Chiral discrimination in photochromic helicenes

Journal of the American Chemical Society

Volumn 127, Issue 20, 2005, Pages 7272-7273

  Wigglesworth, Tony J ^a   Sud, David ^a   Norsten, Tyler B ^a   Lekhi, Vikram S ^a   Branda, Neil R ^a  

^a SIMON FRASER UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALICYCLIC COMPOUND; CYCLOPENTENE DERIVATIVE; HELICENE DERIVATIVE; NAPHTHALENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CRYSTAL STRUCTURE; DEVICE INFECTION; LIQUID CRYSTAL; REACTION ANALYSIS; RING CLOSING METATHESIS; RING OPENING; STRUCTURE ANALYSIS;

EID: 19744367411     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja050190j     Document Type: Article

References (30)

1. Feringa, B. L. Molecular Switches; Wiley-VCH: Weinheim, Germany, 2001.
2. van Delden, R. A.; Mecca, T.; Rosini, C.; Ferinaa, B. L. Chem.-Eur. J. 2004, 10, 61.
3. Pieraccini, S.; Masiero, S.; Spada, G. P.; Gottarelli, G. Chem. Commun. 2003, 598.
4. Maly, K. E.; Wand, M. D.; Lemieux, R. P. J. Am. Chem. Soc. 2002, 124, 7898.
5. Uchida, K.; Kawai, Y.; Shimizu, Y.; Vill, V.; Irie, M. Chem. Lett. 2000, 654.
6. Mureuly, E.; Horsten, T. B.; Branda, N. R. Angew. Chem., Int. Ed. 2001, 40, 1752.
7. Irie, M. In Organic Pholochromic and Thermochromic Compounds; Crano, J. C., Gualiemetti, R. J., Eds.; Plenum: New York, 1999; Vol. 1, p 207.
8. Irie, M. Chem. Rev. 2000, 100, 1685.
9. Irie, M. In Molecular Switches; Ferinaa, B. L., Ed.; Wiley-VCH: Weinheim, Germany, 2001; p 37.
10. Tian, H.; Yang, S. Chem. Soc. Rev. 2004, 33, 85.
11. de Jong, J. J. D.; Lucas, L. N.; Kellogg, R. M.; van Esch, J. H.; Feringa, B. L. Science 2004, 304, 278.
12. Takeshita, M.; Yamato, T. Chem. Lett. 2004, 33, 844.
13. Kose, M.; Shinoura, M.; Yokoyama, Y.; Yokoyama, Y. J. Org. Chem. 2004, 69, 8403.
14. Yamamoto, S.; Matsuda, K.; Irie, M. Org. Lett. 2003, 5, 1769.
15. Yamaguchi, T.; Inagawa, T.; Nakazumi, H.; Irie, S.; Irie, M. J. Mater. Chem. 2001, 11, 2453.
16. Yamaguchi, T.; Uchida, K.; Irie, M. J. Am. Chem. Soc. 1997, 119, 6066.
17. Katz, T. J. Angew. Chem., Int. Ed. 2000, 39, 1921.
18. Higuchi, H.; Ohta, E.; Kawai, H.; Fujiwara, K.; Tsuji, T.; Suzuki, T. J. Org. Chem. 2003, 68, 6605.
19. Zahn, S.; Canary, J. W. Science 2000, 288, 1404.
20. Beer, G.; Niederalt, C.; Grimme, S.; Daub, J. Angew. Chem., Int. Ed. 2000, 39, 3252.
21. Goto, H.; Yashima, E. J. Am. Chem. Soc. 2002, 124, 7943.
22. Huck, N. P. M.; Jager, W. F.; de Lange, B.; Feringa, B. L. Science 1996, 273, 1686.
23. Norsten, T. B.; Peters, A.; McDonald, R.; Wang, M.; Branda, N. R. J. Am. Chem. Soc. 2001, 123, 7447.
24. Performed using a CHIRALCEL-OD column (1.0 mL/min, hexanes). This column has been successfully used to separate the enantiomers of compound B and other thiahelicenes. See ref 14 and Supporting Information for details.
25. Semiempirical calculations (AM1) using Spartan '02 from Wavefuntion, Inc. estimate that the M-2 stereoisomer is ∼16 kcal/mol more stable than the P-2 stereoisomer.
26. It is accepted that the trends in the CD spectra are consistent for a series of compounds of similar structure and chirality. M-Helicenes typically exhibit positive Δε values in the higher-energy regions and negative values at the lower-energy regions of the CD spectra. Wachsmann, C.; Weber, E.; Czugler, M.; Seichter, W. Eur. J. Org. Chem. 2003, 2863.
27. Caronna, T.; Sinisi, R.; Catellani, M.; Luzzati, S.; Abbate, S.; Lonahi, G. Synth. Met. 2001, 119, 79.
28. Groen, M. B.; Wvnbera, H. J. Am. Chem. Soc. 1971, 93, 2968.
29. Berova, N.; Nakanishi, K.; Woody, R. W. Circular Dichroism. Principles and Applications; Wiley-VCH: Weinheim, Germany, 2000; Chapter 12.
30. The arm of isomer 1 does not show Cotton effects. The coexistence of four equal-energy conformers is predicted by molecular modeling (Spartan AM1).