Regioselectivity in sequential nucleophilic substitution of tetrabromonaphthalene diimides

Journal of Organic Chemistry

Volumn 78, Issue 11, 2013, Pages 5227-5238

  Suraru, Sabin Lucian ^a   Würthner, Frank ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITIVES; ANILINE; DICHLOROMETHANE; ELECTRONIC PROPERTIES; FLUORINE COMPOUNDS; ISOMERS; NAPHTHALENE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION INTERMEDIATES;

NAPHTHALENE DIIMIDES; NUCLEOPHILIC SUBSTITUTIONS; REACTION CONDITIONS; REACTION SOLVENTS; REGIO-SELECTIVE; REGIOSELECTIVE SYNTHESIS; SEQUENTIAL REACTION; TETRABUTYLAMMONIUM FLUORIDES;

REGIOSELECTIVITY;

2,3 DIAMINO 6,7 DIBROMONAPHTHALENE DIIMIDE; 2,3,6,7 TETRABROMONAPHTHALENE DIIMIDE; 2,7 DIAMINO 3,6 DIBROMONAPHTHALENE DIIMIDE; AMINE; AMMONIUM DERIVATIVE; ANILINE; ANION; AROMATIC COMPOUND; CHLOROFORM; DIAMINO ACID; DICHLOROMETHANE; FLUORIDE ION; IMIDE; NAPHTHALENE DERIVATIVE; SOLVENT; TETRABUTYLAMMONIUM FLUORIDE; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; CHEMICAL MODIFICATION; CONTROLLED STUDY; DEPROTONATION; ISOMER; ISOMERIZATION; MOLECULAR ELECTRONICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEOPHILICITY; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 84879315367     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo400320a     Document Type: Article

References (43)

1. Bhosale, S. V.; Jani, C. H.; Langford, S. J. Chem. Soc. Rev. 2008, 37, 331-342
2. Sakai, N.; Mareda, J.; Vauthey, E.; Matile, S. Chem. Commun. 2010, 46, 4225-4237
3. Bhosale, S. V.; Bhosale, S. V.; Bhargava, S. K. Org. Biomol. Chem. 2012, 10, 6455-6468
4. Vollmann, H.; Becker, H.; Corell, M.; Streeck, H. Liebigs Ann. 1937, 531, 1-159
5. Thalacker, C.; Röger, C.; Würthner, F. J. Org. Chem. 2006, 71, 8098-8105
6. Röger, C.; Müller, M. G.; Lysetska, M.; Miloslavina, Y.; Holzwarth, A. R.; Würthner, F. J. Am. Chem. Soc. 2006, 128, 6542-6543
7. Röger, C.; Miloslavina, Y.; Brunner, D.; Holzwarth, A. R.; Würthner, F. J. Am. Chem. Soc. 2008, 130, 5929-5939
8. 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
9. Sakai, N.; Bhosale, R.; Emery, D.; Mareda, J.; Matile, S. J. Am. Chem. Soc. 2010, 132, 6923-6925
10. Sakai, N.; Lista, M.; Kel, O.; Sakurai, S.-i.; Emery, D.; Mareda, J.; Vauthey, E.; Matile, S. J. Am. Chem. Soc. 2011, 133, 15224-15227
11. Lista, M.; Areephong, J.; Sakai, N.; Matile, S. J. Am. Chem. Soc. 2011, 133, 15228-15231
12. Würthner, F.; Stolte, M. Chem. Commun. 2011, 47, 5109-5115
13. Zhan, X.; Facchetti, A.; Barlow, S.; Marks, T. J.; Ratner, M. A.; Wasielewski, M. R.; Marder, S. R. Adv. Mater. 2011, 23, 268-284
14. Gao, X.; Di, C.; Hu, Y.; Yang, X.; Fan, H.; Zhang, F.; Liu, Y.; Li, H.; Zhu, D. J. Am. Chem. Soc. 2010, 132, 3697-3699
15. Zhao, Y.; Di, C.; Gao, X.; Hu, Y.; Guo, Y.; Zhang, L.; Liu, Y.; Wang, J.; Hu, W.; Zhu, D. Adv. Mater. 2011, 23, 2448-2453
16. Suraru, S.-L.; Zschieschang, U.; Klauk, H.; Würthner, F. Chem. Commun. 2011, 47, 11504-11506
17. Polander, L. E.; Romanov, A. S.; Barlow, S.; Hwang, D. K.; Kippelen, B.; Timofeeva, T. V.; Marder, S. R. Org. Lett. 2012, 14, 918-921
18. Polander, L. E.; Tiwari, S. P.; Pandey, L.; Seifried, B. M.; Zhang, Q.; Barlow, S.; Risko, C.; Brédas, J.-L.; Kippelen, B.; Marder, S. R. Chem. Mater. 2011, 23, 3408-3410
19. Yan, H.; Chen, Z.; Zheng, Y.; Newman, C.; Quinn, J. R.; Dotz, F.; Kastler, M.; Facchetti, A. Nature 2009, 457, 679-686
20. Schubert, M.; Dolfen, D.; Frisch, J.; Roland, S.; Steyrleuthner, R.; Stiller, B.; Chen, Z.; Scherf, U.; Koch, N.; Facchetti, A.; Neher, D. Adv. Energy Mater. 2012, 2, 369-380
21. Würthner, F.; Ahmed, S.; Thalacker, C.; Debaerdemaeker, T. Chem.-Eur. J. 2002, 8, 4742-4750
22. Gao, X.; Qiu, W.; Yang, X.; Liu, Y.; Wang, Y.; Zhang, H.; Qi, T.; Liu, Y.; Lu, K.; Du, C.; Shuai, Z.; Yu, G.; Zhu, D. Org. Lett. 2007, 9, 3917-3920
23. Röger, C.; Würthner, F. J. Org. Chem. 2007, 72, 8070-8075
24. Fin, A.; Petkova, I.; Doval, D. A.; Sakai, N.; Vauthey, E.; Matile, S. Org. Biomol. Chem. 2011, 9, 8246-8252
25. Suraru, S.-L.; Würthner, F. Synthesis 2009, 11, 1841-1845
26. Ye, Q.; Chang, J.; Huang, K.-W.; Chi, C. Org. Lett. 2011, 13, 5960-5963
27. Krüger, H.; Janietz, S.; Sainova, D.; Dobreva, D.; Koch, N.; Vollmer, A. Adv. Funct. Mater. 2007, 17, 3715-3723
28. Hu, Y.; Gao, X.; Di, C.; Yang, X.; Zhang, F.; Liu, Y.; Li, H.; Zhu, D. Chem. Mater. 2011, 23, 1204-1215
29. Yue, W.; Gao, J.; Li, Y.; Jiang, W.; Di Motta, S.; Negri, F.; Wang, Z. J. Am. Chem. Soc. 2011, 133, 18054-18057
30. Cai, K.; Yan, Q.; Zhao, D. Chem. Sci. 2012, 3, 3175-3182
31. Li, C.; Xiao, C.; Li, Y.; Wang, Z. Org. Lett. 2013, 15, 682-685
32. Bhosale, S. V.; Bhosale, S. V.; Kalyankar, M. B.; Langford, S. J. Org. Lett. 2009, 11, 5418-5421
33. Chang, J.; Ye, Q.; Huang, K.-W.; Zhang, J.; Chen, Z.-K.; Wu, J.; Chi, C. Org. Lett. 2012, 14, 2964-2967
34. Guo, S.; Wu, W.; Guo, H.; Zhao, J. J. Org. Chem. 2012, 77, 3933-3943
35. Guha, S.; Saha, S. J. Am. Chem. Soc. 2010, 132, 17674-17677
36. Guha, S.; Goodson, F. S.; Corson, L. J.; Saha, S. J. Am. Chem. Soc. 2012, 134, 13679-13691
37. Aragay, G.; Frontera, A.; Lloveras, V.; Vidal-Gancedo, J.; Ballester, P. J. Am. Chem. Soc. 2013, 135, 2620-2627
38. Taft, R. W.; Bordwell, F. G. Acc. Chem. Res. 1988, 21, 463-469
39. Kennedy, A. R.; Klett, J.; O'Hara, C. T.; Mulvey, R. E.; Robertson, G. M. Eur. J. Inorg. Chem. 2009, 2009, 5029-5035
40. Gilchrist, T. L.; Gymer, G. E.; Rees, C. W. J. Chem. Soc., Chem. Commun. 1973, 835-836
41. Gilchrist, T. L.; Gymer, G. E.; Rees, C. W. J. Chem. Soc., Perkin Trans. 1975, 1, 1-8
42. Perrin, D. D.; Armarego, W. L. F.; Perrin, D. R. Purification of Laboratory Chemicals, 2 nd ed.; Pergamon Press, Ltd.: Oxford, 1980.
43. Fry, A. J. In Laboratory Techniques in Electroanalytical Chemistry, 2 nd ed.; Kissinger, P.; Heineman, W. R., Eds.; Marcel Dekker, Ltd.: New York, 1996.