Chiral tri- and pentamethinium cyanine dyes with 1,2,3,4-tetrahydro-6-methylquinolyl end groups: UV/Vis and CD spectroscopy and structure correlations

Liebigs Annales

Volumn , Issue 11, 1996, Pages 1823-1831

  Buß, Volker ^a   Ulbrich, Dagmar ^a   Reichardt, Christian ^b  

^a UNIVERSITY OF DUISBURG ESSEN   (Germany)

^b PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

Chirality; Circular dichroism; Cyanine dyes, chiral; Dyes

Indexed keywords

EID: 33748912165     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199619961116     Document Type: Article

References (26)

1. [5].
2. R. Raue, "Methine Dyes and Pigments" in Ullmann's Encyclopedia of Industrial Chemistry, 5th ed., VCH, Weinheim, 1990, vol. A16, p. 487-534.
3. H. Kuhn, Helv. Chim. Acta 1948, 31, 1441-1455.
4. W. König, Z. Angew. Chem. 1928, 41, 615-616.
5. C. Reichardt, J. Phys. Org. Chem. 1995, 8, 761-773.
6. R. Janoschek (Ed.), Chirality - From Weak Bosons to the α-Helix, Springer, Berlin - Heidelberg - New York, 1992.
7. [7a] N. Purdie, H. G. Brittain (Eds.), Analytical Applications of Circular Dichroism, Elsevier, Amsterdam, 1994.
8. [7b] K. Nakanishi, N. Berova, R. W. Woody (Eds.), Circular Dichroism - Principles and Applications, VCH, Weinheim, 1994.
9. C. Payrastre, N. Obaya, Y. Madaule, J.-G. Wolf, Tetrahedron Lett. 1994, 35, 3059-3062.
10. C. Reichardt, U. Budnik, Chem. Ber. 1990, 123, 2023-2030.
11. L. Eggers, V. Buß, G. Henkel, Angew. Chem. 1996, 108, 973-975;
12. Angew. Chem. Int. Ed. Engl. 1996, 35, 870-872.
13. G. Snatzke, "Chiroptical Properties of Organic Compounds: Chirality and Sector Rules" in Optical Activity and Chiral Discrimination, (Ed.: S. F. Mason), Reidel, Dordtrecht, 1978, pp. 25-41.
14. E. Charney, The Molecular Basis of Optical Activity, Wiley, New York, 1979.
15. N. Harada, K. Nakanishi, Circular Dichroic Spectroscopy - Exciton Coupling in Organic Stereochemistry, University Science Books, Mill Valley, 1983.
16. [14a] C. Reichardt, K. Harms, M. Kinzel, G. Schäfer, J. Stein, S. Wocadlo, Liebigs Ann. 1995, 317-327.
17. [14b] C. Reichardt, J. Stein, unpublished results;
18. cf. J. Stein, Dissertation, University of Marburg, 1996.
19. J. E. Crooks, The Spectrum in Chemistry, Academic Press, London, 1978, pp. 155-184.
20. V. Prelog, G. Helmchen, Angew. Chem. 1982, 94, 614-631;
21. Angew. Chem. Int. Ed. Engl. 1982, 21, 567-583.
22. J. J. P. Stewart, Mopac 7.0, public domain copy, QCPE, 1991.
23. We thank Dr. Kolster for these calculations.
24. M. Speis, J. Messinger, N. Heuser, V. Buß, "Konformationsanalyse chiraler Verbindungen: Eine UV-Bibliothek zur Berechnung von Rotationshyperflächen", in Software-Entwicklung in der Chemie 3, (Ed.: G. Gauglitz), Springer, Berlin, Heidelberg, New York, 1989, pp. 387-395. CNDO/S was used in the standard version described in this report. The CI part was restricted to 100 singly excited states.
25. G. Snatzke, "Chiroptical Properties of Organic Compounds: Some Applications to Unsaturated Systems" in Optical Activity and Chiral Discrimination, (Ed.: S. F. Mason), Reidel, Dordrecht, 1978, pp. 387-395.
26. V. Buß, K. Kolster, Chem. Phys. 1996, 203, 309-316.