Correlation of substituent effects and energy levels of the two lowest excited states of the azulenic chromophore

Organic Letters

Volumn 2, Issue 3, 2000, Pages 269-271

  Liu, Robert S H ^a   Muthyala, Rajeev S ^a   Wang, Xue Song ^a   Asato, Alfred E ^a   Wang, Peng ^b   Ye, Cheng ^b  

^a UNIVERSITY OF HAWAII   (United States)

^b INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000673441     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990324w     Document Type: Article

References (17)

1. (a) Heilbronner, E. Tetrahedron 1963, 19, supplement, 289-313.
2. (b) Michl, J.; Thulstrup, E. W. Tetrahedron 1976, 32, 205-209.
3. (a) Beer, M.; Longuet-Higgins, H. C. J. Chem. Phys. 1955, 23, 1390-1391.
4. (b) Viswath, G.; Kasha, M. J. Chem. Phys. 1956, 24, 574-577.
5. (c) Sidman, J. W.; McClure, D. S. J. Chem. Phys. 1956, 24, 757-763.
6. Bearpark, B. R.; Vreven, T. J. Am. Chem. Soc. 1996, 118, 169-175.
7. See, for example: Michl, J. Tetrahedron 1984, 40, 3845-3934.
8. Muthyala, R. S.; Liu, R. S. H. J. Fluorine Chem. 1998, 89, 173-175.
9. In the same vein, the red-shift of the 2-, 4-, 6-, and/or 8-cyanoazulenes has been attributed to selective lowering of the LUMO: Schmitt, S.; Baumgarten. M.; Simon, J.; Hafner, K. Angew. Chem., Int. Ed. 1998, 37, 1078-1081.
10. Compound 4 was prepared according to a literature procedure: Hafner, K.; Bernhard, C. Angew. Chem. 1957, 69, 533.
11. For absorption spectra of azulenes with other electron-withdrawing substituents, see: Dhingra, R. C.; Poole, J. A. Chem. Phys. Lett. 1968, 2, 108-109.
12. For recent calculations on other azulenic compounds, see: Wang, P.; Zhu, P.; Ye, C.; Asato, A. E.; Liu, R. S. H. J. Phys. Chem. 1999, 103, 7076-7082.
13. (a) Asato, A. E.; Li, X.-Y.; Mead, D.; Patterson, G. L. M.; Liu, R. S. H. J. Am. Chem. Soc. 1990, 112, 7398-7399.
14. (b) Liu, R. S. H.; Krogh, E.; Li, X.-Y.; Mead, D.; Colmenares, L. U.; Thiel, J. R.; Ellis, J.; Wong, D.; Asato, A. E. Photochem. Photobiol. 1993, 58, 701-705.
15. (a) Nakanishi, K.; Derguini, F.; Rao, V. J.; Zarrilli, G.; Okabe, M.; Lien, T.; Johnson, R. Pure Appl. Chem. 1989, 61, 361-364.
16. (b) Zarrilli, G. R. Ph.D. Thesis, Columbia University, 1984.
17. For the enal, only data of the guaiazulene analogues of 5 are available in the literature.