Syntheses of functionalized and aggregating helical conjugated helical conjugated molecules

Angewandte Chemie - International Edition

Volumn 39, Issue 11, 2000, Pages 1921-1923

  Katz, Thomas J ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

Aggregation; Helical structures; Supramolecular chemistry; Synthesis design; Synthetic methods

Indexed keywords

1,10 PHENANTHROLINE; 2,2' BIPYRIDINE; ACETONITRILE; ACETYLENE; AROMATIC COMPOUND;

ARTICLE; CHEMICAL STRUCTURE; CONFORMATION; SYNTHESIS;

EID: 0034595710     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20000602)39:11<1921::AID-ANIE1921>3.0.CO;2-F     Document Type: Article

References (31)

1. W. H. Laarhoven, W. J. C. Prinsen, Top. Curr. Chem. 1984, 125, 63.
2. S. D. Dreher, D. Weix, T. J. Katz, J. Org. Chem. 1999, 64, 3671, and references therein.
3. a) C. Nuckolls, T. J. Katz, G. Katz, P. J. Collings, L. Castellanos, J. Am. Chem. Soc. 1999, 121, 79, and references therein;
4. b) T. Thongpanchang, K. Paruch, T. J. Katz, A. L. Rheingold, K.-C. Lam, L. Liable-Sands, J. Org. Chem. 2000, 65, 1850, and references therein.
5. C. Nuckolls, T. J. Katz, J. Am. Chem. Soc. 1998, 120, 9541.
6. Moreover, since this response arises in essence entirely from the material's chirality, a structure comprised of alternating layers of the impoled enantiomers, in which each layer is one coherence length thick, gives rise to second harmonics that are quasi-phase matched (B. Busson, M. Kauranen, C. Nuckolls, T. J. Katz, A. Persoons, Phys. Rev. Lett. 2000, 84, 79, and references therein).
7. a) M. T. Reetz, E. W. Beuttenmüller, R. Goddard, Tetrahedron Lett. 1997, 38, 3211;
8. b) A. Terfort, H. Görls, H. Brunner, Synthesis 1997, 79;
9. c) S. D. Dreher, T. J. Katz, K.-C. Lam, A. L. Rheingold, J. Org. Chem. 2000, 65, 815.
10. I. G. Stará, I. Starý, A. Kollárovič, F. Teplý, Š. Vyskočil, D. Šaman, Tetrahedron Lett. 1999, 40, 1993, and references therein.
11. X. Qiao, D. M. Ho, R. A. Pascal, Jr., Angew. Chem. 1997, 109, 1588; Angew. Chem. Int. Ed. Engl. 1997, 36, 1531.
12. X. Qiao, D. M. Ho, R. A. Pascal, Jr., Angew. Chem. 1997, 109, 1588; Angew. Chem. Int. Ed. Engl. 1997, 36, 1531.
13. B. L. Feringa, N. P. M. Huck, A. M. Schoevaars, Adv. Mater. 1996, 8, 681.
14. a) S. Misumi in Cyclophanes, Vol. II (Eds.: P. M. Keehn, S. M. Rosenfeld), Academic, New York, 1983, p. 573, and references therein;
15. b) J. Harren, A. Sohanski, M. Nieger, C. Yamamoto, Y. Okamoto, F. Vögtle, Tetrahedron: Asymmetry 1998, 9, 1369, and references therein;
16. c) S. Grimme, J. Harren, A. Sohanski, F. Vögtle, Eur. J. Org. Chem. 1998, 1491.
17. a) M. S. Gin, T. Yokozawa, R. B. Prince, J. S. Moore, J. Am. Chem. Soc. 1999, 121, 2643, and references therein;
18. b) M. S. Gin, J. S. Moore, Org. Lett. 2000, 2, 135;
19. c) L. A. Cuccia, J.-M. Lehn, J.-C. Homo, M. Schmutz, Angew. Chem. 2000, 112, 239; Angew. Chem. Int. Ed. 2000, 39, 233, and references therein.
20. L. A. Cuccia, J.-M. Lehn, J.-C. Homo, M. Schmutz, Angew. Chem. 2000, 112, 239; Angew. Chem. Int. Ed. 2000, 39, 233, and references therein.
21. A short review: A. E. Rowan, R. J. M. Nolte, Angew. Chem. 1998, 110, 65; Angew. Chem. Int. Ed. 1998, 37, 63.
22. A short review: A. E. Rowan, R. J. M. Nolte, Angew. Chem. 1998, 110, 65; Angew. Chem. Int. Ed. 1998, 37, 63.
23. Lehn, using a vitalistic vocabulary, attributes the helical conformation of 6 to a "helicity codon" rather than to a directing effect.
24. The precise meaning of these figures is unclear.
25. A. S. Shetty, J. Zhang, J. S. Moore, J. Am. Chem. Soc. 1996, 118, 1019.
26. S. Rozen, S. Dayan, Angew. Chem. 1999, 111, 3682; Angew. Chem. Int. Ed. 1999, 38, 3471.
27. S. Rozen, S. Dayan, Angew. Chem. 1999, 111, 3682; Angew. Chem. Int. Ed. 1999, 38, 3471.
28. R. Antkowiak, W. Z. Antkowiak, Tetrahedron Lett. 1997, 38, 1857; R. Antkowiak, W. Z. Antkowiak, Heterocyctes 1998, 47, 893.
29. R. Antkowiak, W. Z. Antkowiak, Tetrahedron Lett. 1997, 38, 1857; R. Antkowiak, W. Z. Antkowiak, Heterocyctes 1998, 47, 893.
30. R. N. Armstrong, H. L. Ammon, J. N. Darnow, J. Am. Chem. Soc. 1987, 109, 2077.
31. H. A. Staab, M. Diehm, C. Krieger, Tetrahedron Lett. 1994, 35, 8357.