Structure and morphology of helicene fibers

Journal of the American Chemical Society

Volumn 120, Issue 2, 1998, Pages 264-268

  Lovinger, Andrew J ^a   Nuckolls, Colin ^a   Katz, Thomas J ^a  

^a LUCENT TECHNOLOGIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HELICENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; ELECTRON DIFFRACTION; FIBER; LIQUID; LIQUID CRYSTAL; MICROSCOPY; MORPHOLOGY; NONHUMAN; TRANSMISSION ELECTRON MICROSCOPY; X RAY DIFFRACTION;

EID: 0032554069     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja973366t     Document Type: Article

References (34)

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5. Example of aromatic molecules that gel organic solvents: (a) Lin, Y.; Kachar, B.; Weiss, R. G. J. Am. Chem. Soc. 1989, 111, 5542. (b) Snijder, C. S.; de Jong, J. C.; van Bolhuis, F.; Feringa, B. L. Chem. Eur. J. 1995, 1, 594. (c) van Esch, J.; Kellogg, R. M.; Feringa, B. L. Tetrahedron Lett. 1997, 38, 281. (d) van Nostrum, C. F.; Picken, S. J.; Schouten, A.-J.; Nolte, R. J. M. J. Am. Chem. Soc. 1995, 117, 9957. (e) Brotin, T.; Utermöhlen, R.; Fages, F.; Bouas-Laurent, H.; Desvergne, J.-P. J. Chem. Soc., Chem. Commun. 1991, 416.
6. Example of aromatic molecules that gel organic solvents: (a) Lin, Y.; Kachar, B.; Weiss, R. G. J. Am. Chem. Soc. 1989, 111, 5542. (b) Snijder, C. S.; de Jong, J. C.; van Bolhuis, F.; Feringa, B. L. Chem. Eur. J. 1995, 1, 594. (c) van Esch, J.; Kellogg, R. M.; Feringa, B. L. Tetrahedron Lett. 1997, 38, 281. (d) van Nostrum, C. F.; Picken, S. J.; Schouten, A.-J.; Nolte, R. J. M. J. Am. Chem. Soc. 1995, 117, 9957. (e) Brotin, T.; Utermöhlen, R.; Fages, F.; Bouas-Laurent, H.; Desvergne, J.-P. J. Chem. Soc., Chem. Commun. 1991, 416.
7. Example of aromatic molecules that gel organic solvents: (a) Lin, Y.; Kachar, B.; Weiss, R. G. J. Am. Chem. Soc. 1989, 111, 5542. (b) Snijder, C. S.; de Jong, J. C.; van Bolhuis, F.; Feringa, B. L. Chem. Eur. J. 1995, 1, 594. (c) van Esch, J.; Kellogg, R. M.; Feringa, B. L. Tetrahedron Lett. 1997, 38, 281. (d) van Nostrum, C. F.; Picken, S. J.; Schouten, A.-J.; Nolte, R. J. M. J. Am. Chem. Soc. 1995, 117, 9957. (e) Brotin, T.; Utermöhlen, R.; Fages, F.; Bouas-Laurent, H.; Desvergne, J.-P. J. Chem. Soc., Chem. Commun. 1991, 416.
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14. 1
15. Unpublished experiments by Colin Nuckolls show that the shifts and enhancements extend to solutions as dilute as 0.001 M.
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25. The 1.36-nm peak would then be the (210) reflection from the hexagonal lattice of Figure 1.
26. Heiney, P. A.; Fontes, E.; de Jeu, W. H.; Riera, A.; Carroll, P.; Smith, A. B., III J. Phys. France 1989, 50, 461.
27. In discotic liquid crystals the distances are between 0.33 and 0.56 nm (refs 5d, 5e, 8a-g, 8i, and 10). In crystals the distances are 0.34 nm for benzoperylene [(a) Cotrait, M. C. R. Hebd. Sean. Acad. Sci. Paris, Ser. C 1977, 298, 547], 0.34 nm for coronene [(b) Coucet, J.; Levelut, A. M.; Lambert, M. Acta Crystallogr. 1979, B35, 1102], and 0.35 nm for naphthoquinone [(c) Gaulter, P. J.; Christian, H. Acta Crystallogr. 1965, 18, 179].
28. In discotic liquid crystals the distances are between 0.33 and 0.56 nm (refs 5d, 5e, 8a-g, 8i, and 10). In crystals the distances are 0.34 nm for benzoperylene [(a) Cotrait, M. C. R. Hebd. Sean. Acad. Sci. Paris, Ser. C 1977, 298, 547], 0.34 nm for coronene [(b) Coucet, J.; Levelut, A. M.; Lambert, M. Acta Crystallogr. 1979, B35, 1102], and 0.35 nm for naphthoquinone [(c) Gaulter, P. J.; Christian, H. Acta Crystallogr. 1965, 18, 179].
29. In discotic liquid crystals the distances are between 0.33 and 0.56 nm (refs 5d, 5e, 8a-g, 8i, and 10). In crystals the distances are 0.34 nm for benzoperylene [(a) Cotrait, M. C. R. Hebd. Sean. Acad. Sci. Paris, Ser. C 1977, 298, 547], 0.34 nm for coronene [(b) Coucet, J.; Levelut, A. M.; Lambert, M. Acta Crystallogr. 1979, B35, 1102], and 0.35 nm for naphthoquinone [(c) Gaulter, P. J.; Christian, H. Acta Crystallogr. 1965, 18, 179].
30. The X-ray diffraction was recorded in a vacuum with use of Nifiltered Cu Ka radiation. The intense peak and the second- and third-order peaks for the 3.6-nm spacing, as well as broad diffuse outer rings in the region 0.3-0.5 nm, were seen. There was no orientational preference, indicating that fibers prepared in this way are organized in the same way as those prepared by heating and cooling, but are comprised of random aggregates.
31. Grubb, D. T. J. Mater. Sci. 1974, 9, 1715.
32. In polyethylene 0.249, 0.374, and 0.414 nm, respectively: Dorset, D. Macromolecules 1991, 24, 1175.
33. Bunn, C. W. Trans. Faraday Soc. 1939, 482.
34. Spots separated by 60°, perpendicular to fibers and at low angles, expected for hexagonal order, have been observed in liquid crystalline fibers of triphenylenes [Chiang, L. Y.; Safinya, C. R.; Clark, N. A.; Liang, K. S.; Bloch, A. N. J. Chem. Soc., Chem. Commun. 1985, 695] and truxenes (ref 8h).