Aromatic macrocycle containing amine and imine groups: Intramolecular charge-transfer and multiple redox behavior

Journal of Organic Chemistry

Volumn 76, Issue 22, 2011, Pages 9504-9506

  Ide, Tomohito ^a   Takeuchi, Daisuke ^a   Osakada, Kohtaro ^a   Sato, Takashi ^b   Higuchi, Masayoshi ^b  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b NATIONAL INSTITUTE FOR MATERIALS SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO GROUP; CHARGE TRANSFER TRANSITIONS; CYCLIC COMPOUNDS; DIIMINES; ELECTRON-RICH; INTRAMOLECULAR CHARGE TRANSFERS; MACROCYCLES; REDOX BEHAVIOR;

ANILINE; AROMATIC COMPOUNDS; CHARGE TRANSFER; KETONES;

CYCLIC VOLTAMMETRY;

AMINE; ANTHRAQUINONE; AROMATIC COMPOUND; BIS(4 AMINOPHENYL)AMINE; DIPHENYLAMINE; IMINE; MACROCYCLIC COMPOUND; QUINODIIMINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLIC POTENTIOMETRY; MOLECULAR INTERACTION; OXIDATION REDUCTION REACTION; SYNTHESIS;

EID: 81055144566     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo201650t     Document Type: Article

References (25)

1. Geniès, E. M.; Boyle, A.; Lapkowski, M.; Tsintavis, C. Synth. Met. 1990, 36, 139-182
2. Moon, D. K.; Osakada, K.; Maruyama, T.; Yamamoto, T. Makromol. Chem. 1992, 193, 1723-1728
3. Kang, E. T.; Neoh, K. G.; Tan, K. L. Prog. Polym. Sci. 1998, 23, 277-324
4. Hirao, T.; Higuchi, M.; Ohshiro, Y.; Ikeda, I. Chem. Lett. 1993, 1889-1890
5. Moon, D.-K.; Ezuka, M.; Maruyama, T.; Osakada, K.; Yamamoto, T. Macromolecules 1993, 26, 364-369
6. Moon, D.-K.; Ezuka, M.; Maruyama, T.; Osakada, K.; Yamamoto, T. Makromol. Chem. 1993, 194, 3149-3155
7. Higuchi, M.; Imoda, D.; Hirao, T. Macromolecules 1996, 29, 8277-8279
8. Gospodinova, N.; Terlemezyan, L. Prog. Polym. Sci. 1998, 23, 1443-1484
9. MacDiarmid, A. G. Angew. Chem., Int. Ed. 2001, 40, 2581-2590
10. Hirao, T.; Fukuhara, S.; Otomaru, Y.; Moriuchi, T. Synth. Met. 2001, 123, 373-376
11. Sadighi, J. P.; Singer, R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 4960-4976
12. Dufour, B.; Rannou, P.; Travers, J. P.; Pron, A.; Zagórska, M.; Korc, G.; Kulszewicz-Bajer, I.; Quillard, S.; Lefrant, S. Macromolecules 2002, 35, 6112-6120
13. Gao, J.; Liu, D.-G.; Sansiñena, J.-M.; Wang, H.-L. Adv. Funct. Mater. 2004, 14, 537-543
14. Sakurai, H.; Ritonga, M. T. S.; Shibatani, H.; Hirao, T. J. Org. Chem. 2005, 70, 2754-2762
15. Wang, Y.; Tran, H. D.; Liao, L.; Duan, X.; Kaner, R. B. J. Am. Chem. Soc. 2010, 132, 10365-10373
16. Wei, Z.; Faul, C. F. J. Macromol. Rapid Commun. 2008, 29, 280-292
17. Hauck, S. I.; Lakshmi, K. V.; Hartwig, J. F. Org. Lett. 1999, 1, 2057-2060
18. Fukushima, W.; Kanbara, T.; Yamamoto, T. Synlett 2005, 2931-2934
19. Kanazawa, H.; Higuchi, M.; Yamamoto, K. J. Am. Chem. Soc. 2005, 127, 16404-16405
20. Zhao, Y.; Schultz, N. E.; Truhlar, D. G. J. Chem. Theory Comput. 2006, 2, 364-382
21. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
22. Stephens, P. J.; Devlin, F. J.; Chablowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623-11627
23. Hertwig, R. H.; Koch, W. Chem. Phys. Lett. 1997, 268, 345-351
24. Gaussian 09, Revision B.01; Gaussian, Inc.: Wallingford, CT, 2010. A full reference may be found in the Supporting Information.
25. Avogadro: An Open-Source Molecular Builder and Visualization Tool; Version 1.0.3. http://avogadro.openmolecules.net/.