Near-infrared light activated azo-BF2 switches

Journal of the American Chemical Society

Volumn 136, Issue 38, 2014, Pages 13190-13193

  Yang, Yin ^a   Hughes, Russell P ^a   Aprahamian, Ivan ^a  

^a Lamont Doherty Earth Observatory   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ISOMERS;

AZO COMPOUND; BATHOCHROMIC SHIFT; CIS ISOMERS; DIMETHYLAMINES; ELECTRON-DONATING; GLUTATHIONES; NEAR INFRARED LIGHT; PARA SUBSTITUTION;

INFRARED DEVICES;

AZO COMPOUND; DIMETHYLAMINE; GLUTATHIONE; GLUTATHIONE REDUCTASE; BORON DERIVATIVE;

AQUEOUS SOLUTION; ARTICLE; CIS ISOMER; CIS TRANS ISOMERISM; ELECTRON; ELECTRON TRANSPORT; HALF LIFE TIME; HYDROLYSIS; INFRARED RADIATION; ISOMERIZATION; PHOTOACTIVATION; REDUCTION; SUBSTITUTION REACTION; CHEMICAL STRUCTURE; CHEMISTRY; HALOGENATION; ISOMERISM; OXIDATION REDUCTION REACTION;

AZO COMPOUNDS; BORON COMPOUNDS; HALOGENATION; HYDROLYSIS; INFRARED RAYS; ISOMERISM; MODELS, MOLECULAR; OXIDATION-REDUCTION;

EID: 84924678516     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja508125n     Document Type: Article

References (36)

1. Kalka, K.; Merk, H.; Mukhtar, H. J. Am. Acad. Dermatol. 2000, 42, 389-413.
2. Smith, K. C., Ed. The Science of Photobiology; Plenum Press: New York, 1977.
3. (a) Irie, M. Chem. Rev. 2000, 100, 1683-1684.
4. Durr, H.; Bouas-Laurent, H., Eds. Photochromism: Molecules and Systems; Elsevier: Amsterdam, The Netherlands, 2003.
5. Velema, W. A.; Szymanski, W.; Feringa, B. L. J. Am. Chem. Soc. 2014, 136, 2178-2191.
6. Sjulson, L.; Miesenbçck, G. Chem. Rev. 2008, 108, 1588-1602.
7. (b) Fehrentz, T.; Schönberger, M.; Trauner, D. Angew. Chem., Int. Ed. 2011, 50, 12156-12182.
8. (b) Brieke, C.; Rohrbach, F.; Gottschalk, A.; Mayer, G.; Heckel, A. Angew. Chem., Int. Ed. 2012, 51, 8446-8476.
9. Bandara, H. M. D.; Burdette, S. C. Chem. Soc. Rev. 2012, 41, 1809-1825.
10. (a) Kay, E. R.; Leigh, D. A.; Zerbetto, F. Angew. Chem., Int. Ed. 2007, 46, 72-191.
11. (b) Balzani, V.; Credi, A.; Venturi, M. Molecular Devices and Machines: Concepts and Perspectives for the Nanoworld; Wiley-VCH: Weinheim, Germany, 2008.
12. (b) Stoddart, J. F. Chem. Soc. Rev. 2009, 38, 1802-1820.
13. Feringa, B. L.; Browne, W. R., Eds. Molecular Switches; Wiley-VCH: Weinheim, Germany, 2011.
14. (a) Brash, D.; Rudolph, J.; Simon, J.; Lin, A.; Mckenna, G.; Baden, H.; Halperin, A.; Ponten, J. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 1012-10128.
15. (b) Tamai, T. K.; Vardhanabhuti, V.; Foulkes, N. S.; Whitmore, D. Curr. Biol. 2004, 14, R104-R105.
16. (c) Banerjee, G.; Gupta, N.; Kapoor, A.; Raman, G. Cancer Lett. 2005, 223, 275-284.
17. (a) Sadovski, O.; Beharry, A. A.; Zhang, F.; Woolley, G. A. Angew. Chem., Int. Ed. 2009, 48, 1484-1486.
18. (b) Wegner, H. A. Angew. Chem., Int. Ed. 2012, 51, 4787-4788.
19. (a) Beharry, A. A.; Sadovski, O.; Woolley, G. A. J. Am. Chem. Soc. 2011, 133, 19684-19687.
20. (b) Bleger, D.; Schwarz, J.; Brouwer, A.; Hecht, S. J. Am. Chem. Soc. 2012, 134, 20597-20600.
21. (c) Samanta, S.; Beharry, A. A.; Sadovski, O.; McCormick, T. M.; Babalhavaeji, A.; Tropepe, V.; Woolley, G. A. J. Am. Chem. Soc. 2013, 135, 9777-9784.
22. (d) Samanta, S.; McCormick, T. M.; Schmidt, S. K.; Seferos, D. S.; Woolley, G. A. Chem. Commun. 2013, 49, 10314-10316.
23. (a) Kurihara, M.; Hirooka, A.; Kume, S.; Sugimoto, M.; Nishihara, H. J. Am. Chem. Soc. 2002, 124, 8800-8801.
24. (b) Venkataramani, S.; Jana, U.; Dammaschk, M.; Sönnichsen, F. D.; Tuczek, F.; Herges, R. Science 2011, 331, 445-448.
25. Siewertsen, R.; Neumann, H.; Buchheim-Stehn, B.; Herges, R.; Nather, C.; Renth, F.; Temps, F. J. Am. Chem. Soc. 2009, 131, 15594-15595.
26. Wang, L.; Dong, H.; Li, Y.; Xue, C.; Sun, L.-D.; Yan, C.-H.; Li, Q. J. Am. Chem. Soc. 2014, 136, 4480-4483.
27. Sun, L.-D.; Wang, Y.-F.; Yan, C.-H. Acc. Chem. Res. 2014, 47, 1001-1009.
28. Yang, Y.; Hughes, R. P.; Aprahamian, I. J. Am. Chem. Soc. 2012, 134, 15221-15224.
29. 2-azo compound that does not switch, please see: Li, Y.; Patrick, B. O.; Dolphin, D. J. Org. Chem. 2009, 74, 5237-5243.
30. Mustroph, H. Dyes Pigm. 1991, 15, 129-137.
31. Blevins, A. A.; Blanchard, G. J. J. Phys. Chem. B 2004, 108, 4962-4968.
32. Mustroph, H. Dyes Pigm. 1991, 16, 223-230.
33. (a) Ray, D.; Foy, J. T.; Hughes, R. P.; Aprahamian, I. Nat. Chem. 2012, 4, 757-762.
34. (b) Su, X.; Voskian, S.; Hughes, R. P.; Aprahamian, I. Angew. Chem., Int. Ed. 2013, 52, 10734-10739.
35. (c) Tatum, L.; Su, X.; Aprahamian, I. Acc. Chem. Res. 2014, 47, 2141-2149.
36. (d) Su, X.; Aprahamian, I. Chem. Soc. Rev. 2014, 43, 1963-1981.