Oligoazobenzenes - Switching in a new dimension

Chimia

Volumn 64, Issue 3, 2010, Pages 180-183

  Reuter, Raphael ^a   Hostettler, Nik ^a   Neuburger, Markus ^a   Wegner, Hermann A ^a  

^a UNIVERSITY OF BASEL   (Switzerland)

Author keywords

Azobenzenes; Macrocycles; Mills reaction; Molecular switches; Photochromic compounds

Indexed keywords

EID: 77951570692     PISSN: 00094293     EISSN: None     Source Type: Journal    
DOI: 10.2533/chimia.2010.180     Document Type: Article

References (36)

1. (a) J. Griffith, Chem. Soc. Rev. 1972, 1, 481;
2. (b) H. Rau, 'Photochromism: Molecules and Systems', Eds. H. Dürr, H. Bouas-Laurent, Elsevier, Amsterdam, 2003.
3. (a) K. G. Yager, C. J. Barrett, J. Photoch. Photobio. A 2006, 182, 250;
4. (b) C. Dugave, L. Demange, Chem. Rev. 2003, 103, 2475;
5. (c) A. Natansohn, P. Rochon, Chem. Rev. 2002, 102, 4139;
6. (d) I. Willner, B. Willner, 'Bioorganic Photochemistry: Biological Applications of Photochemical Switches', Ed. H. Morrison, Wiley, New York, 1993, Vol.2, pp 1-110;
7. (e) K. Ichimura, 'Photochromism: Molecules and Systems', Eds. H. Dürr, H. Bouas-Laurent, Elsevier, Amsterdam, 1990, 903;
8. (f) G. S. Kumar, D. C. Neckers, Chem. Rev. 1989, 89, 1915.
9. (a) For recent examples see a)H.-M. Kang, H.-Y. Kim, J.-W. Jung, C.-G. Cho, J. Org. Chem. 2007,72, 679;
10. (b) P. Rajakumar, B. Senthilkumar, K. Srinivasan, Aust. J. Chem. 2006, 59, 75;
11. (c) N. Tamaoki, J. Syn. Org. Chem. Jpn. 2005, 63, 370;
12. (d) C. Ciminelli, G. Granucci, M. Persico, J. Chem. Phys. 2005, 123, 174317;
13. (e) Y. Norikane, K. Kitamoto, N. Tamaoki, Org. Lett. 2002, 4, 3907.
14. Y. Norikane, R. Katoh, N. Tamaoki, Chem. Comm. 2008, 16, 1898.
15. Y. Norikane, K. Kitamoto, N. Tamaoki, J. Org. Chem. 2003, 68, 8291.
16. (a) J. S. Ritch, T. Chivers, Angew. Chem., Int. Ed. 2007, 46, 4610;
17. (b) S. Jarosz, A. Listkowski, Curr. Org. Chem. 2006, 10, 643;
18. (c) G. W. Gokel, W. M. Leevy, M. E. Weber, Chem. Rev. 2004, 104, 2723;
19. (d) J. W. Steed, Coord. Chem. Rev. 2001, 215, 171;
20. (e) J. S. Bradshaw, R. M. Izatt, Acc. Chem. Res. 1997, 30, 338.
21. C. D. Gutsche, 'Calixarenes', Cambridge, Royal Society of Chemistry, UK, 1989.
22. H. Hilpert, L. Hoesch, A. S. Dreiding, Helv. Chim. Acta 1985, 2, 325.
23. P. Skrabal, M. Hohl-Blumer, Helv. Chim. Acta 1976, 8, 2906.
24. V. A. Azov, A. Beeby, M. Cacciarini, A. G. Cheetham, F. Diederich, M. Frei, J. K. Gimzewski, V. Gramlich, B. Hecht, B. Jaun, T. Latychevskaia, A. Lieb, Y. Lill, F. Marotti, A. Schlegel, R. R. Schlittler, P. J. Skinner, P. Seiler,Y. Yamakoshi, Adv. Funct. Mater. 2006, 16, 147.
25. R. Reuter, N. Hostettler, M. Neuburger, H. A. Wegner, Eur. J. Org. Chem. 2009, 32, 5647.
26. (a) C. J. Mills, Chem. Soc. 1895, 67, 925.
27. For exemplary applications of the Mills reaction see b) P. Ruggli, W. Wüst, Helv. Chim. Acta 1945, 28, 781;
28. (c) P. Ruggli, L. Rohner, Helv. Chim. Acta 1942, 25, 1533.
29. For a Pd-catalyzed two-step procedure see a) Ref. [3a];
30. (b) Y.-K. Lim, K.-S. Lee, C.-G. Cho, Org. Lett. 2003, 5, 979.
31. For diazocouplings see a) M. J. Jones, 'Organic Chemistry', 2nd ed., W. W. Norton & Company, New York, 2000;
32. (b) A. F. Hegarty, 'The Chemistry of Diazonium and Diazo Groups', Wiley, New York, 1978.
33. G. Crank, M. I. H. Makin, Tetrahedron Lett. 1979, 23, 2169.
34. A. S. Dreiding, J. H. Bieri, R. Prewo, A. Linden, H. Hilpert, L. Hoesch, Private Communication to the CCDC 1993, Refcode: HACKEB.
35. G. A. Melson, D. A. Busch, J. Am. Chem. Soc. 1965, 87, 1706.
36. E. C. Kempen, J. S. Brodbelt, Anal. Chem. 2000, 72, 5411.