Metal-ligand versus metal-metal redox chemistry: Thallium(I)-induced synthesis of 4,9-diaminoperylenequinone-3,10-diimine derivatives

Angewandte Chemie - International Edition

Volumn 37, Issue 13-14, 1998, Pages 1948-1952

  Hellmann, Konrad W ^a   Galka, Christian H ^a   Rüdenauer, Ina ^a   Gade, Lutz H ^a   Scowen, Ian J ^b   McPartlin, Mary ^b  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b LONDON METROPOLITAN UNIVERSITY   (United Kingdom)

Author keywords

Dyes; Indium; Mixed valent compounds; Redox chemistry; Thallium

Indexed keywords

EID: 0032479751     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980803)37:13/14<1948::AID-ANIE1948>3.0.CO;2-X     Document Type: Article

References (37)

1. a) Unkonventionelle Wechselwirkungen in der Chemie metallischer Elemente (Ed.: B. Krebs), VCH, Weinheim, 1992;
2. b) P. Pyykkö, Chem. Rev. 1997, 97, 597.
3. a) C. Janiak, R. Hoffmann, J. Am. Chem. Soc. 1990, 112, 5024;
4. b) K. W. Klinkhammer, S. Henkel, J. Organomet. Chem. 1994, 480, 167;
5. c) W. Uhl, S. U. Keimling, K. W. Klinkhammer, W. Schwarz, Angew. Chem. 1997, 109, 64; Angew. Chem. Int. Ed. Engl. 1997, 36, 64.
6. c) W. Uhl, S. U. Keimling, K. W. Klinkhammer, W. Schwarz, Angew. Chem. 1997, 109, 64; Angew. Chem. Int. Ed. Engl. 1997, 36, 64.
7. d) M. Veith, A. Spaniol, J. Pöhlmann, F. Gross, V. Huch, Chem. Ber. 1993, 126, 2625.
8. a) K. W. Hellmann, L. H. Gade, I. J. Scowen, M. McPartlin, Chem. Commun. 1996, 2515;
9. b) K. W. Hellmann, L. H. Gade, R. Fleischer, D. Stalke, ibid. 1997, 527;
10. c) K. W. Hellmann, L. H. Gade, R. Fleischer, T. Kottke, Chem. Eur. J. 1997, 3, 1801.
11. a) K. W. Hellmann, L. H. Gade, A. Steiner, D. Stalke, F. Möller, Angew. Chem. 1997, 109, 99; Angew. Chem. Int. Ed. Engl. 1997, 36, 160;
12. a) K. W. Hellmann, L. H. Gade, A. Steiner, D. Stalke, F. Möller, Angew. Chem. 1997, 109, 99; Angew. Chem. Int. Ed. Engl. 1997, 36, 160;
13. b) S. Henkel, K. W. Klinkhammer, W. Schwarz, ibid. 1994, 106, 721 and 1994, 33, 681;
14. b) S. Henkel, K. W. Klinkhammer, W. Schwarz, ibid. 1994, 106, 721 and 1994, 33, 681;
15. c) W. Uhl, ibid. 1993, 105, 1449 and 1993, 32, 1386.
16. c) W. Uhl, ibid. 1993, 105, 1449 and 1993, 32, 1386.
17. a) E. Steckan in Organic Electrochemistry (Eds.: H. Lund, M. M. Baizer), 3rd ed., Dekker, New York, 1991, p. 581;
18. b) M. Schmittel, A. Burghart, Angew. Chem. 1997, 109, 2658; Angew. Chem. Int. Ed. Engl. 1997, 36, 2550;
19. b) M. Schmittel, A. Burghart, Angew. Chem. 1997, 109, 2658; Angew. Chem. Int. Ed. Engl. 1997, 36, 2550;
20. c) R. L. Hand, R. F. Nelson, J. Am. Chem. Soc. 1974, 96, 850.
21. K. W. Hellmann, C. H. Galka, L. H. Gade, A. Steiner, D. S. Wright, T. Kottke, D. Stalke, Chem. Commun. 1998, 549.
22. [10b] For programs, see reference [19].
23. 6 ions with In-In distances ranging between 2.624 and 2.689 Å.
24. 6 ions with In-In distances ranging between 2.624 and 2.689 Å.
25. max = 444 nm, lgε = 4.7) involving the N substituents.
26. 2) = 0.981 for 490 parameters. For programs, see reference [19]. b) Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-101 183. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: (+49) 1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
27. A. Zinke, W. Hirsch, E. Brozek, Monatsh. Chem. 1929, 51, 205.
28. a) J. W. Lown, Can. J. Chem. 1997, 75, 99;
29. b) M. Wainright, Chem. Soc. Rev. 1996, 351.
30. C. Näther, Dissertation, Universität Frankfurt, 1994, cited in reference [14].
31. H. Bock, C. Näther, Z. Havlas, J. Am. Chem. Soc. 1995, 117, 3870.
32. W.-S. Chen, Y.-T. Chen, X.-Y. Wan, E. Friedrichs, H. Puff, E. Breitmaier, Liebigs Ann. Chem. 1981, 1880.
33. F. Graser, E. Hädicke,. Liebigs Ann. Chim. 1980, 1994.
34. E. Hädicke, F. Graser, Acta Crystallogr. C 1986, 42, 189.
35. 2 were unsuccessful. The use of spin-trapping reagents was precluded by the extremely high reactivity of 4, which thermally and unspecifically reacted with the trapping agents prior to its thermolysis. Attempts to detect radical intermediates by NMR spectroscopy at different field strengths and temperatures through observation of a CIDNP effect were equally unsuccessful. These results either indicate the absence of a free radical species in the coupling reaction or, alternatively, their short-lived nature.
36. SHELXTL 5.03, Siemens Analytical X-Ray Instruments Inc., 1994, Madison WI, USA.
37. K. W. Hellmann, L. H. Gade, Verfahrenstechnik 1997, 31 (5), 70.