Heterocyclic annelated di(perylene bisimide): Constructing bowl-shaped perylene bisimides by the combination of steric congestion and ring strain

Journal of Organic Chemistry

Volumn 74, Issue 16, 2009, Pages 6275-6282

  Qian, Hualei ^a,d   Yue, Wan ^a,d   Zhen, Yonggang ^a,d   Di Motta, Simone ^b,c   Di Donato, Eugenio ^b,c   Negri, Fabrizia ^b,c   Qu, Jianqiang ^e   Xu, Wei ^a   Zhu, Daoben ^a   Wang, Zhaohui ^a  

^a INSTITUTE OF CHEMISTRY   (China)

^b UNIVERSITY OF BOLOGNA   (Italy)

^c INSTM   (Italy)

^d UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

^e BASF SE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ATOMIC STRUCTURE; CHEMICAL EQUATIONS; HETEROATOMS; N-HETEROCYCLIC; OPTICAL SIGNATURES; PERYLENE BISIMIDES; PYRAMIDALIZATION ANGLE; RING STRAINS; SINGLE CRYSTAL X-RAY STRUCTURES; SPECTROSCOPIC CHARACTERIZATION; STERIC CONGESTION; TEMPERATURE DEPENDENT;

ATOMIC SPECTROSCOPY; CHEMICAL REACTIONS; CURVE FITTING; ELECTROCHEMICAL PROPERTIES; ELECTRON TRANSITIONS; ELECTRONIC PROPERTIES; OPTICAL PROPERTIES;

DENSITY FUNCTIONAL THEORY;

HETEROCYCLIC COMPOUND; PERYLENE;

ARTICLE; CHEMICAL REACTION; CRYSTAL STRUCTURE; DENSITY FUNCTIONAL THEORY; ELECTROCHEMICAL ANALYSIS; GEOMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM CHEMISTRY; SPECTROSCOPY; STRUCTURE ANALYSIS; SYNTHESIS; X RAY ANALYSIS;

EID: 70349096406     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901285k     Document Type: Article

References (46)

1. (a) Rabideau, P. W.; Sygula, A. Acc. Chem. Res. 1996, 29, 235-242.
2. (b) Wu, Y.; Siegel, J. S. Chem. Rev. 2006, 106, 4843-4867.
3. (c) Tsefrikas, V. M.; Scott, L. T. Chem. Rev. 2006, 106, 4868-4884.
4. (d) Kawase, T.; Kurata, H. Chem. Rev. 2006, 106, 5250-5273.
5. (a) Scott, L. T.; Boorum, M. M.; Mcmahon, B. J.; Hagen, S.; Mack, J.; Blank, J.; Wegner, H.; Meijere, A. D. Science 2002, 295, 1500-1503.
6. (b) Bronstein, H. E.; Choi, N.; Scott, L. T. J. Am. Chem. Soc. 2002, 124, 8870-8875.
7. (a) Sygula, A.; Rabideau, P. W. J. Am. Chem. Soc. 1999, 121, 7800-7803.
8. (b) Seiders, T. J.; Elliott, E. L.; Grube, G. H.; Siegel, J. S. J. Am. Chem. Soc. 1999, 121, 7804-7813.
9. (c) Sakurai, H.; Daiko, T.; Hirao, T. Science 2003, 301, 1878.
10. (a) Bendikov, M.; Wudl, F. Chem. Rev. 2004, 104, 4891-4945.
11. (b) Anthony, J. E. Chem. Rev. 2006, 106, 5028-5048.
12. (c) Wu, Y.; Li, Y.; Gardner, S.; Ong, B. S. J. Am. Chem. Soc. 2005, 127, 614-618.
13. (a) Imamura, K.; Takimiya, K.; Aso, Y.; Otsubo, T. Chem. Commun. 1999, 1859-1860.
14. (b) Mascal, M.; Lera, M.; Blake, A. J. J. Org. Chem. 2000, 65, 7253-7255.
15. (c) Mascal, M.; Bertran, J. C. J. Am. Chem. Soc. 2005, 127, 1352-1353.
16. (a) Herbst, W.; Hunger, K. Industrial Organic Pigments: Production, Properties, Applications, 2nd ed.; WILEY-VCH:Weinheim, Germany, 1997.
17. (b) Zollinger, H. Color Chemistry, 3rd ed.; VCH: Weinheim, Germany, 2003.
18. (a) Schmidt-Mende, L.; Fechtenkötter, A.; Müllen, K.; Moons, E.; Friend, R. H.; Mackenzie, J. D. Science 2001, 293, 1119-1122.
19. (b) Ego, C.; Marsitzky, D.; Becker, S.; Zhang, J.; Grimsdale, A. C.; Müllen, K.; Mackenzie, J. D.; Silva, C.; Friend, R. H. J. Am. Chem. Soc. 2003, 125, 437-443.
20. (c) Jones, B. A.; Ahrens, M. J.; Yoon, M.; Facchetti, A.; Marks, T. J.; Wasielewski, M. R. Angew. Chem., Int. Ed. 2004, 43, 6363-6366.
21. (d) Schmidt, R.; Ling, M. M.; Oh, J. H.; Winkler, M.; Könemann, M.; Bao, Z.; Würthner, F. Adv. Mater. 2007, 19, 3692-3695.
22. (a) Würthner, F. Chem. Commun. 2004, 1564-1579.
23. (b) Wasielewski, M. R. J. Org. Chem. 2006, 71, 5051-5066.
24. (c) Watson, M. D.; Fechtenkotter, A.; Müllen, K. Chem. Rev. 2001, 101, 1267-1300.
25. (a) Hadicke, E.; Graser, F. Acta Crystallogr., Sect. C 1986, 42, 189-195.
26. (b) Chen, Z.; Debije, M. G.; Debaerdemaeker, T.; Osswald, P.; Würthner, F. ChemPhysChem 2004, 5, 137-140.
27. (c) Osswald, P.; Leusser, D.; Stalke, D.; Würthner, F. Angew. Chem., Int. Ed. 2005, 44, 250-253.
28. (d) Shaller, A. D.; Wang, W.; Gan, H.; Li, A. D. Q. Angew. Chem., Int. Ed. 2008, 47, 7705-7709.
29. (e) Wang, W.; Shaller, A. D.; Li, A. D. Q. J. Am. Chem. Soc. 2008, 130, 8271-8279.
30. (f) Li, Y.; Tan, L.; Wang, Z.; Qian, H.; Shi, Y.; Hu, W. Org. Lett. 2008, 10, 529-532.
31. Qian, H.; Liu, C.; Wang, Z.; Zhu, D. Chem. Commun. 2006, 4587-4589.
32. Ackermann, L.; Althammer, A. Angew. Chem., Int. Ed. 2007, 46, 1627-1629.
33. Qian, H.; Wang, Z.; Yue, W.; Zhu, D. J. Am. Chem. Soc. 2007, 129, 10664-10665.
34. Qian, H.; Negri, F.; Wang, C.; Wang, Z. J. Am. Chem. Soc. 2008, 130, 17970-17976.
35. (a) Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100.
36. (b) Lee, C.; Yang, W.; Parr, G. G. Phys. Rev. B 1988, 37, 785-789.
37. Molekel, version 4.3, http://www.cscs.ch/molkel/;
38. Portmann, S.; Lüthi, H. P. Chimia 2000, 54, 766.
39. Frisch, M. J.; et al. Gaussian 03, revision C.02; Gaussian, Inc., Pittsburgh, PA, 2003.
40. (a) Kosugi, M.; Ogata, T.; Terada, M.; Sano, H.; Migita, T. Bull. Chem. Soc. Jpn. 1985, 58, 3657-3658.
41. (b) Zhang, X.; Côté, A. P.; Matzger, A. J. J. Am. Chem. Soc. 2005, 127, 10502-10503.
42. (a) Hartwig, J. F. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E. I., de Meijere, A., Eds.; Wiley-Interscience: Weinheim, Germany, 2002.
43. (b) Jiang, L.; Buchwald, S. L. In Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; de Meijere, A., Diederich, F., Eds.; John Wiely & Sons: Weinheim, Germany, 2004.
44. (a) Haddon, R. C.; Scott, L. T. Pure Appl. Chem. 1986, 58, 137-142.
45. (b) Haddon, R. C. J. Am. Chem. Soc. 1987, 109, 1676-1685.
46. (c) Haddon, R. C. Science 1993, 261, 1545-1550.