J. Am. Chem. Soc. 1998, 120, 6366-6373.
9. (d) Lukas, A. S.; Bushard, P.; Wasielewski, M. R. J. Phys. Chem. A 2002, 106, 2074-2082.
10. (e) Kelley, R. F.; Tauber, M. J.; Wasielewski, M. R. J. Am. Chem. Soc. 2006, 128, 4779-4791.
11. (f) Wasielewski, M. R. J. Org. Chem. 2006, 71, 5051-5066.
12. (g) Flamingi, L.; Baranoff, E.; Collin, J.-P.; Sauvage, J.-P. Chem. Eur. J. 2006, 12, 6592-6606.
13. (a) Hamilton, D. G.; Montalti, M.; Prodi, L.; Fontani, M.; Zanello, P.; Sanders, J. K. M. Chem. Eur. J. 2000, 6, 608-617.
14. (b) Kaiser, G.; Jarrosson, T.; Otto, S.; Ng, Y.-F.; Bond, A. D.; Sanders, J. K. M. Angew. Chem. 2004, 116, 1993-1996;
15. Angew. Chem., Int. Ed. 2004, 43, 1959-1962.
16. (c) Iijima, T.; Vignon, S. A.; Tseng, H.-R.; Jarrosson, T.; Sanders, J. K. M.; Marchioni, F.; Venturi, M.; Apostoli, E.; Balzani, V.; Stoddart, J. F. Chem. Eur. J. 2004, 10, 6375-6392.
17. (d) Johnstone, K. D.; Bampos, N.; Sanders, J. K. M.; Gunter, M. J. New J. Chem. 2006, 30, 861-867.
18. Lavin, J. M.; Shimizu, K. D. Chem. Commun. 2007, 228-230.
19. Lee, H. N.; Xu, Z.; Kim, S. K.; Swamy, K. M. K.; Kim, Y.; Kim, S.-J.; Yoon, J. J. Am. Chem. Soc. 2007, 129, 3828-3829.
20. (a) Takenaga, S.; Uto, Y.; Saita, H.; Yokoyama, M.; Kondo, H.; Wilson, W. D. Chem. Commun. 1998, 1111-1112.
21. (b) Guelev, V.; Sorey, S.; Hoffman, D. W.; Iverson, B. L. J. Am. Chem. Soc. 2002, 124, 2864-2865.
22. (c) Gui, E.-L.; Li, L.-J.; Lee, P. S.; Lohani, A.; Mhaisalkar, S. G.; Cao, Q.; Kang, S. J.; Rogers, J. A.; Tansil, N. C.; Gao, Z. Appl. Phys. Lett. 2006, 89, 232104.
23. (a) Pantos, G. D.; Pengo, P.; Sanders, J. K. M. Angew. Chem. 2007, 119, 198-201;
24. Angew. Chem., Int. Ed. 2007, 46, 194-197.
25. (b) Pantos, G. D.; Wietor, J.-L.; Sanders, J. K. M. Angew. Chem. 2007, 119, 2288-2290;
26. Angew. Chem., Int. Ed. 2007, 46, 2238-2240.
27. (a) Talukdar, P.; Bollot, G.; Mareda, J.; Sakai, N.; Matile, S. J. Am. Chem. Soc. 2005, 127, 6528-6529.
28. (b) Talukdar, P.; Bollot, G.; Mareda, J.; Sakai, N.; Matile, S. Chem. Eur. J. 2005, 11, 6525-6532.
29. Gorteau, V.; Bollot, G.; Mareda, J.; Perez-Velasco, A.; Matile, S. J. Am. Chem. Soc. 2006, 128, 14788-14789.
30. Mukhopadhyay, P.; Iwashita, Y.; Shirakawa, M.; Kawano, S.; Fujita, N.; Shinkai, S. Angew. Chem. 2006, 118, 1622-1625;
31. Angew. Chem., Int. Ed. 2006, 45, 1592-1595.
32. Ghosh, S.; Ramakrishnan, S. Angew. Chem. 2005, 117, 5577-5583;
33. Angew. Chem., Int. Ed. 2005, 44, 5441-5447.
34. (a) Würthner, F.; Ahmed, S.; Thalacker, C.; Debaerdemaeker, T. Chem. Eur. J. 2002, 8, 4742-4750.
35. (b) Thalacker, C.; Miura, A.; De Feyter, S.; De Schryver, F. C.; Würthner, F. Org. Biomol. Chem. 2005, 3, 414-422.
36. (c) Thalacker, C.; Röger, C.; Würthner, F. J. Org. Chem. 2006, 71, 8098-8105.
37. Röger, C.; Müller. M. G.; Lysetska, M.; Miloslavina, Y.; Holzwarth, A. R.; Würthner, F. J. Am. Chem. Soc. 2006, 128, 6542-6543.
38. Bhosale, S.; Sisson, A. L.; Talukdar, P.; Fürstenberg, A.; Banerji, N.; Vauthey, E.; Bollot, G.; Mareda, J.; Röger, C.; Würthner, F.; Sakai, N.; Matile, S. Science 2006, 313, 84-86.
39. Blaszczyk, A.; Fischer, M.; von Hänisch, C.; Mayor, M. Helv. Chim. Acta 2006, 89, 1986-2005.
40. Jones, B. A.; Facchetti, A.; Marks, T. J.; Wasielewski, M. R. Chem. Mater. 2007, 19, 2703-2705.
41. Roger, C.; Ahmed, S.; Würthner, F. Synthesis 2007, 1872-1876.
42. Vollmann, H.; Becker, H.; Corell, M.; Streeck, H. Justus Liebigs Ann. 1937, 531, 1-159.
43. Chaignon, F.; Falkenström, M.; Karlsson, S.; Blart, E.; Odobel, F.; Hammarström, L. Chem. Commun. 2007, 64-66.
44. Solomatin, G. G.; Filippov, M. P.; Shigalevskii, V. A. Zh. Org. Khim. 1981, 17, 877-879.
45. Könemann, M. (BASF AG), PCT Int. Appl. WO 2007074137A1, 2007. This patent was disclosed on July 5th, 2007 and describes the synthesis of tetrabromo- and tetracyano-substituted naphthalene dianhydrides and diimides and their application as n-type organic semiconductors.
46. Zaumseil, J.; Sirringhaus, H. Chem. Rev. 2007, 107, 1296-1323.