A Chiroptical Molecular Switch with Distinct Chiral and Photochromic Entities and Its Application in Optical Switching of a Cholesteric Liquid Crystal

Chemistry - A European Journal

Volumn 10, Issue 1, 2004, Pages 61-70

  Van Delden, Richard A ^a   Mecca, Tommaso ^b,c   Rosini, Carlo ^b   Feringa, Ben L ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

^b UNIVERSITY OF BASILICATA   (Italy)

^c CNR   (Italy)

Author keywords

Biaryls; Chirality; Isomerization; Liquid crystals molecular switches; Photochromism

Indexed keywords

CONFORMATIONS; ETHERS; MOLECULAR STRUCTURE; OPTICAL SWITCHES;

MOLECULAR SWITCHES;

LIQUID CRYSTALS;

AZOBENZENE DERIVATIVE; BRIDGED COMPOUND; CARBENOID; CHOLESTEROL; NAPHTHYL GROUP;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; CHIRALITY; CIRCULAR DICHROISM; CIS TRANS ISOMERISM; CONFORMATIONAL TRANSITION; ISOMERIZATION; LIQUID CRYSTAL; STEREOSPECIFICITY; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 0347719289     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200305276     Document Type: Article

References (70)

1. a) Sci. Amer. Special Issue: Nanotech: The Science of Small Gets Down to Business, September 2001;
2. b) R. P. Feynman in Miniaturization (Ed.: H. D. Gilbert), New York, 1971;
3. c) K. E. Drexler, Nano-systems: Molecular Machinery, Manufacturing and Computation, Wiley, New York, 1992;
4. d) R. D. Astumian, Sci. Amer. 2001, 285, 56-64.
5. Molecular Switches (Ed.: B. L. Feringa), Wiley-VCH, Weinheim, 2001.
6. Special Issue: Photochromism: Memories and Switches, Chem. Rev. 2000 (Guest Ed.: M. Irie), 100, 1683-1890.
7. See for example: a) O. Pieroni, A. Fissi, G. Popova, Prog. Polym. Sci. 1998, 23, 81-123;
8. b) F. Ciardelli, O. Pieroni, A. Fissi, C. Carlini, A. Altomare, Br. Polym. J. 1989, 21, 97-106;
9. c) M. Irie, Adv. Polym. Sci. 1990, 94, 27-67;
10. d) Applied Photochromic Polymer Systems (Ed.: C. B. McArdle), Blackie, Glasgow (UK), 1992;
11. e) F. Ciardelli, O. Pieroni, A. Fissi, J. L. Houben, Biopolymers 1984, 23, 1423-1437;
12. f) O. Pieroni, F. Ciardelli, Trends Polym. Sci. 1995, 3, 282-287;
13. g) T. Kinoshita, Prog. Polym. Sci. 1995, 20, 527-583;
14. h) I. Willner, Acc. Chem. Res. 1997, 30, 347-356.
15. F. Ciardelli, O. Pieroni in Chiroptical Molecular Switches (Ed.: B. L. Feringa), Wiley-VCH, Weinheim, 2001, Chapter 13, pp. 399-441.
16. M. Irie, S. Kobatake, M. Horichi, Science 2001, 291, 1769-1772.
17. T. Ikeda, A. Kanazawa in Chiroptical Molecular Switches (Ed.: B. L. Feringa), Wiley-VCH, Weinheim, 2001, Chapter 12, pp. 363-397.
18. a) B. L. Feringa, R. A. van Delden, N. Koumura, E. M. Geertsema, Chem. Rev. 2000, 100, 1789-1816;
19. b) B. L. Feringa, R. A. van Delden, M. K. J. ter Wiel in Molecular Switches (Ed.: B. L. Feringa), Wiley-VCH, Weinheim, 2001, Chapter 5, pp. 123-163.
20. B. L. Feringa, N. P. M. Huck, H. A. van Doren, J. Am. Chem. Soc. 1995, 117, 9929-9930.
21. See for example: a) T. Yamaguchi, K. Uchida, M. Irie, J. Am. Chem. Soc. 1997, 119, 6066-6071;
22. b) T. Yamaguchi, Y. Tanaka, H. Nakazumi, K. Uchida, T. Yamada, M. Irie, Enantiomer 2001, 6, 309-311;
23. c) Y. Yokoyama, S. Uchida, Y. Shimizu, Y. Yokoyama, Mol. Cryst. Liq. Cryst. 1997, 297, 85-91;
24. d) Y. Yokoyama, S. Uchida, Y. Yokoyama, Y. Sugawara, Y. Kurita, J. Am. Chem. Soc. 1996, 118, 3100-3107;
25. e) L. Eggers, V. Buß, Angew. Chem. 1997, 109, 885-887; Angew. Chem. Int. Ed. Engl. 1997, 36, 881-883;
26. L. Eggers, V. Buß, Angew. Chem. 1997, 109, 885-887; Angew. Chem. Int. Ed. Engl. 1997, 36, 881-883;
27. f) A. Miyashita, A. Iwamoto, T. Kuwayama, H. Shitara, Y. Aoki, M. Hirano, H. Nohira, Chem. Lett. 1997, 965-966;
28. g) T. Ikeda, T. Sasaki, K. Ichimura, Nature 1993, 361. 428;
29. h) T. Kusumoto, K. Sato, K. Ogino, T. Hiyama, S. Takehara, M. Osawa, K. Nakamura, Liq. Cryst. 1993, 14, 727-732;
30. i) M. Negishi, O. Tutsumi, T. Ikeda, T. Hiyama, J. Kawamura, M. Aizawa, S. Takehara, Chem. Lett. 1996, 319-320;
31. j) M. Negishi, K. Kanie, T. Ikeda, T. Hiyama, Chem. Lett. 1996, 583-584;
32. k) T. Ikeda, O. Tsutsum, Science 1995, 268, 1873-1875.
33. See for example: a) S. Z. Janicki, G. B. Schuster, J. Am. Chem. Soc. 1995, 117, 8524-8527;
34. b) Y. Yokoyama, T. Sagisaka, Chem. Lett. 1997, 687-688;
35. c) C. Denekamp, B. L. Feringa, Adv. Mater. 1998, 10, 1080-1082;
36. d) C. Ruslim, K. Ichimura, Adv. Mater. 2001, 13, 37-40;
37. e) G. Heppke, H. Marshall, P. Nurnberg, F. Oestreicher, G. Sherowsky, Chem. Ber. 1981, 114, 2501-2518.
38. S. Pieraccini, S. Masiero, G. P. Spada, G. Gottarelli, Chem. Commun. 2003, 598-599.
39. a) C. Rosini, L. Franzini, A. Raffaelli, P. Salvadori, Synthesis 1992, 503-517;
40. b) L. Pu, H.-B. Yu, Chem. Rev. 2001, 101, 757-824;
41. c) B. L. Feringa, Acc. Chem. Res. 2000, 33, 346-353.
42. a) G. Gottarelli, M. Hibert, B. Samori, G. Solladié, G. P. Spada, R. Zimmermann, J. Am. Chem. Soc. 1983, 105, 7318-7321;
43. b) G. Gottarelli, G. P. Spada, R. Bartsch, G. Solladié, R. Zimmermann, J. Org. Chem. 1986, 51, 589-592;
44. c) G. Solladié, G. Gottarelli, Tetrahedron 1987, 43, 1425-1437;
45. d) P. V. Shibaev, K. Schaumberg, T. Bjornholm, Mol. Cryst. Liq. Cryst. 2000. 338, 181-195;
46. e) G. Gottarelli, G. P. Spada, Mol. Cryst. Liq. Cryst. 1985, 123, 377;
47. f) P. V. Shibaev, R. Vinokur, H.-J. Deussen, T. Bjørnholm, K. Schaumberg, SPIE 1997, 3319, 185.
48. a) A. Ferrarini, G. J. Moro, P. L. Nordio, Liq. Cryst. 1995, 189, 397-399;
49. b) A. Ferrarini, G. J. Moro, P. L. Nordio. Phys. Rev. E 1996, 53, 681-688.
50. G. D. Y. Sogah, D. J. Cram, J. Am. Chem. Soc. 1979, 101, 3035-3042.
51. H. J. Deussen, E. Hendrickx. C. Boutton, D. Krog, K. Clays, K. Bechgaard, A. Persoons, T. Bjornholm, J. Am. Chem. Soc. 1996, 118, 6841-6852.
52. a) S. F. Mason, R. H. Seal, D. R. Roberts, Tetrahedron 1974, 30, 1671-1682;
53. b) C. Rosini, I. Rosati, G. P. Spada, Chirality 1995, 7, 353-358;
54. c) C. Rosini, S. Superchi, H. W. I. Peerlings, E. W. Meijer, Eur. J. Org. Chem. 2000, 61-71.
55. H. Suzuki, Electronic Absorption Spectra and Geometry of Organic Molecules, Academic Press, New York, 1967, p. 503.
56. J. J. G. S. van Es, H. A. M. Biemans, E. W. Meijer, Tetrahedron: Asymmetry 1997, 8, 1825-1831.
57. H. Rau in Photochromism, molecules and systems (Eds.: H. Dürr, H. Bouas-Laurent), Elsevier, Amsterdam, 1990, Chapter 4, pp. 165-192.
58. a) Z. Sekkat, W. Knoll J. Opt. Soc Am. B 1995, 12, 1855-1867;
59. b) O. Watanabe, M. Tsuchimori, A. Okada, J. Mater. Chem. 1996, 6, 1487-1492;
60. c) C. Egami, Y. Suzuki, O. Sugihara, N. Okamoto, H. Fujimura, K. Nakagawa, H. Fujiwara, Appl. Phys. B 1997, 64, 471-478;
61. d) C. Wang, H. Fei, Y. Yang, Z. Wei, Y. Qui, Y. Chen, Opt. Commun. 1999, 159, 58-62.
62. a) G. Heppke, F. Oesterreicher, Z. Naturforsch. A 1977, 32, 899-901;
63. b) G. Gottarelli, B. Samori, C. Stremmenos, G. Torre, Tetrahedron 1981, 37, 395-399.
64. G. Solladié, R. G. Zimmermann, Angew. Chem. 1984, 96, 335-349; Angew. Chem. Int. Ed. Engl. 1984, 23, 348-362.
65. G. Solladié, R. G. Zimmermann, Angew. Chem. 1984, 96, 335-349; Angew. Chem. Int. Ed. Engl. 1984, 23, 348-362.
66. Helical twisting power: β = (pcr)-1, where p is the pitch (μm), c is the concentration (g of dopant per gram of LC solution) and r is the enantiomeric purity of the dopant.
67. Light of 402 nm proved to be a slightly more selective wavelength for switching in an LC phase, in solution the selectivity observed upon irradiation with this wavelength is slightly (about 2%) less than the ideal 405 nm.
68. A. di Matteo, S. M. Todd, G. Gottarelli, G. Solladié, V. E. Williams, R. P. Lemieux, A. Ferrarini and G. P. Spada, J. Am. Chem. Soc. 2001, 123, 7842-7851.
69. a) F. Grandjean, C. R. Acad. Sci. 1921, 172, 71; b) R. Cano, Bull. Soc. Fr. Mineral 1968, 91, 20.
70. a) F. Grandjean, C. R. Acad. Sci. 1921, 172, 71; b) R. Cano, Bull. Soc. Fr. Mineral 1968, 91, 20.