Preparation and characterisation of iodo-functionalised azobenzene derivatives of the type I-p-C6H4-N=N-p-C6H 4-X

Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences

Volumn 63, Issue 12, 2008, Pages 1395-1401

  Siemeling, Ulrich ^a   Bruhn, Clemens ^a   Meier, Mario ^a   Schirrmacher, Christian ^a  

^a UNIVERSITY OF KASSEL   (Germany)

Author keywords

Azo coupling; Azobenzene; Crystal structure; Ferrocene; Nitroso amine condensation

Indexed keywords

AZOBENZENE; IRON COMPOUNDS; NAPHTHALENE; ORGANOMETALLICS; PRASEODYMIUM COMPOUNDS; SINGLE CRYSTALS;

AZO COUPLING; AZOBENZENE DERIVATIVES; FERROCENE DERIVATIVE; FERROCENES; FERROCENYL; NITROSO; SINGLE CRYSTAL X-RAY STRUCTURES;

CRYSTAL STRUCTURE;

EID: 58049176422     PISSN: 09320776     EISSN: None     Source Type: Journal    
DOI: 10.1515/znb-2008-1208     Document Type: Article

References (50)

1. For recent reviews, see: a) S. Onclin, B. J. Ravoo, D. N. Reinhoudt, Angew. Chem. 2005, 117, 6438-6462;
2. Angew. Chem. Int. Ed. 2005, 44, 6282-6304;
3. b) J. C Love, L. A. Estroff, J. K. Kriebel, R. G. Nuzzo, C. M. Whitesides, Chem. Rev. 2005, 105, 1103-1170;
4. c) F. Schreiber, J. Phys.: Condens. Matter 2004, 16, R881-R900;
5. d) F. Schreiber, Prog. Surf. Sci. 2000, 65, 151-257.
6. For recent references, see: a) T. Weidner, F. Bretthauer, N. Ballav, H. Motschmann, H. Orendi, C. Bruhn, U. Siemeling, M. Zharnikov, Langmuir 2008, 24, 11691-11670;
7. b) J. M. Mativetsky, G. Pace, M. Elbing, M. A. Rampi, M. Mayor, P. Samori, J. Am. Chem. Soc. 2008, 130, 9192-9193;
8. c) X. Zhang, Y. Wen, Y Li, G. Li, S. Du, H. Guo, L. Yang, L. Jiang, H. Gao, Y. Song, J. Phys. Chem. C 2008, 112, 8288-8293;
9. d) V. Ferri, M. Elbing, G. Pace, M. D. Dickey, M. Zharnikov, P. Samori, M. Mayor, M. A. Rampi, Angew. Chem. 2008, 120, 3455-3457;
10. Angew. Chem. Int. Ed. 2008, 47, 3407-3409;
11. e) A. S. Kumar, T. Ye, T. Takami, B.-C. Yu, A. K. Flatt, J. M. Tour, P. S. Weiss, Nano Lett. 2008, 8, 1644-1648;
12. f) P. Dietrich, F. Michalik, R. Schmidt, C. Gahl, G. Mao, M. Breusing, M. B. Raschke, B. Priewisch, T. Elsässer, R. Mendelsohn, M. Weinelt, K. Rück-Braun, Appl. Phys. A 2008, 93, 285-292;
13. g) G. Pace, V. Ferri, C. Grave, M. Elbing, C. von Hänisch, M. Zharnikov, M. Mayor, M. A. Rampi, P. Samori, Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 9937-9942;
14. h) D. Pearson, A. J. Downard, A. Muscroft-Taylor, A. D. Abell, J. Am. Chem. Soc. 2007, 129, 14862-14863;
15. i) N. Delorme, J.-F. Bardeau, A. Bulou, F. Poncin-Epaillard, Langmuir 2005, 21, 12278-12282;
16. j) M. Ito, TX. Wei, P.-L. Chen, H. Akiyama, M. Matsumoto, K. Tamada, Y. Yamamoto, J. Mater. Chem. 2005, 15, 478-483;
17. k) R. Micheletto, M. Yokokawa, M. Schroeder, D. Hobara, Y. Ding, Kakiuchi, Appl. Surf Sci. 2004, 228, 265-270;
18. l) S. Sortino, S. Petralia, S. Conoci, S. Di Bella, J. Mater. Chem. 2004, 14, 811-813;
19. m) F. Hamelmann, U. Heinzmann, U. Siemeling, F. Bretthauer, J. Vor der Brüggen, Appl. Surf. Sci. 2004, 222, 1-5;
20. n) Z. Wang, M. J. Cook, A.-M. Nygård, D. A. Russell, Langmuir 2003, 19, 3779-3784;
21. o) K. Tamada, H. Akiyama, T.-X. Wei, S.-A. Kim, Langmuir 2003, 19, 2306-2312;
22. p) S. Yasuda, T. Nakamura, M. Matsumo, H. Shigekawa, J. Am. Chem. Soc 2003, 125, 16430-16434;
23. for a review of earlier work, see: q) Z. Sekkat, W. Knoll, in Photoreactive Organic Thin Films, (Eds.: Z. Sekkat, W. Knoll), Academic Press, San Diego, CA, 2002, chapter 4.
24. See, for example: a) H. Rau in Photoreactive Organic Thin Films (Eds.: Z. Sekkat, W. Knoll), Academic Press, San Diego, CA, 2002, chapter 1.
25. b) H. Rau in Photochemistry and Photophysics, Vol. 2 (Ed.: J. F. Rabek), CRC Press, Boca Raton, FL, 1990, chapter 4.
26. J. M. Buriak, Chem. Rev. 2002, 102, 1271-1308.
27. a) Y. Liu, Z.-X. Yang, Y Chen, J. Org. Chem. 2008, 73, 5298-5304;
28. b) X. Shen, H. Liu, Y Li, S. Liu, Macromolecules 2008, 41, 2421-2425;
29. c) I. Yildiz, S. Ray, T. Benelli, F. M. Raymo, J. Mater. Chem. 2008, 18, 3940-3947;
30. d) S. Zarwell, K. Rück-Braun, Tetrahedron Lett. 2008, 49, 4020-4025;
31. e) D. Takamatsu, Y Yamakoshi, K.-I. Fukui, J. Phys. Chem. B 2006, 110, 1986-1970.
32. a) M. Meier, Dissertation, Universität Kassel, 2008;
33. b) U. Siemeling, M. Meier, C. Bruhn, T. Weidner, M. Zharnikov, unpublished results.
34. In the case of X = OMe and NMe2, the compounds have been previously prepared by a different method (azo-coupling). However, essential details concerning their preparation and characterisation have been unavailable: S. Yildirir, M. Toy, Marmara Universitesi Fen Bilimleri Dergisi 1989, 213-225.
35. M. Y. Paik, S. Krishnan, F. You, X. Li, A. Hexemer, Y. Ando, S. H. Kang, D. A. Fischer, E. J. Kramer, C. K. Ober, Langmuir 2007, 23, 5110-5119.
36. Seminal paper: a) A. Baeyer, Ber. Dtsch. Chem. Ges. 1874, 7, 1638-1640;
37. detailed mechanistic studies: b) K. Ueno, S. Akiyoshi, J. Am. Chem. Soc. 1954, 76, 3670-3672;
38. c) Y. Ogata, Y. Takagi, J. Am. Chem. Soc. 1958, 80, 3591-3595.
39. D. A. Fletcher, B. G. Gowenlock, K. G. Orell, J. Chem. Soc., Perkin Trans. 1997, 2, 2201-2205.
40. rd ed., Wiley-VCH, Weinheim, 2003, chapter 7.3.
41. J. Harada, K. Ogawa, J. Am. Chem. Soc. 2004, 126, 3539-3544.
42. B. Cordero, V. Gómez, A. E. Platero-Prats, M. Revés, J. Echevarría, E. Cremades, F. Barragán, S. Alvarez, Dulton Trans. 2008, 2832-2838.
43. Seminal paper: M. G. Drew, G. R. Willey, J. Chem. Soc., Perkin Trans. 1986, 2, 215-220.
44. D. Braga, F. Grepioni, E. Tedesco, Organometallics 1998, 77, 2669-2672.
45. M. Y. Paik, S. Krishnan, F. You, X. Li, A. Hexemer, Y. Ando, S. H. Kang, D. A. Fischer, E. J. Kramer, C. K. Ober, Langmuir 2007, 23, 5110-5119.
46. J. Polin, H. Schottenberger, Org. Synth. 1996, 73, 262-269.
47. J.-F. Létard, P. Guionneau, E. Codjovi, O. Lavastre, G. Bravie, D. Chasseau, O. Kahn, J. Am. Chem. Soc. 1997, 119, 10861-10862.
48. J. J. Stapleton, T. A. Daniel, S. Uppili, O. M. Cabarcos, J. Naciri, R. Shashidhar, D. L. Aliara, Langmuir 2005, 21, 11061-11070.
49. Stoe & Cie, X-RED (version 1.06), Program for numerical absorption correction, Darmstadt (Germany) 2004.
50. G. M. Sheldrick, SHELXS-97 and SHELXL-97, Programs for crystal structure solution and refinement, University of Göttingen, Göttingen (Germany) 1997.