Rapid access to unusual solid-state luminescent merocyanines by a novel one-pot three-component synthesis

Organic Letters

Volumn 13, Issue 10, 2011, Pages 2556-2559

  Muschelknautz, Christian ^a   Frank, Walter ^a   Müller, Thomas J J ^a  

^a HEINRICH HEINE UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79956132250     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200655s     Document Type: Article

References (37)

1. Functional Organic Materials; Müller, T. J. J., Bunz, U. H. F., Eds.; WILEY-VCH: Weinheim, 2007.
2. Hamer, F. M. The Cyanine Dyes and Related Compounds; Interscience: New York, London, 1964.
3. Mishra, A.; Behera, R. K.; Behera, P. K.; Mishra, B. K.; Behera, G. B. Chem. Rev. 2000, 100, 1973-2011
4. Kulinich, A. V.; Ishchenko, A. A. Russ. Chem. Rev. 2009, 78, 141-164
5. Peng, X. Z. Y.; Carroll, S.; Geise, H. J.; Peng, B.; Dommisse, R.; Esmansc, E.; Carleer, R. J. Mater. Chem. 1996, 6, 1325-1333
6. Shirinian, V. Z.; Shimkin, A. A. Top. Heterocycl. Chem. 2008, 14, 75-105
7. Kovtun, Y. P.; Prostota, Y. O.; Shandura, M. P.; Poronik, Y. M.; Tolmachev, A. I. Dyes Pigm. 2004, 60, 215-221
8. Kovtun, Y. P.; Prostota, Y. O.; Tolmachev, A. I. Dyes Pigm. 2003, 58, 83-91
9. Yagi, S.; Maeda, K.; Nakazumi, H. J. Mater. Chem. 1999, 9, 2991-2997
10. Kay, A. J.; Woolhouse, A. D.; Gainsford, G. J.; Haskell, T. G.; Barnes, T. H.; McKinnie, I. T.; Wyss, C. P. J. Mater. Chem. 2001, 11, 996-1002
11. Würthner, F. Synthesis 1999, 2103-2113
12. Würthner, F.; Yao, S. J. Org. Chem. 2003, 68, 8943-8949
13. Yao, S.; Beginn, U.; Gress, T.; Lysetska, M.; Würthner, F. J. Am. Chem. Soc. 2004, 126, 8336-8346
14. For diversity-oriented syntheses of chromophores, see e.g.: Müller, T. J. J. In Functional Organic Materials. Syntheses, Strategies, and Applications; Wiley-VCH: Weinheim, 2007; pp 179-223.
15. Müller, T. J. J.; D'Souza, D. M. Pure Appl. Chem. 2008, 80, 609-620
16. Yi, C.; Blum, C.; Liu, S.-X.; Frei, G.; Neels, A.; Stoeckli-Evans, H.; Leutwyler, S.; Decurtins, S. Tetrahedron 2008, 40, 9437-9441
17. For combinatorial syntheses of chromophores, see e.g.: Samanta, A.; Vendrell, M.; Dasa, R.; Chang, Y.-T. Chem. Commun. 2010, 46, 7406-7408
18. Vendrell, M.; Lee, J.-S.; Chang, Y.-T. Curr. Opin. Chem. Biol. 2010, 14, 383-389
19. Main, M.; Snaith, J. S.; Meloni, M. M.; Jauregui, M.; Sykes, D.; Faulkner, S.; Kenwright, A. M. Chem. Commun. 2008, 5212-5214
20. Briehn, C. A.; Bäuerle, P. Chem. Commun. 2002, 1015-1023
21. Briehn, C. A.; Schiedel, M.-S.; Bonsen, E. M.; Schuhmann, W.; Bäuerle, P. Angew. Chem., Int. Ed. 2001, 40, 4680-4683
22. Willy, B.; Müller, T. J. J. Curr. Org. Chem. 2009, 13, 1777-1790
23. Willy, B.; Müller, T. J. J. ARKIVOC 2008, Part I, 195-208.
24. D'Souza, D. M.; Kiel, A.; Herten, D. P.; Müller, T. J. J. Chem.-Eur. J. 2008, 14, 529-547
25. D'Souza, D. M.; Rominger, F.; Müller, T. J. J. Angew. Chem., Int. Ed. 2005, 44, 153-158
26. Braun, R. U.; Müller, T. J. J. Synthesis 2004, 2391-2406
27. Willy, B.; Dallos, T.; Rominger, F.; Schönhaber, J.; Müller, T. J. J. Eur. J. Org. Chem. 2008, 4796-4805
28. Willy, B.; Müller, T. J. J. Eur. J. Org. Chem. 2008, 4157-4168
29. D'Souza, D. M.; Muschelknautz, C.; Rominger, F.; Müller, T. J. J. Org. Lett. 2010, 3364-3367
30. Karpov, A. S.; Müller, T. J. J. Org. Lett. 2003, 5, 3451-3454
31. Karpov, A. S.; Müller, T. J. J. Synthesis 2003, 2815-2826
32. For the addition of methylene active compounds to aryl ethynyl ketones, see e.g.: Johnson, A. W. J. Chem. Soc. 1947, 1626-1631
33. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC-816762 (6b) and -816763 (7b). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Fax: + 44-1223/336-033; E-mail: deposit@ccdc.cam.ac.uk).
34. Reichardt, C. Angew. Chem., Int. Ed. Engl. 1979, 18, 98-110
35. Lippert, E. Z. Elektrochem. 1957, 61, 962-975
36. Mataga, N.; Kaifu, Y.; Koizumi, M. Bull. Chem. Soc. Jpn. 1956, 29, 465-470
37. Franco, L.; Pasimeni, L.; Ponterini, G.; Ruzzi, M.; Serge, U. Phys. Chem. Chem. Phys. 2001, 3, 1736-1742