Axially chiral bichromophoric fluorescent dyes

Journal of Organic Chemistry

Volumn 76, Issue 3, 2011, Pages 990-992

  Langhals, Heinz ^a   Hofer, Alexander ^a   Bernhard, Stefan ^b   Siegel, Jay S ^c   Mayer, Peter ^a  

^a UNIVERSITY OF MUNICH   (Germany)

^b CARNEGIE MELLON UNIVERSITY   (United States)

^c UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORESCENT DYES;

9 (1 HEXYLHEPTYL) 2 BENZOPYRANO[6',5',4':1',5,6]ANTHRA[2,1,9:DEF]ISOQUINOLINE 1,3,8,10 TETRAONE; FLUORESCENT DYE; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CHROMATOPHORE; PHOTOCHEMISTRY;

EID: 79851476207     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo102254a     Document Type: Article

References (27)

1. Mislow, K.; Rutkin, P.; Lazarus, A. K. J. Am. Chem. Soc. 1957, 79, 2974-2975.
2. Jones, W. M.; Wilson, J. W. Tetrahedron Lett. 1965, 21, 1587- 1592.
3. Mislow, K. Angew. Chem. 1958, 70, 638-689.
4. The author J.S.S. supports the technical aspects of this work fully but disagrees with the use of terminology like "axial chirality";
5. see: Mislow, K.; Siegel, J. J. Am. Chem. Soc. 1984, 106, 3319-3328.
6. Cozzi, F.; Siegel, J. S. Org. Biomol. Chem. 2005, 3, 4296-4298. The author H.L. emphasizes that terms such as "axial chirality" or the "asymmetric carbon atom" are no more than useful chemical models for helical arrangements of electrons induced by the nuclear framework. Elements of symmetry of polyatomic molecules in solution are in no way verified in reality because of zero point vibrations and many other effects where, for example, phenomenologically achiral molecules form either fast equilibria of racemization or reach states with rotary alternating axes.
7. Bachrach, S. M. Computational Organic Chemistry; John Wiley & Sons: New York, 2007; pp 394-395.
8. Villar, R.; Gil, M. J.; Garcia, J. I.; Martinez-Merino, V. J. Comput. Chem. 2005, 26, 1347-1358.
9. Chem. Abstr. 2005, 143, 410902.
10. We thank Prof. R. de Vivie-Riedle and Dr. H.-U. Wagner for helpful discussions.
11. Reviews: (aLanghals, H. Helv. Chim. Acta 2005, 88, 1309-1343.
12. Langhals, H. Heterocycles 1995, 40, 477-500.
13. Johansson, L. B.-Å.; Langhals,H. Spectrochim.Acta 1991, 47A, 857-861.
14. Kaiser, H.; Lindner, J.; Langhals, H. Chem. Ber 1991, 124, 529-535.
15. Kelber, J.; Bock, H.; Thiebaut, O.; Grelet, E.; Langhals, H. Eur. J. Org. Chem. 2010, DOI: 10.1002/ejoc.201001346.
16. Holser, E. F. J. Ind. Eng. Chem. 1936, 28, 691-698.
17. Chem. Abstr. 1936, 30, 35957.
18. Ullock, D. S.; Gaffert, G. A.; Konz, P. R.; Brown, G. G. Trans. Am. Inst. Chem. Eng. 1936, 32, 73-86.
19. Chem. Abstr. 1937, 31, 43447.
20. Rathur, M. A. J. Br. J. Appl. Phys. 1964, 15, 437-438.
21. Chem. Abstr, 1966, 64, 81864.
22. Langhals, H.; Gold, J. Liebigs Ann./Recl. 1997, 1151-1153.
23. Tsumatori, H.; Nakashima, T.; Kawai, T. Org. Lett. 2010, 12, 2362-2365.
24. Tsumatori, H.; Nakashima, T.; Yuasa, J.; Kawai, T. Synth. Met. 2009, 159, 952-954.
25. Kawai, T.; Kawamura, K.; Tsumatori, H.; Ishikawa, M.; Naito, M.; Fujiki, M.; Nakashima, T. ChemPhysChem 2007, 8, 1465-1468.
26. Pritchard, B.; Autschbach, J. ChemPhysChem 2010, 11, 2409-2415.
27. Oyler, K. D.; Coughlin, F. J.; Bernhard, S. J. Am. Chem. Soc. 2007, 129, 210-217.