Synthesis and property studies of cyclotrisazobenzenes

European Journal of Organic Chemistry

Volumn , Issue 32, 2009, Pages 5647-5652

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

^a UNIVERSITY OF BASEL   (Switzerland)

Author keywords

Azo compounds; Macrocycles; Mills reaction; Photochemistry

Indexed keywords

EID: 70549106878     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200900861     Document Type: Article

References (71)

1. a) J. Griffith, Chem. Soc. Rev. 1972, 1, 481;
2. b) H. Rau, Photochromism: Molecules and Systems (Eds.: H. Dürr, H. BouasLaurent), Elsevier, Amsterdam, 2003.
3. For recent theoretical studies on the thermal and photochemical isomerization mechanism of azobenzene, see: a) I. Conti, M. Garavelli, G. Orlandi, J. Am. Chem. Soc. 2008, 130, 5216;
4. b) C. Ciminelli, G. Granucci, M. Persico, Chem. Eur. J. 2004, 10, 2327;
5. c) E. W.-G Diau, J. Phys. Chem. A 2004, 108, 950;
6. d) A. Cembran, F. Bernardi, M. Garavelli, L. Gagliardi, G. Orlandi, J. Am. Chem. Soc. 2004, 126, 3234;
7. e) T. Ikegami, N. Kurita, H. Sekino, Y. Ishikawa, J. Phys. Chem. A 2003, 107, 4555;
8. f) T. Ishikawa, T. Noro, T. Shoda, J. Chem. Phys. 2001, 115, 7503;
9. g) W. Sokalski, A. R. W. Góra, W. Bartkowiak, P. Kobylinski, J. Sworakowski, A. Chyla, J. Leszczynski, J. Chem. Phys. 2001, 114, 5504;
10. h) P. Cattaneo, M. Persico, Phys. Chem. Chem. Phys. 1999, 1, 4739. For recent experimental studies on the photochemical isomerization mechanism of azobenzene, see:
11. i) Y.-C. Lu, E. W.-G. Diau, H. Rau, J. Phys. Chem. A 2005, 109, 2090;
12. j) C.-W. Chang, Y.-C. Lu, T.-T. Wang, E. W.-G. Diau, J. Am. Chem. Soc. 2004, 126, 10109;
13. k) H. Satzger, C. Root, M. Braun, J. Phys. Chem. A 2004, 108, 6265;
14. l) H. Satzger, S. Spörlein, C. Root, J Wachtveitl, W. Zinth, P. Gilch, Chem. Phys. Lett. 2003, 372, 216;
15. m) T. Schultz, J. Quenneville, B. Levine, A. Toniolo, T. J. Martinez, S. Lochbrunner, M. Schmitt, J. R Shaffer, M. Z. Zgierski, A. Stolow, J. Am. Chem. Soc. 2003, 125, 8098;
16. n) T. Fujino, S. Y. Arzhantsev, T. Tahara, Bull. Chem. Soc. Jpn. 2002, 75, 1031;
17. o) T. Fujino, S. Y. Arzhantsev, T Tahara, J. Phys. Chem. A 2001, 105, 8123;
18. p) T. Fujino, T. Tahara, J. Phys. Chem. A 2000, 104, 4203.
19. a) K. G. Yager, C. J. Barrett, J. Photoch. Photobiol. A 2006, 182, 250;
20. b) C. Dugave, L. Demange, Chem. Rev. 2003, 103, 2475;
21. c) A. Natansohn, R. Rochon, Chem. Rev. 2002, 102, 4139;
22. d) I. Willner, B. Willner, in Bioorganic Photochemistry: Biological Applications of Photochemical Switches (Eds.: H. Morrison), Wiley, New York, 1993, vol.2, pp. 1110;
23. e) K. Ichimura, Photochromism: Molecules and Systems (Eds.: H. Dürr, H. Bouas-Laurent), Elsevier, Amsterdam, 1990, p. 903;
24. f) G. S. Kumar, D. C. Neckers, Chem. Rev. 1989, 89, 1915.
25. For recent examples, see: a) H.-M. Kang, H.-Y. Kim, J.-W. Jung, C.-G. Cho, J. Org. Chem. 2007, 72, 679;
26. b) P. Rajakumar, B. Senthilkumar, K. Srinivasan, Aust. J. Chem. 2006, 59, 75;
27. c) N. Tamaoki, J. Synth. Org. Chem. Jpn. 2005, 63, 370;
28. d) C. Ciminelli, G. Granucci, M. Persico, J. Chem. Phys. 2005, 123, 174317.
29. Y. Norikane, R. Katoh, N. Tamaoki, Chem. Commun. 2008, 1898.
30. Y. Norikane, K. Kitamoto, N. Tamaoki, J. Org. Chem. 2003, 68, 8291.
31. a) J. S. Ritch, T. Chivers, Angew. Chem. Int. Ed. 2007, 46, 4610;
32. b) S. Jarosz, A. Listkowski, Curr. Org. Chem. 2006, 10, 643;
33. c) G. Gokel, W. M. Leevy, M. E. Weber, Chem. Rev. 2004, 104, 2723;
34. d) J. W. Steed, Coord Chem. Rev. 2001, 215, 171;
35. e) J. S. Bradshaw, R. M. Izatt, Acc. Chem. Res. 1997, 30, 338.
36. C. D. Gutsche, Calixarenes, Royal Society of Chemistry, Cambridge, UK, 1989.
37. H. Hilpert, L. Hoesch, A. S. Dreiding, Helv. Chim. Acta 1985, 68, 325.
38. P. Skrabal, M. Hohl-Blumer, Helv. Chim. Acta 1976, 59, 2906.
39. 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. Lili, F. Marotti, A. Schlegel, R. R. Schüttler, P. J Skinner, P. Seiler, Y. Yamakoshi, Adv. Fund. Mater. 2006, 16, 147.
40. a) N. A. Noureldin, J. W. Bellegarde, Synthesis 1999, 939;
41. b) M. Hedayatullah, J. P. Dechatre, L. Dénivelle, Tetrahedron Lett. 1975, 16, 2039;
42. c) B. Ortiz, P. Villanueva, F. Walls, J. Org. Chem. 1972, 37, 2748;
43. d) E. Haselbach, Helv. Chim. Acta 1970, 53, 1526;
44. e) O. H. Wheeler, D. Gonzalez, Tetrahedron 1964, 20, 189.
45. a) S. Wang, X. Wang, L. Li, R. C. Advincula, J Org. Chem. 2004, 69, 9073;
46. b) S. Wada, M. Urano, H. Suzuki, J. Org. Chem. 2002, 67, 8254;
47. c) E. Tauer, R. Machinek, Liebigs Ann. 1996, 1213;
48. d) R. F. Nystrom, W. G. Brown, J. Am. Chem. Soc. 1948, 70, 3738.
49. For diazo couplings, see: a) M. J. Jones, Organic Chemistry, 2nd ed., W. W. Norton & Company, New York, 2000;
50. b) A. F. Hegarty, The Chemistry of Diazonium and Diazo Groups, Wiley, New York, 1978;
51. c) P. Ruggli, E. Iselin, Helv. Chim. Acta 1947, 30, 739;
52. d) P. Ruggli, W. Wüst, Helv. Chim. Acta 1945, 28, 781;
53. e) P. Ruggli, L. Rohner, Helv. Chim. Acta 1942, 25, 1533. For a Pd-catalyzed two-step procedure, see:
54. [4a]; g) Y.-K. Lim, K.-S. Lee, C.-G. Cho, Org. Lett. 2003, 5, 979.
55. a) G. Pace, V. Ferri, C. Grave, M. Elbing, C. von Haenisch, M. Zharnikov, M. Mayor, M. A. Rampi, P. Samori, Proc Natl. Acad. Sci. USA 2007, 104, 9937;
56. b) M. H. Davey, V. Y. Lee, R. D. Miller, T. J. Marks, J. Org. Chem. 1999, 64, 4976;
57. c) I. Szele, H. Zollinger, Top. Curr. Chem. 1983, 112, 1;
58. d) H. Feuer, The Chemistry of the Nitro and Nitroso Groups, Interscience, New York, 1969, vol.1;
59. e) C. Mills, J. Chem. Soc. 1895, 67, 925; see also Ref. 14c-e.
60. G. Crank, M. I. H. Makin, Tetrahedron Lett. 1979, 23, 2169.
61. L. K. Dyall, Aust. J. Chem. 1979, 32, 643.
62. B. Priewisch, K. Rück-Braun, J. Org. Chem. 2005, 70, 2350.
63. a) J. Rosevear, J. F. K. Wilshire, Aust. J. Chem. 1986, 38, 732;
64. b) S.-L. Dong, M. Löweneck, T. E. Schrader, J. Schreier, W. Zinth, L. Moroder, C. Renner, Chem. Eur.. J 2006, 12, 1114.
65. H. Rau, J. Rebek (Eds.) in Photochemistry and Photophysics, CRC Press, Boca Raton, FL, 1990, vol.2, p. 119.
66. A. S. Dreiding, J. H. Bieri, R. Prewo, A. Linden, H. Hilpert, L. Hoesch, private communication to the CCDC, 1993, refcode HACKEB.
67. -1. The APEX software package (Apex2, Version 2, User Manual, M86-E01078, Bruker Analytical X-ray Systems, Inc., Madison, WI, 2006) was used for data collection and integration. From a total of 28498 reflections, 5100 were independent (merging r = 0.038). From these, 4575 were considered as observed [I> 2.0σ(I)] and were used to refine 579 parameters. The structure was solved by direct methods using the program SIR92 (A. Altomare, G. Cascarano, G Giacovazzo, A. Guagliardi, M. C Burla, G Polidori, M. Camalli, J Appl. Crystallogr. 1994, 27, 435).
68. Leastsquares refinement against F was carried out on all non-hydrogen atoms by using the program CRYSTALS (R W Betteridge, J R. Carruthers, R. I. Cooper, K. Prout, D. J. Watkin, J Appl. Crystallogr. 2003, 36, 1487).
69. -3. Chebychev polynomial weights (D. J. Watkin, Acta Crystallogr., Sect. A 1994, 50, 411;
70. E. Prince, Mathematical Techniques in Crystallography and Materials Science, Springer-Verlag, New York, 1982)
71. were used to complete the refinement. One of the molecules shows disorder, which was modeled by using appropriate restraints. Plots were produced by using ORTEP3 for Windows (L. J. Farrugia, J Appl. Crystallogr. 1997, 30, 565). CCDC-730161 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.