Electrolysis of tetrakis(4-N,N-dimethylaminophenyl)methane - Fragmentation of a tetraarylmethane under oxidative conditions

Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences

Volumn 56, Issue 12, 2001, Pages 1349-1353

  Zimmermann, Thomas J ^a   Muller, Thomas J J ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

METHANE;

CRYSTAL VIOLET; OXIDATIVE CONDITIONS; RADICAL CATIONS; STABLE SPECIES; TETRAKIS; TETRAMETHYL; UV/VIS ABSORPTIONS;

ANODIC OXIDATION;

EID: 0039149300     PISSN: 09320776     EISSN: None     Source Type: Journal    
DOI: 10.1515/znb-2001-1217     Document Type: Article

References (37)

1. a) D. A. Tomalia, A. M. Naylor, W. A. Goddard, Angew. Chem. 102, 119 (1990); Angew. Chem. Int. Ed. Engl. 29, 113 (1990);
2. a) D. A. Tomalia, A. M. Naylor, W. A. Goddard, Angew. Chem. 102, 119 (1990); Angew. Chem. Int. Ed. Engl. 29, 113 (1990);
3. b) C. J. Hawker, J. M. J. Fréchet, J. Am. Chem. Soc. 112, 7638 (1990);
4. c) A. J. Berresheim, M. Müller, K. Müllen, Chem. Rev. 99, 1747 (1999);
5. d) P. F. H. Schwab, M. D. Levin, J. Michl, Chem. Rev. 99, 1863 (1999).
6. For a very recent review on dendrimers, see e.g. M. Fischer F. Vögtle, Angew. Chem. 111, 934 (1999); Angew. Chem. Int. Ed. Engl. 38, 885 (1999)
7. For a very recent review on dendrimers, see e.g. M. Fischer F. Vögtle, Angew. Chem. 111, 934 (1999); Angew. Chem. Int. Ed. Engl. 38, 885 (1999)
8. For recent and significant contributions to the synthesis of tetraarylmethanes, see e.g.; a) L. M. Wilson, A. C. Griffin, J. Mater. Chem. 3, 991 (1993);
9. b) S. Sengupta, S. K. Sadhukhan, Tetrahedron Lett. 39, 1237 (1998);
10. c) S. Sengupta, S.K. Sadhukhan, Tetra Hedron Lett. 40, 9157 (1999);
11. d) O. Mongin, A. Gossauer, Tetrahedron 53, 6835 (1997);
12. e) U.-M. Wiesler, K. Müllen, Chem. Commun. 2293 (1999);
13. f) E. Galoppini, R. Gilardi, Chem. Commun., 173 (1999);
14. g) J. P. Novak, D. L. Feldheim, J. Am. Chem. Soc. 122, 3979 (2000);
15. h) W. J. Oldham (Jr)., R. J. Lachicolle, G. C. Bazan, J. Am. Chem. Soc. 120, 2987 (1998);
16. i)S. Wang, W. J. Oldham Jr., R. A. Hudack (Jr.), G. C. Bazan, J. Am. Chem. Soc. 122, 2987 (2000).
17. S. Eldin, J. F. Liebman, L. D. Reynolds, P. Dowd, Tetrahedron Lett. 33, 4525 (1992).
18. a) An Introduction to Molecular Electronics (M. C. Petty, M. R. Bryce, D. Bloor, Eds.), Oxford University Press, New York (1995);
19. b) for molecular materials in electronic and opto-electronic devices, see e.g. a special issue in Acc. Chem. Res. 32, issue 3 (1999).
20. For molecular solids as film transistors, see e.g.; a) H. E. Katz, J. Mater. Chem. 7, 369 (1997);
21. b) F. Garnier, Acc. Chem. Res. 32, 209 (1999);
22. c)J. Cornil, D. Beljonne, J.-P. Calbert, J.-L. Brédas, Adv. Mater. 13, 1053 (2001).
23. For molecular based electronics, see e.g.; d)J. M. Tour, Acc. Chem. Res. 33, 791 (2000);
24. e) M. A. Reed, J. M. Tour, Sci. Am. 282, 86 (2000);
25. f) H. E. Katz, Z. Bao. S. L. Gilat, Acc. Chem. Res. 34, 359 (2001);
26. g) F. Würthner, Angew. Chem. 113, 1069 (2001); Angew. Chem. Int. Ed. Engl. 40, 1037 (2001).
27. g) F. Würthner, Angew. Chem. 113, 1069 (2001); Angew. Chem. Int. Ed. Engl. 40, 1037 (2001).
28. T. J. Zimmermann, O. Freundel, R. Gompper, T. J. J. Müller, Eur. J. Org. Chem., 3305 (2000).
29. A. G. Giumanini, G. Chiavari, M. M. Musiani, P. Rossi, Synthesis, 743 (1980).
30. F. A. Neugebauer, H. Fischer, R. Bernhardt, Chem. Ber. 109, 2389 (1976).
31. J. Burfeindt, M. Patz, M. Müller, H. Mayr, J. Am. Chem. Soc. 120, 3629 (1998).
32. S. Akiyama, S. Nakatsuji, K. Nakashima, M. Watanabe, H. Nakazumi, J. Chem. Soc., Perkin Trans. 1, 3155 (1988).
33. T. Nagai, T. Shingaki, H. Yamada, Bull. Chem. Soc. Jpn. 50, 248 (1977).
34. For the formation of 7 and its products upon chemical oxidations of aryl bis(dimethylaminophenyl) carbinols or cations see, e.g.; a) J. Barek, A. Berka, L. Novakova, M. Matrka, Coll. Czech. Chem. Commun. 41, 3546 (1976);b) J. Barek, A. Berka, L. Novakova, Coll. Czech. Chem. Commun. 43, 1597 (1978);c)J. Barek, A. Berka, L. Novakova, Coll. Czech. Chem. Commun. 43, 1878 (1978).
35. For the formation of 7 and its products upon chemical oxidations of aryl bis(dimethylaminophenyl) carbinols or cations see, e.g.; a) J. Barek, A. Berka, L. Novakova, M. Matrka, Coll. Czech. Chem. Commun. 41, 3546 (1976);b) J. Barek, A. Berka, L. Novakova, Coll. Czech. Chem. Commun. 43, 1597 (1978);c)J. Barek, A. Berka, L. Novakova, Coll. Czech. Chem. Commun. 43, 1878 (1978).
36. For the formation of 7 and its products upon chemical oxidations of aryl bis(dimethylaminophenyl) carbinols or cations see, e.g.; a) J. Barek, A. Berka, L. Novakova, M. Matrka, Coll. Czech. Chem. Commun. 41, 3546 (1976);b) J. Barek, A. Berka, L. Novakova, Coll. Czech. Chem. Commun. 43, 1597 (1978);c)J. Barek, A. Berka, L. Novakova, Coll. Czech. Chem. Commun. 43, 1878 (1978).
37. st edition, VEB Deutscher Verlag der Wissenschaften, Berlin (2001).