Dynamic control and amplification of molecular chirality by circular polarized light

Science

Volumn 273, Issue 5282, 1996, Pages 1686-1688

  Huck, Nina P M ^a   Jager, Wolter F ^a   De Lange, Ben ^a   Feringa, Ben L ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

AMPLIFICATION; ANISOTROPY; DOPING (ADDITIVES); IRRADIATION; LIGHT MODULATION; LIGHT POLARIZATION; MOLECULAR STRUCTURE; NEMATIC LIQUID CRYSTALS; OPTICAL DATA STORAGE; OPTICAL MATERIALS; OPTICAL PROPERTIES; PHOTOCHEMICAL REACTIONS;

CHIRAL MESOSCOPIC PHASE; CIRCULAR DICHROISM; CIRCULAR POLARIZED LIGHT; DYNAMIC CONTROL; ENANTIOMERS; HELICAL ALKENE; MOLECULAR CHIRALITY; PHOTOISOMERIZATION; PHOTORESOLUTION;

ORGANIC COMPOUNDS;

ARTICLE; CHIRALITY; CIRCULAR DICHROISM; DYNAMICS; ENANTIOMER; IRRADIATION; ISOMERISM; NONHUMAN; POLARIZATION; PRIORITY JOURNAL; PROTEIN STABILITY; SURFACE PROPERTY;

EID: 10144261883     PISSN: 00368075     EISSN: None     Source Type: Journal    
DOI: 10.1126/science.273.5282.1686     Document Type: Article

References (26)

1. J.-M. Lehn, Supramolecular Chemistry (VCH, Weinheim, 1995).
2. P. Ball and L. Garwin, Nature 355, 761 (1992).
3. B. L. Feringa, W. F. Jager, B. de Lange, Tetrahedron 49, 8267 (1993); I. Willner and B. Willner, Adv. Mater. 17, 587 (1995). For a pertinent example of a stable molecular switch, see S. H. Kawai, S. L. Gilat, J.-M. Lehn, J. Chem. Soc. Chem. Commun. 8, 1011 (1994).
4. B. L. Feringa, W. F. Jager, B. de Lange, Tetrahedron 49, 8267 (1993); I. Willner and B. Willner, Adv. Mater. 17, 587 (1995). For a pertinent example of a stable molecular switch, see S. H. Kawai, S. L. Gilat, J.-M. Lehn, J. Chem. Soc. Chem. Commun. 8, 1011 (1994).
5. B. L. Feringa, W. F. Jager, B. de Lange, Tetrahedron 49, 8267 (1993); I. Willner and B. Willner, Adv. Mater. 17, 587 (1995). For a pertinent example of a stable molecular switch, see S. H. Kawai, S. L. Gilat, J.-M. Lehn, J. Chem. Soc. Chem. Commun. 8, 1011 (1994).
6. For switching process of diastereoisomers with unpolarized light, see W. F. Jager et al., Angew. Chem. Int. Ed. Engl. 34, 348 (1995).
7. For a brief review of chiroptical molecular switches based on bistable nonracemic materials, see B. L. Feringa, N. P. M. Huck, A. M. Schoevaars, Adv. Mater., in press.
8. Discriminative interactions of CPL with racemic materials have been proposed in the context of the origin of chirality [S. L. Milla and L. E. Orgel, The Origin of Life on the Earth (Prentice-Hall. Englewood Cliffs, NJ, 1974); W. A. Bonner, Top. Stereochem. 18, 1 (1988); S. F. Mason, Chem. Soc. Rev. 17, 347 (1988); M. Gardner, in The Ambidextrous Universe, C. Scribner, Ed. (Penguin, Harmondsworth, UK, 1982); R. A. Hegstrom and D. R. Kondepudi, Sci. Am. 262, 108 (January 1990); S. F. Mason, Molecular Optical Activity and the Chiral Discriminations (Cambridge Univ. Press, Cambridge, 1982); A. Salam, J. Mol. Evol. 33, 105 (1991); L. D. Barron, New Developments in Molecular Chirality (Kluwer, Dordrecht, Netherlands, 1991); D. K. Kondepudi and G. W. Nelson, Nature 314, 438 (1985); B. S. Green, M. Lahav, D. Rabinovitch, Acc. Chem. Res. 12, 191 (1979)].
9. Discriminative interactions of CPL with racemic materials have been proposed in the context of the origin of chirality [S. L. Milla and L. E. Orgel, The Origin of Life on the Earth (Prentice-Hall. Englewood Cliffs, NJ, 1974); W. A. Bonner, Top. Stereochem. 18, 1 (1988); S. F. Mason, Chem. Soc. Rev. 17, 347 (1988); M. Gardner, in The Ambidextrous Universe, C. Scribner, Ed. (Penguin, Harmondsworth, UK, 1982); R. A. Hegstrom and D. R. Kondepudi, Sci. Am. 262, 108 (January 1990); S. F. Mason, Molecular Optical Activity and the Chiral Discriminations (Cambridge Univ. Press, Cambridge, 1982); A. Salam, J. Mol. Evol. 33, 105 (1991); L. D. Barron, New Developments in Molecular Chirality (Kluwer, Dordrecht, Netherlands, 1991); D. K. Kondepudi and G. W. Nelson, Nature 314, 438 (1985); B. S. Green, M. Lahav, D. Rabinovitch, Acc. Chem. Res. 12, 191 (1979)].
10. Discriminative interactions of CPL with racemic materials have been proposed in the context of the origin of chirality [S. L. Milla and L. E. Orgel, The Origin of Life on the Earth (Prentice-Hall. Englewood Cliffs, NJ, 1974); W. A. Bonner, Top. Stereochem. 18, 1 (1988); S. F. Mason, Chem. Soc. Rev. 17, 347 (1988); M. Gardner, in The Ambidextrous Universe, C. Scribner, Ed. (Penguin, Harmondsworth, UK, 1982); R. A. Hegstrom and D. R. Kondepudi, Sci. Am. 262, 108 (January 1990); S. F. Mason, Molecular Optical Activity and the Chiral Discriminations (Cambridge Univ. Press, Cambridge, 1982); A. Salam, J. Mol. Evol. 33, 105 (1991); L. D. Barron, New Developments in Molecular Chirality (Kluwer, Dordrecht, Netherlands, 1991); D. K. Kondepudi and G. W. Nelson, Nature 314, 438 (1985); B. S. Green, M. Lahav, D. Rabinovitch, Acc. Chem. Res. 12, 191 (1979)].
11. Discriminative interactions of CPL with racemic materials have been proposed in the context of the origin of chirality [S. L. Milla and L. E. Orgel, The Origin of Life on the Earth (Prentice-Hall. Englewood Cliffs, NJ, 1974); W. A. Bonner, Top. Stereochem. 18, 1 (1988); S. F. Mason, Chem. Soc. Rev. 17, 347 (1988); M. Gardner, in The Ambidextrous Universe, C. Scribner, Ed. (Penguin, Harmondsworth, UK, 1982); R. A. Hegstrom and D. R. Kondepudi, Sci. Am. 262, 108 (January 1990); S. F. Mason, Molecular Optical Activity and the Chiral Discriminations (Cambridge Univ. Press, Cambridge, 1982); A. Salam, J. Mol. Evol. 33, 105 (1991); L. D. Barron, New Developments in Molecular Chirality (Kluwer, Dordrecht, Netherlands, 1991); D. K. Kondepudi and G. W. Nelson, Nature 314, 438 (1985); B. S. Green, M. Lahav, D. Rabinovitch, Acc. Chem. Res. 12, 191 (1979)].
12. Discriminative interactions of CPL with racemic materials have been proposed in the context of the origin of chirality [S. L. Milla and L. E. Orgel, The Origin of Life on the Earth (Prentice-Hall. Englewood Cliffs, NJ, 1974); W. A. Bonner, Top. Stereochem. 18, 1 (1988); S. F. Mason, Chem. Soc. Rev. 17, 347 (1988); M. Gardner, in The Ambidextrous Universe, C. Scribner, Ed. (Penguin, Harmondsworth, UK, 1982); R. A. Hegstrom and D. R. Kondepudi, Sci. Am. 262, 108 (January 1990); S. F. Mason, Molecular Optical Activity and the Chiral Discriminations (Cambridge Univ. Press, Cambridge, 1982); A. Salam, J. Mol. Evol. 33, 105 (1991); L. D. Barron, New Developments in Molecular Chirality (Kluwer, Dordrecht, Netherlands, 1991); D. K. Kondepudi and G. W. Nelson, Nature 314, 438 (1985); B. S. Green, M. Lahav, D. Rabinovitch, Acc. Chem. Res. 12, 191 (1979)].
13. Discriminative interactions of CPL with racemic materials have been proposed in the context of the origin of chirality [S. L. Milla and L. E. Orgel, The Origin of Life on the Earth (Prentice-Hall. Englewood Cliffs, NJ, 1974); W. A. Bonner, Top. Stereochem. 18, 1 (1988); S. F. Mason, Chem. Soc. Rev. 17, 347 (1988); M. Gardner, in The Ambidextrous Universe, C. Scribner, Ed. (Penguin, Harmondsworth, UK, 1982); R. A. Hegstrom and D. R. Kondepudi, Sci. Am. 262, 108 (January 1990); S. F. Mason, Molecular Optical Activity and the Chiral Discriminations (Cambridge Univ. Press, Cambridge, 1982); A. Salam, J. Mol. Evol. 33, 105 (1991); L. D. Barron, New Developments in Molecular Chirality (Kluwer, Dordrecht, Netherlands, 1991); D. K. Kondepudi and G. W. Nelson, Nature 314, 438 (1985); B. S. Green, M. Lahav, D. Rabinovitch, Acc. Chem. Res. 12, 191 (1979)].
14. Discriminative interactions of CPL with racemic materials have been proposed in the context of the origin of chirality [S. L. Milla and L. E. Orgel, The Origin of Life on the Earth (Prentice-Hall. Englewood Cliffs, NJ, 1974); W. A. Bonner, Top. Stereochem. 18, 1 (1988); S. F. Mason, Chem. Soc. Rev. 17, 347 (1988); M. Gardner, in The Ambidextrous Universe, C. Scribner, Ed. (Penguin, Harmondsworth, UK, 1982); R. A. Hegstrom and D. R. Kondepudi, Sci. Am. 262, 108 (January 1990); S. F. Mason, Molecular Optical Activity and the Chiral Discriminations (Cambridge Univ. Press, Cambridge, 1982); A. Salam, J. Mol. Evol. 33, 105 (1991); L. D. Barron, New Developments in Molecular Chirality (Kluwer, Dordrecht, Netherlands, 1991); D. K. Kondepudi and G. W. Nelson, Nature 314, 438 (1985); B. S. Green, M. Lahav, D. Rabinovitch, Acc. Chem. Res. 12, 191 (1979)].
15. Discriminative interactions of CPL with racemic materials have been proposed in the context of the origin of chirality [S. L. Milla and L. E. Orgel, The Origin of Life on the Earth (Prentice-Hall. Englewood Cliffs, NJ, 1974); W. A. Bonner, Top. Stereochem. 18, 1 (1988); S. F. Mason, Chem. Soc. Rev. 17, 347 (1988); M. Gardner, in The Ambidextrous Universe, C. Scribner, Ed. (Penguin, Harmondsworth, UK, 1982); R. A. Hegstrom and D. R. Kondepudi, Sci. Am. 262, 108 (January 1990); S. F. Mason, Molecular Optical Activity and the Chiral Discriminations (Cambridge Univ. Press, Cambridge, 1982); A. Salam, J. Mol. Evol. 33, 105 (1991); L. D. Barron, New Developments in Molecular Chirality (Kluwer, Dordrecht, Netherlands, 1991); D. K. Kondepudi and G. W. Nelson, Nature 314, 438 (1985); B. S. Green, M. Lahav, D. Rabinovitch, Acc. Chem. Res. 12, 191 (1979)].
16. Discriminative interactions of CPL with racemic materials have been proposed in the context of the origin of chirality [S. L. Milla and L. E. Orgel, The Origin of Life on the Earth (Prentice-Hall. Englewood Cliffs, NJ, 1974); W. A. Bonner, Top. Stereochem. 18, 1 (1988); S. F. Mason, Chem. Soc. Rev. 17, 347 (1988); M. Gardner, in The Ambidextrous Universe, C. Scribner, Ed. (Penguin, Harmondsworth, UK, 1982); R. A. Hegstrom and D. R. Kondepudi, Sci. Am. 262, 108 (January 1990); S. F. Mason, Molecular Optical Activity and the Chiral Discriminations (Cambridge Univ. Press, Cambridge, 1982); A. Salam, J. Mol. Evol. 33, 105 (1991); L. D. Barron, New Developments in Molecular Chirality (Kluwer, Dordrecht, Netherlands, 1991); D. K. Kondepudi and G. W. Nelson, Nature 314, 438 (1985); B. S. Green, M. Lahav, D. Rabinovitch, Acc. Chem. Res. 12, 191 (1979)].
17. Discriminative interactions of CPL with racemic materials have been proposed in the context of the origin of chirality [S. L. Milla and L. E. Orgel, The Origin of Life on the Earth (Prentice-Hall. Englewood Cliffs, NJ, 1974); W. A. Bonner, Top. Stereochem. 18, 1 (1988); S. F. Mason, Chem. Soc. Rev. 17, 347 (1988); M. Gardner, in The Ambidextrous Universe, C. Scribner, Ed. (Penguin, Harmondsworth, UK, 1982); R. A. Hegstrom and D. R. Kondepudi, Sci. Am. 262, 108 (January 1990); S. F. Mason, Molecular Optical Activity and the Chiral Discriminations (Cambridge Univ. Press, Cambridge, 1982); A. Salam, J. Mol. Evol. 33, 105 (1991); L. D. Barron, New Developments in Molecular Chirality (Kluwer, Dordrecht, Netherlands, 1991); D. K. Kondepudi and G. W. Nelson, Nature 314, 438 (1985); B. S. Green, M. Lahav, D. Rabinovitch, Acc. Chem. Res. 12, 191 (1979)].
18. Photodestruction and photoresolution with CPL has been achieved [K. L. Stevenson and J. K. Verdieck, J. Am. Chem. Soc. 90, 2974 (1968); A. Moradpour, J. F. Nicoud, G. Balavoine, H. Kagan, G. Tsoucaris, ibid. 93, 2353 (1971); Y. Zhang and G. B. Schuster, J. Org. Chem. 60, 7192 (1995)].
19. Photodestruction and photoresolution with CPL has been achieved [K. L. Stevenson and J. K. Verdieck, J. Am. Chem. Soc. 90, 2974 (1968); A. Moradpour, J. F. Nicoud, G. Balavoine, H. Kagan, G. Tsoucaris, ibid. 93, 2353 (1971); Y. Zhang and G. B. Schuster, J. Org. Chem. 60, 7192 (1995)].
20. Photodestruction and photoresolution with CPL has been achieved [K. L. Stevenson and J. K. Verdieck, J. Am. Chem. Soc. 90, 2974 (1968); A. Moradpour, J. F. Nicoud, G. Balavoine, H. Kagan, G. Tsoucaris, ibid. 93, 2353 (1971); Y. Zhang and G. B. Schuster, J. Org. Chem. 60, 7192 (1995)].
21. D. Kreysig and J. Stumpe, in Selected Topics in Liquid Crystal Research, H. D. Koswig, Ed. (Verlag Chemie, Berlin, 1990).
22. H. Rau, Chem. Rev. 83, 535 (1983).
23. Small amounts of an optically active guest molecule added to a nematic host can induce a cholesteric phase, and the helical organization (pitch) in the mesoscopic system is sensitive to modifications in the chiral guest molecule [G. Solladié and R. G. Zimmermann, Angew. Chem. Int. Ed. Engl. 23, 348 (1984)].
24. Recently, photochemical switching between LC phases through use of diastereomeric photoresponsive guest molecules was shown [B. L. Feringa, N. P. M. Huck, H. A. van Doren, J. Am. Chem. Soc. 117, 9929 (1995)].
25. J. Jacques, A. Collet, S. Wilen, Enantiomers, Racemates and Resolutions ( Wiley, New York, 1981).
26. We thank R. M. Kellogg, H. A. van Doren, and J. van Esch for usefull comments.