Synthesis and study of redox-active acyclic triazenes: Toward electrochromic applications

Journal of Organic Chemistry

Volumn 76, Issue 9, 2011, Pages 3239-3245

  Ono, Robert J ^a   Suzuki, Yasuo ^b   Khramov, Dimitri M ^a   Ueda, Mitsuru ^b   Sessler, Jonathan L ^a,c   Bielawski, Christopher W ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

^b TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^c Yonsei University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

BULK ELECTROLYSIS; ELECTRO-CHROMIC APPLICATIONS; N-HETEROCYCLIC CARBENES; PHENYL AZIDE; REDOX PROCESS; REDOX-ACTIVE; SPECTROELECTROCHEMICAL; TRIAZENES; VISIBLE SPECTRA;

ABSORPTION SPECTROSCOPY; CARBON INORGANIC COMPOUNDS; NITROGEN COMPOUNDS; ORGANIC COMPOUNDS; SPECTROELECTROCHEMISTRY;

CYCLIC VOLTAMMETRY;

ACYCLIC TRIAZENE; AZIDE; BENZENE DERIVATIVE; CARBENE; HETEROCYCLIC COMPOUND; QUINONE DERIVATIVE; TRIAZENE DERIVATIVE; UNCLASSIFIED DRUG;

ABSORPTION; ARTICLE; CHROMATOGRAPHY; CYCLIC POTENTIOMETRY; ELECTROCHEMICAL ANALYSIS; ELECTROLYSIS; OXIDATION REDUCTION REACTION; ULTRAVIOLET SPECTROSCOPY;

EID: 79955556127     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo200139f     Document Type: Article

References (52)

1. Mortimer, R. J. Electrochim. Acta 1999, 44, 2971-2981
2. Argun, A. A.; Aubert, P. H.; Thompson, B. C.; Schwendeman, I.; Gaupp, C. L.; Hwang, J.; Pinto, N. J.; Tanner, D. B.; MacDiarmid, A. G.; Reynolds, J. R. Chem. Mater. 2004, 16, 4401-4412
3. Mortimer, R. J. Chem. Soc. Rev. 1997, 26, 147-156
4. Lampert, C. M. Sol. Energ. Mat. 1984, 11, 1-27
5. Granqvist, C. G. Sol. Energ. Mat. Sol. C 2000, 60, 201-262
6. Niklasson, G. A.; Granqvist, C. G. J. Mater. Chem. 2007, 17, 127-156
7. Monk, P.; Mortimer, R.; Rosseinsky, D. Electrochromism and Electrochromic Devices; Cambridge University Press: Cambridge, U.K., 2007.
8. Bird, C. L.; Kuhn, A. T. Chem. Soc. Rev. 1981, 10, 49-82
9. Diaz, A. F.; Logan, J. A. J. Electroanal. Chem. Interfacial Electrochem. 1980, 111, 111-114
10. Kobayashi, T.; Yoneyama, H.; Tamura, H. J. Electroanal. Chem. Interfacial Electrochem. 1984, 161, 419-423
11. Reynolds, J. R.; Kumar, A.; Reddinger, J. L.; Sankaran, B.; Sapp, S. A.; Sotzing, G. A. Synth. Met. 1997, 85, 1295-1298
12. Amb, C. M.; Dyer, A. L.; Reynolds, J. R. Chem. Mater. 2011, 23, 397-415
13. Heuer, H. W.; Wehrmann, R.; Kirchmeyer, S. Adv. Funct. Mater. 2002, 12, 89-94
14. Roznyatovskiy, V. V.; Roznyatovskaya, N. V.; Weyrauch, H.; Pinkwart, K.; Tübke, J.; Sessler, J. L. J. Org. Chem. 2010, 75, 8355-8362
15. Nadeau, J. M.; Swager, T. M. Tetrahedron 2004, 60, 7141-7146
16. Powell, A. B.; Bielawski, C. W.; Cowley, A. H. J. Am. Chem. Soc. 2009, 131, 18232-18233
17. Powell, A. B.; Bielawski, C. W.; Cowley, A. H. J. Am. Chem. Soc. 2010, 132, 10184-10194
18. Boydston, A. J.; Bielawski, C. W. Dalton Trans. 2006, 4073-4077
19. Boydston, A. J.; Rice, J. D.; Sanderson, M. D.; Dykhno, O. L.; Bielawski, C. W. Organometallics 2006, 25, 6087-6098
20. Boydston, A. J.; Williams, K. A.; Bielawski, C. W. J. Am. Chem. Soc. 2005, 127, 12496-12497
21. Coady, D. J.; Bielawski, C. W. Macromolecules 2006, 39, 8895-8897
22. Coady, D. J.; Norris, B. C.; Lynch, V. M.; Bielawski, C. W. Macromolecules 2008, 41, 3775-3778
23. Kamplain, J. W.; Bielawski, C. W. Chem. Commun. 2006, 1727-1729
24. Norris, B. C.; Bielawski, C. W. Macromolecules 2010, 43, 3591-3593
25. Norris, B. C.; Sheppard, D. G.; Henkelman, G.; Bielawski, C. W. J. Org. Chem. 2011, 76, 301-304
26. Powell, A. B.; Bielawski, C. W.; Cowley, A. H. Comments Inorg. Chem. 2010, 31, 75-82
27. Tennyson, A. G.; Kamplain, J. W.; Bielawski, C. W. Chem. Commun. 2009, 2124-2126
28. Tennyson, A. G.; Norris, B.; Bielawski, C. W. Macromolecules 2010, 43, 6923-6935
29. Williams, K. A.; Bielawski, C. W. Chem. Commun. 2010, 46, 5166-5168
30. Williams, K. A.; Boydston, A. J.; Bielawski, C. W. Chem. Soc. Rev. 2007, 36, 729-744
31. Catalano, V. J.; Etogo, A. O. Inorg. Chem. 2007, 46, 5608-5615
32. Chiu, P. L.; Chen, C. Y.; Zeng, J. Y.; Lu, C. Y.; Lee, H. M. J. Organomet. Chem. 2005, 690, 1682-1687
33. Guerret, O.; Sole, S.; Gornitzka, H.; Teichert, M.; Trinquier, G.; Bertrand, G. J. Am. Chem. Soc. 1997, 119, 6668-6669
34. Karimi, B.; Akhavan, P. F. Chem. Commun. 2009, 3750-3752
35. Mercs, L.; Neels, A.; Stoeckli-Evans, H.; Albrecht, M. Dalton Trans. 2009, 7168-7178
36. Coady, D. J.; Khramov, D. M.; Norris, B. C.; Tennyson, A. G.; Bielawski, C. W. Angew. Chem., Int. Ed. 2009, 48, 5187-5190
37. Khramov, D. M.; Bielawski, C. W. Chem. Commun. 2005, 4958-4960
38. Khramov, D. M.; Bielawski, C. W. J. Org. Chem. 2007, 72, 9407-9417
39. Andreu, R.; de Lucas, A. I.; Garín, J.; Martín, N.; Orduna, J.; Sánchez, L.; Seoane, C. Synth. Met. 1997, 86, 1817-1818
40. Choytun, D. D.; Langlois, L. D.; Johansson, T. P.; Macdonald, C. L. B.; Leach, G. W.; Weinberg, N.; Clyburne, J. A. C. Chem. Commun. 2004, 1842-1843
41. Tennyson, A. G.; Khramov, D. M.; Varnado, C. D.; Creswell, P. T.; Kamplain, J. W.; Lynch, V. M.; Bielawski, C. W. Organometallics 2009, 28, 5142-5147
42. Tennyson, A. G.; Moorhead, E. J.; Madison, B. L.; Er, J. A. V.; Lynch, V. M.; Bielawski, C. W. Eur. J. Org. Chem. 2010, 32, 6277-6282
43. Sanderson, M. D.; Kamplain, J. W.; Bielawski, C. W. J. Am. Chem. Soc. 2006, 128, 16514-16515
44. Tennyson, A. G.; Ono, R. J.; Hudnall, T. W.; Khramov, D. M.; Er, J. A. V.; Kamplain, J. W.; Lynch, V. M.; Sessler, J. L.; Bielawski, C. W. Chem. Eur. J. 2010, 16, 304-315
45. For other examples of redox-active NHCs, see: Khramov, D. M.; Rosen, E. L.; Lynch, V. M.; Bielawski, C. W. Angew. Chem., Int. Ed. 2008, 47, 2267-2270
46. Varnado, C. D., Jr; Lynch, V. M.; Bielawski, C. W. Dalton Trans. 2009, 7253-7261
47. Rosen, E. L.; Varnado, C. D.; Tennyson, A. G.; Khramov, D. M.; Kamplain, J. W.; Sung, D. H.; Cresswell, P. T.; Lynch, V. M.; Bielawski, C. W. Organometallics 2009, 28, 6695-6706
48. Tennyson, A. G.; Lynch, V. M.; Bielawski, C. W. J. Am. Chem. Soc. 2010, 132, 9420-9429
49. Park, J. S.; Karnas, E.; Ohkubo, K.; Chen, P.; Kadish, K. M.; Fukuzumi, S.; Bielawski, C. W.; Hudnall, T. W.; Lynch, V. M.; Sessler, J. L. Science 2010, 329, 1324-1327
50. Smith, P. A. S.; Boyer, J. H. J. Am. Chem. Soc. 1951, 73, 2626-2629
51. Mallory, F. B.; Smith, P. A. S.; Boyer, J. H. Org. Synth. 1957, 37, 1-3
52. Noviandri, I.; Brown, K. N.; Fleming, D. S.; Gulyas, P. T.; Lay, P. A.; Masters, A. F.; Phillips, L. J. Phys. Chem. B 1999, 103, 6713-6722