Unique Properties of Chromophore-Containing Bilayer Aggregates: Enhanced Chirality and Photochemically Induced Morphological Change

Journal of the American Chemical Society

Volumn 102, Issue 21, 1980, Pages 6642-6644

  Kunitake, T ^a   Nakashima, N ^a   Shimomura, M ^a   Okahata, Y ^a   Kano, K ^a   Ogawa, T ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 3142670321     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00541a081     Document Type: Article

References (27)

1. Contribution No. 569 from the Department of Organic Synthesis.
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7. Kunitake, T.; Okahata, Y. Chem. Lett. 1977, 1337-1340.
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9. Tran, C. D.; Klahn, P. L.; Romero, A.; Fendler, J. H. J. Am. Chem. Soc. 1978, 100, 1622-1623.
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14. This compound was prepared by condensation of didodecyl L-glutamate and p-(4-bromobutoxy)benzoic acid and the subsequent quater-nization with trimethylamine; mp 45-220 °C (the liquid crystalline behavior was observed in this temperature range), [α]20D +7.46° (c 2.00, CHCI3). D-1 and DL-1 were similarly prepared. The purity was confirmed by elemental analysis, thin-layer chromatography, and 1H NMR spectroscopy.
15. Sonication of an aqueous suspension of 1 was carried out by using a Branson ultrasonic cleaner 12 (bath type) for 3-5 min. The aggregate weight was 6 × 109. When L-1 was sonicated with the cell disrupter for 5-10 min, the low-temperature CD spectrum could not be observed even after aging for 10 h at 0 °C.
16. Ralston, A. W.; Eggenbergcr, D. N.; DuBrow, P. L. J. Am. Chem. Soc. 1945, 70, 977-979
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19. Saeva, F. D.; Olin, G. R. J. Am. Chem. Soc. 1977, 99, 4848-4850.
20. Jonansson, L.B.-Å.; Davidson, Å.; Lindblom, G.; Nordén, B.; J. Phys. Chem. 1978, 82, 2604-2609.
21. Special Issue on the Chemistry of Vision, Acc. Chem. Res. 1975, 8, 81-112
22. Recent papers include the following examples, (a) Polymers: Paik, C. S.; Morawetz, H. Macromolecules 1972, 5, 171-177, Eisenbach, C. D. Makromol Chem. 1978, 179, 2489-2506. Ueno, A.; Anzai, J.; Osa, T. J. Polym. Sci., Potym. Lett. Ed. 1979,17, 149-154.
23. Liquid crystals: Pelzl, G. Z. Chem. 1977, 17, 294-295. Leier, C.; Pelzl, G. J. Prakl. Chem. 1979, 321, 197-204.
24. Cyclodextrin; Ueno, A.; Yoshimura, H.; Saka, R.; Osa, T. J. Am. Chem. Soc. 1979, 101, 2779-2780. Ueno, A.; Saka, R.; Osa, T. Chem. Lett. 1979, 841-844, 1007-1010.
25. Crown ethers; Shinkai, S.; Ogawa, T.; Nakaji, T.; Kusano, Y.; Manabe, O. Tetrahedron Lett. 1979, 4569-4572. Shinkai, S.; Ogawa, T.; Kusano, Y.; Manabe, O. Chem. Lett. 1980, 283-286.
26. This amphiphile was prepared by coupling of p-dodecylaniline and phenol, followed by alkylation and quaternization. The final product was identified by elemental analysis, NMR and IR spectroscopies, and thin-laycr chromatography.
27. The amphiphile solution as prepared by sonication (and the subsequent aging in an ice bath for 30 min) was mixed with an equal volume of 2% aqueous uranyl acetate, sonicated for 10-20 s, and applied to carbon-coated Cu grids for electron microscopy (Hitachi Model H-500). The photoisomerization was performed with and without uranyl acetate. The resulting morphologies were the same.