Intramolecular electronic interactions between nonconjugated arene and quinone chromophores

Journal of the American Chemical Society

Volumn 132, Issue 25, 2010, Pages 8581-8592

  Jansen, Georg ^a   Kahlert, Björn ^a   Klärner, Frank Gerrit ^a   Boese, Roland ^a   Bläser, Dieter ^a  

^a UNIVERSITY OF DUISBURG ESSEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION; ANTHRACENE; AROMATIZATION; BENZENE; CALCULATIONS; CHARGE TRANSFER; CHROMOPHORES; COLOR; ELECTRONIC PROPERTIES; ION EXCHANGE; KETONES; MASS TRANSFER; PHENOLS;

AB INITIO CALCULATIONS; ABSORPTION BAND; AROMATIC UNITS; BATHOCHROMIC SHIFT; CHARGE TRANSFER STATE; COLOR CHANGES; CONFIGURATION INTERACTIONS; DEGREE OF MIXING; ELECTRONIC INTERACTIONS; EXPERIMENTAL SPECTRA; HOMOCONJUGATION; INTRA-MOLECULAR CHARGE TRANSFER; MOLECULAR CLIPS; NONCONJUGATED; ORANGE-RED; ORBITALS; P-BENZOQUINONE; QUANTUM CHEMICAL; THROUGH-SPACE INTERACTION; UV/VIS SPECTRA; VISIBLE RANGE;

NAPHTHALENE;

1,4 BENZOQUINONE; ANTHRACENE; DUROQUINONE; HYDROQUINONE; NAPHTHALENE; POLYCYCLIC AROMATIC HYDROCARBON; QUINONE DERIVATIVE; ANTHRACENE DERIVATIVE; AROMATIC HYDROCARBON; BENZOQUINONE; BENZOQUINONE DERIVATIVE; NAPHTHALENE DERIVATIVE;

ARTICLE; CHROMATOPHORE; CONTROLLED STUDY; CRYSTAL STRUCTURE; ELECTRONICS; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY; CHEMICAL STRUCTURE; CHEMISTRY; COLOR; CONFORMATION; ELECTRON; QUANTUM THEORY; ULTRAVIOLET SPECTROPHOTOMETRY;

ANTHRACENES; BENZOQUINONES; COLOR; ELECTRONS; HYDROCARBONS, AROMATIC; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NAPHTHALENES; QUANTUM THEORY; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 77953903102     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja910362j     Document Type: Article

References (46)

1. "Through-space", "through-bond" interactions
2. Hoffmann, R., Heilbronner, E., and Gleiter, R. J. Am. Chem. Soc. 1970, 92, 706-707
3. Hoffmann, R. Acc. Chem. Res. 1971, 4, 1-9
4. Filipescu, N., Minn, F. L., and Thomas, A. V. J. Chem. Soc., Perkin Trans. 2 1972, 1697-1702
5. Haselbach, E., Neuhaus, L., Johnson, R. P., Houk, K. N., and Paddon-Row, M. N. Helv. Chim. Acta 1982, 65, 1743-1751
6. Jordan, K. D. and Paddon-Row, M. N. Chem. Rev. 1992, 92, 395-410
7. Electron transfer through DNA and peptides
8. Giese, B. Bioorg. Med. Chem. 2006, 4, 6139-6143
9. Breeger, S., von Meltzer, M., Hennecke, U., and Carell, T. Chem.-Eur. J. 2006, 12, 6469-6477
10. Boussicault, F. and Robert, M. Chem. Rev. 2008, 108, 2622-2645
11. Elias, B., Genereux, J. C., and Barton, J. K. Angew. Chem., Int. Ed. 2008, 47, 9067-9070
12. Ghosh, A., Joy, A., Schuster, G. B., Douki, T., and Cadet, J. Org. Biomol. Chem. 2008, 6, 916-928
13. Caraballo-Martinez, N., del Rosario Colorado Heras, M., Blazquez, M. M., Barcina, J. O., Martinez, A. G., and del Rosario Torres Salvador, M. Org. Lett. 2007, 9, 2943-2946
14. Bell, T. D. M., Stefan, A., Lemaur, V., Bernhardt, S., Muellen, K., Cornil, J., Beljonne, D., Hofkens, J., Van der Auweraer, M., and De Schryver, F. C. Photochem. Photobiol. Sci. 2007, 6, 406-415
15. Kobayashi, T. and Kobayashi, S. Eur. J. Org. Chem. 2002, 2066-2073
16. Zimmerman, H. E. and McKelvey, R. D. J. Am. Chem. Soc. 1971, 93, 3638-3645
17. Oevering, H., Paddon-Row, M. N., Heppener, M., Oliver, A. M., Cotsaris, E., Verhoeven, J. W., and Hush, N. S. J. Am. Chem. Soc. 1987, 109, 3258-3269
18. Paddon-Row, M. N. Acc. Chem. Res. 1994, 27, 18-25
19. Goldsmith, R. H., Vura-Weis, J., Scott, A. M., Borkar, S., Sen, A., Ratner, M. A., and Wasielewski, M. R. J. Am. Chem. Soc. 2008, 130, 7659-7669
20. Cappel, D., Tüllmann, S., Krapp, A., and Frenking, G. Angew. Chem., Int. Ed. 2005, 44, 3617-3620
21. Fernandez, I. and Frenking, G. Chem.-Eur. J. 2006, 12, 3617-3629
22. Heilbronner, E. and Schmelzer, A. Helv. Chim. Acta 1975, 58, 936-967
23. Martin, H.-D. and Mayer, B. Angew. Chem., Int. Ed. 1983, 22, 283-314
24. Houk, K. N., Rondan, N. G., Paddon-Row, M. N., Jefford, C. W., Thanh Huy, P., Burrow, P. D., and Jordan, K. D. J. Am. Chem. Soc. 1983, 105, 5563-5568
25. Iwamura, H. and Makino, K. J. Chem. Soc., Chem. Commun. 1978, 720-721
26. Vischer, E. B. J. Chem. Soc. 1953, 815-820
27. Flaig, W. and Salfeld, J.-C. Justus Liebigs Ann. Chem. 1958, 618, 117-139
28. Attemps to synthesize the anti-configured anthracene clip for a comparison with clip 1 failed presumably because of the low solubility of the tetrabromoderivative of 9 which did not react with n -butyllithium and furan. Kahlert, B. Dissertation, University of Duisburg-Essen, 2005.
29. Klärner, F.-G., Kahlert, B., Boese, R., Blaeser, D., Juris, A., and Marchioni, F. Chem.-Eur. J. 2005, 11, 3363-3374
30. Klärner, F.-G., Panitzky, J., Bläser, D., and Boese, R. Tetrahedron 2001, 3673-3687
31. Bartlett, P. D. and Wallbillich, G. E. H. J. Am. Chem. Soc. 1969, 91, 409-414
32. Meinwald, J. and Wiley, G. A. J. Am. Chem. Soc. 1958, 80, 3667-3671
33. Vaughan, W. R. and Yoshimine, M. J. Org. Chem. 1957, 22, 7-12
34. Cava, M. P. and Napier, D. R. J. Am. Chem. Soc. 1957, 79, 1701-1709
35. Cava, M. P. and Shirley, R. L. J. Am. Chem. Soc. 1960, 82, 654-656
36. Paddon-Row, M. N., Patney, H. K., and Harish, K. Synthesis 1986, 328-330
37. Bürgi, H.-B., Baldridge, K. K., Hardcastle, K., Frank, N. L., Gantzel, P., Siegel, J. S., and Ziller, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1454-1456
38. Frank, N. L., Baldridge, K. K., and Siegel, J. S. J. Am. Chem. Soc. 1995, 117, 2102-2103
39. Frank, N. L., Baldridge, K. K., Gantzel, P., and Siegel, J. S. Tetrahedron Lett. 1995, 36, 4389-4392
40. Rathore, R., Lindemann, S. V., Kumar, A. S., and Kochi, J. K. J. Am. Chem. Soc. 1998, 120, 6012-6018
41. Cardullo, F., Giuffrida, D., Kohnke, F. H., Raymo, F. M., Stoddart, J. F., and Williams, D. J. Angew. Chem., Int. Ed. Engl. 1996, 35, 339-341
42. Christiansen, O., Koch, H., and Jørgensen, P. Chem. Phys. Lett. 1995, 243, 409-418
43. Dunning, T. H., Jr. J. Chem. Phys. 1989, 90, 1007-1023
44. Hättig, C. and Weigend, F. J. Chem. Phys. 2000, 113, 5154-5161
45. Hättig, C. and Köhn, A. J. Chem. Phys. 2002, 117, 6939-6951
46. Weber, J., Malsch, K., and Hohlneicher, G. Chem. Phys. Lett. 2001, 264, 275-318