Synthesis, properties, and redox behavior of tetracyanobutadiene and dicyanoquinodimethane chromophores bearing two azulenyl substituents

Journal of Organic Chemistry

Volumn 78, Issue 24, 2013, Pages 12513-12524

  Shoji, Taku ^a   Maruyama, Mitsuhisa ^a   Shimomura, Erika ^a   Maruyama, Akifumi ^a   Ito, Shunji ^b   Okujima, Tetsuo ^c   Toyota, Kozo ^d   Morita, Noboru ^d  

^a SHINSHU UNIVERSITY   (Japan)

^b HIROSAKI UNIVERSITY   (Japan)

^c EHIME UNIVERSITY   (Japan)

^d TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

[2 + 2] CYCLOADDITION; CT ABSORPTION BAND; ELECTROCHEMICAL REDUCTIONS; PALLADIUM-CATALYZED; REDOX BEHAVIOR; REDUCTION WAVE; TETRACYANOETHYLENE; UV-VIS SPECTRA;

ELECTROLYTIC REDUCTION; SYNTHESIS (CHEMICAL);

CHROMOPHORES;

1,3 BUTADIENE DERIVATIVE; ACETYLENE DERIVATIVE; ALKYNE DERIVATIVE; AZULENE DERIVATIVE; DICYANOQUINODIMETHANE; METHANE; PALLADIUM; TETRACYANOBUTADIENE; TETRACYANOETHYLENE; UNCLASSIFIED DRUG;

ABSORPTION; ALKYNYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHROMATOPHORE; COLOR; CYCLIC POTENTIOMETRY; CYCLIZATION; CYCLOADDITION; DIFFERENTIAL PULSE VOLTAMMETRY; ELECTROCHEMICAL ANALYSIS; OXIDATION REDUCTION POTENTIAL; PROTON NUCLEAR MAGNETIC RESONANCE; SONOGASHIRA REACTION; SYNTHESIS; ULTRAVIOLET RADIATION;

EID: 84890901351     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo402104n     Document Type: Article

References (55)

1. Brédas, J. L.; Adant, C.; Tackx, P.; Persoons, A.; Pierce, B. M. Chem. Rev. 1994, 94, 243-278
2. Bendikov, M.; Wudl, F.; Perepichka, D. F. Chem. Rev. 2004, 104, 4891-4945
3. Hünig, S.; Herberth, E. Chem. Rev. 2004, 104, 5535-5564
4. Baumgartner, T.; Réau, R. Chem. Rev. 2006, 106, 4681-4727
5. Clavier, G.; Audebert, P. Chem. Rev. 2010, 110, 3299-3314
6. Kivala, M.; Stanoeva, T.; Michinobu, T.; Frank, B.; Gescheidt, G.; Diederich, F. Chem.-Eur. J. 2008, 14, 7638-7647
7. Esembeson, B.; Scimeca, M. L.; Michinobu, T.; Diederich, F.; Biaggio, I. Adv. Mater. 2008, 20, 4584-4587
8. Frank, B. B.; Blanco, B. C.; Jakob, S.; Ferroni, F.; Pieraccini, S.; Ferrarini, A.; Boudon, C.; Gisselbrecht, J.-P.; Seiler, P.; Spada, G. P.; Diederich, F. Chem.-Eur. J. 2009, 15, 9005-9016
9. Koos, C.; Vorreau, P.; Vallaitis, T.; Dumon, P.; Bogaerts, W.; Baets, R.; Esembeson, B.; Biaggio, I.; Michinobu, T.; Diederich, F.; Freude, W.; Leuthold, J. Nat. Photonics 2009, 3, 216-219
10. Frank, B. B.; Kivala, M.; Blanco, B. C.; Breiten, B.; Schweizer, W. B.; Laporta, P. R.; Biaggio, I.; Jahnke, E.; Tykwinski, R. R.; Boudon, C.; Gisselbrecht, J.-P.; Diederich, F. Eur. J. Org. Chem. 2010, 2487-2503
11. Breiten, B.; Wu, Y.-L.; Jarowski, P. D.; Gisselbrecht, J.-P.; Boudon, C.; Griesser, M.; Onitsch, C.; Gescheidt, G.; Schweizer, W. B.; Langer, N.; Lennartz, C.; Diederich, F. Chem. Sci. 2011, 2, 88-93
12. Lacy, A. R.; Vogt, A.; Boudon, C.; Gisselbrecht, J.-P.; Schweizer, W. B.; Diederich, F. Eur. J. Org. Chem. 2013, 869-879
13. Tchitchanov, B. H.; Chiu, M.; Jordan, M.; Kivala, M.; Schweizer, W. B.; Diederich, F. Eur. J. Org. Chem. 2013, 3729-3740
14. Fujita, H.; Tsuboi, K.; Michinobu, T. Macromol. Chem. Phys. 2011, 212, 1758-1766
15. Li, Y.; Ashizawa, M.; Uchida, S.; Michinobu, T. Macromol. Rapid Commun. 2011, 32, 1804-1808
16. Michinobu, T.; Seo, C.; Noguchi, K.; Mori, T. Polym. Chem. 2012, 3, 1427-1435
17. Li, Y.; Ashizawa, M.; Uchida, S.; Michinobu, T. Polym. Chem. 2012, 3, 1996-2005
18. Kivala, M.; Boudon, C.; Gisselbrecht, J.-P.; Seiler, P.; Gross, M.; Diederich, F. Chem. Commun. 2007, 4731-4733
19. Kivala, M.; Boudon, C.; Gisselbrecht, J.-P.; Enko, B.; Seiler, P.; Müller, I. B.; Langer, N.; Jarowski, P. D.; Gescheidt, G.; Diederich, F. Chem.-Eur. J. 2009, 15, 4111-4123
20. Kato, S.; Kivala, M.; Schweizer, W. B.; Boudon, C.; Gisselbrecht, J.-P.; Diederich, F. Chem.-Eur. J. 2009, 15, 8687-8691
21. Fesser, P.; Iacovita, C.; Wäckerlin, C.; Vijayaraghavan, S.; Ballav, N.; Howes, K.; Gisselbrecht, J.-P.; Crobu, M.; Boudon, C.; Stohr, M.; Jung, T. A.; Diederich, F. Chem.-Eur. J. 2011, 17, 5246-5250
22. Yuan, Y.; Michinobu, T. J. Polym. Sci., Part A: Polym. Chem. 2011, 49, 225-233
23. Washino, Y.; Michinobu, T. Macromol. Rapid Commun. 2011, 32, 644-648
24. Jarowski, P. D.; Wu, Y.-L.; Boudon, C.; Gisselbrecht, J.-P.; Gross, M.; Schweizer, W. B.; Diederich, F. Org. Biomol. Chem. 2009, 7, 1312-1322
25. Silvestri, F.; Jordan, M.; Howes, K.; Kivala, M.; Rivera-Fuentes, P.; Boudon, C.; Gisselbrecht, J.-P.; Schweizer, W. B.; Seiler, P.; Chiu, M.; Diederich, F. Chem.-Eur. J. 2011, 17, 6088-6097
26. Tancini, F.; Wu, Y.-L.; Schweizer, W. B.; Gisselbrecht, J.-P.; Boudon, C.; Jarowski, P. D.; Beels, M. T.; Biaggio, I.; Diederich, F. Eur. J. Org. Chem. 2012, 2756-2765
27. Zeller, K.-P. Azulene. In Methoden der Organischen Chemie (Houben-Weyl), 4 th ed.; Kropf, H., Ed.; Thieme: Stuttgart, 1985; Vol. V, Part 2c, pp 127-418.
28. Ito, S.; Inabe, H.; Okujima, T.; Morita, N.; Watanabe, M.; Harada, N.; Imafuku, K. J. Org. Chem. 2001, 66, 7090-7101
29. Ito, S.; Okujima, T.; Morita, N. J. Chem. Soc. Perkin Trans. 1 2002, 1896-1905
30. Ito, S.; Inabe, H.; Morita, N.; Ohta, K.; Kitamura, T.; Imafuku, K. J. Am. Chem. Soc. 2003, 125, 1669-1680
31. Ito, S.; Kubo, T.; Morita, N.; Ikoma, T.; Tero-Kubota, S.; Tajiri, A. J. Org. Chem. 2003, 68, 9753-9762
32. Ito, S.; Inabe, H.; Morita, N.; Tajiri, A. Eur. J. Org. Chem. 2004, 1774-1780
33. Ito, S.; Kubo, T.; Morita, N.; Ikoma, T.; Tero-Kubota, S.; Kawakami, J.; Tajiri, A. J. Org. Chem. 2005, 70, 2285-2293
34. Ito, S.; Iida, T.; Kawakami, J.; Okujima, T.; Morita, N. Eur. J. Org. Chem. 2009, 5355-5364
35. Shoji, T.; Shimomura, E.; Maruyama, M.; Ito, S.; Okujima, T.; Morita, N. Eur. J. Org. Chem. 2013, 957-964
36. Shoji, T.; Ito, S.; Toyota, K.; Yasunami, M.; Morita, N. Chem.-Eur. J. 2008, 14, 8398-8408
37. Shoji, T.; Ito, S.; Toyota, K.; Iwamoto, T.; Yasunami, M.; Morita, N. Eur. J. Org. Chem. 2009, 4316-4324
38. Shoji, T.; Maruyama, M.; Ito, S.; Morita, N. Bull. Chem. Soc. Jpn. 2012, 85, 761-773
39. Shoji, T.; Ito, S.; Okujima, T.; Morita, N. Org. Biomol. Chem. 2012, 10, 8308-8313
40. Shoji, T.; Ito, S.; Okujima, T.; Morita, N. Chem.-Eur. J. 2013, 19, 5721-5730
41. Ito, S.; Nomura, A.; Morita, N.; Kabuto, C.; Kobayashi, H.; Maejima, S.; Fujimori, K.; Yasunami, M. J. Org. Chem. 2002, 67, 7295-7302
42. Nozoe, T.; Seto, S.; Matsumura, S. Bull. Chem. Soc. Jpn. 1962, 35, 1990-1998
43. Corbet, J.-P.; Mignani, G. Chem. Rev. 2006, 106, 2651-2710
44. McDonald, R. N.; Richmond, J. M.; Curtis, J. R.; Petty, H. E.; Hoskins, T. L. J. Org. Chem. 1976, 41, 1811-1821
45. Nozoe, T.; Seto, S.; Matsumura, S.; Murase, Y. Bull. Chem. Soc. Jpn. 1962, 35, 1179-1188
46. Elwahy, A. H. M.; Hafner, K. Tetrahedron Lett. 2000, 41, 2859-2862
47. Ito, S.; Inabe, H.; Okujima, T.; Morita, N.; Watanabe, M.; Imafuku, K. Tetrahedron Lett. 2000, 41, 8343-8347
48. Reutenauer, P.; Kivala, M.; Jarowski, P. D.; Boudon, C.; Gisselbrecht, J.; Gross, M.; Diederich, F. Chem. Commun. 2007, 4898-4900
49. Silverstein, R. M.; Webster, F. X.; Kiemle, D. Spectrometric Identification of Organic Compounds, 7 th ed.; John Wiley and Sons: Weinheim, Germany, 2005.
50. Suppan, P.; Ghoneim, N. Solvatochromism; The Royal Society of Chemistry: Cambridge, 1997.
51. Christian, R. Solvent and Solvent Effects in Organic Chemistry; Wiley-VCH: Weinheim, Germany, 2004.
52. Ito, S.; Morita, N. Eur. J. Org. Chem. 2009, 4567-4579
53. Ito, S.; Shoji, T.; Morita, N. Synlett 2011, 2279-2298
54. Shoji, T.; Higashi, J.; Ito, S.; Okujima, T.; Yasunami, M.; Morita, N. Chem.-Eur. J. 2011, 17, 5116-5129
55. Shoji, T.; Higashi, J.; Ito, S.; Okujima, T.; Yasunami, M.; Morita, N. Org. Biomol. Chem. 2012, 10, 2431-2438