Helical bias in solvophobically folded oligo(phenylene ethynylene)s [24]

Journal of the American Chemical Society

Volumn 121, Issue 11, 1999, Pages 2643-2644

  Gin, Mary S ^a   Yokozawa, Tsutomu ^a,b   Prince, Ryan B ^a   Moore, Jeffrey S ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

^b KANAGAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

NAPHTHOL DERIVATIVE; OLIGOMER; SOLVENT;

CHEMICAL STRUCTURE; CHIRALITY; CIRCULAR DICHROISM; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LETTER; MASS SPECTROMETRY; OLIGOMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0033599526     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja984017h     Document Type: Letter

References (24)

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9. For examples in which chiral monomers result in the formation of biased helical polymers, see: (a) Schlitzer, D. S.; Novak, B. M. J. Am. Chem. Soc. 1998, 120, 2196. (b) Green, M. M.; Peterson, N. C.; Sato, T.; Teramoto, A.; Cook, R.; Lifson, S. Science 1995, 268, 1860. (c) Wittung, P.; Eriksson, M.; Lyng, R.; Nielsen, P. E.; Norden, B. J. Am. Chem. Soc. 1995, 117, 10167. (d) References la-c and f. For examples in which chiral additives impart a bias on helical polymers, see: (e) ref 2a and Yashima, E.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1997, 119, 6345. For an example in which a chiral initiator resulted in the formation of a biased helical oligomer, see: (f) Ito, Y.; Miyake, T.; Hatano, S.; Shima, R.; Ohara, T.; Suginome, M. J. Am. Chem. Soc. 1998, 120, 11880. For a leading reference on helicates, see: (g) Piguet, C.; Bernardinelli, G.; Hopfgartner, G. Chem. Rev. 1997, 97, 2005. For an example of helical aggregates formed from an optically active helicene, see: (h) Nuckolls, C.; Katz, T. J., Verbiest, T.; Van Elshocht, S.; Kuball, H.-G.; Kiesewalter, S.; Lovinger, A. J.; Persoons, A. J. Am. Chem. Soc. 1998, 120, 8656. For a review on the use of binaphthyls in macromolecular systems, see: (i) Pu, L. Chem. Rev. 1998, 98, 2405.
10. For examples in which chiral monomers result in the formation of biased helical polymers, see: (a) Schlitzer, D. S.; Novak, B. M. J. Am. Chem. Soc. 1998, 120, 2196. (b) Green, M. M.; Peterson, N. C.; Sato, T.; Teramoto, A.; Cook, R.; Lifson, S. Science 1995, 268, 1860. (c) Wittung, P.; Eriksson, M.; Lyng, R.; Nielsen, P. E.; Norden, B. J. Am. Chem. Soc. 1995, 117, 10167. (d) References la-c and f. For examples in which chiral additives impart a bias on helical polymers, see: (e) ref 2a and Yashima, E.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1997, 119, 6345. For an example in which a chiral initiator resulted in the formation of a biased helical oligomer, see: (f) Ito, Y.; Miyake, T.; Hatano, S.; Shima, R.; Ohara, T.; Suginome, M. J. Am. Chem. Soc. 1998, 120, 11880. For a leading reference on helicates, see: (g) Piguet, C.; Bernardinelli, G.; Hopfgartner, G. Chem. Rev. 1997, 97, 2005. For an example of helical aggregates formed from an optically active helicene, see: (h) Nuckolls, C.; Katz, T. J., Verbiest, T.; Van Elshocht, S.; Kuball, H.-G.; Kiesewalter, S.; Lovinger, A. J.; Persoons, A. J. Am. Chem. Soc. 1998, 120, 8656. For a review on the use of binaphthyls in macromolecular systems, see: (i) Pu, L. Chem. Rev. 1998, 98, 2405.
11. For examples in which chiral monomers result in the formation of biased helical polymers, see: (a) Schlitzer, D. S.; Novak, B. M. J. Am. Chem. Soc. 1998, 120, 2196. (b) Green, M. M.; Peterson, N. C.; Sato, T.; Teramoto, A.; Cook, R.; Lifson, S. Science 1995, 268, 1860. (c) Wittung, P.; Eriksson, M.; Lyng, R.; Nielsen, P. E.; Norden, B. J. Am. Chem. Soc. 1995, 117, 10167. (d) References la-c and f. For examples in which chiral additives impart a bias on helical polymers, see: (e) ref 2a and Yashima, E.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1997, 119, 6345. For an example in which a chiral initiator resulted in the formation of a biased helical oligomer, see: (f) Ito, Y.; Miyake, T.; Hatano, S.; Shima, R.; Ohara, T.; Suginome, M. J. Am. Chem. Soc. 1998, 120, 11880. For a leading reference on helicates, see: (g) Piguet, C.; Bernardinelli, G.; Hopfgartner, G. Chem. Rev. 1997, 97, 2005. For an example of helical aggregates formed from an optically active helicene, see: (h) Nuckolls, C.; Katz, T. J., Verbiest, T.; Van Elshocht, S.; Kuball, H.-G.; Kiesewalter, S.; Lovinger, A. J.; Persoons, A. J. Am. Chem. Soc. 1998, 120, 8656. For a review on the use of binaphthyls in macromolecular systems, see: (i) Pu, L. Chem. Rev. 1998, 98, 2405.
12. For examples in which chiral monomers result in the formation of biased helical polymers, see: (a) Schlitzer, D. S.; Novak, B. M. J. Am. Chem. Soc. 1998, 120, 2196. (b) Green, M. M.; Peterson, N. C.; Sato, T.; Teramoto, A.; Cook, R.; Lifson, S. Science 1995, 268, 1860. (c) Wittung, P.; Eriksson, M.; Lyng, R.; Nielsen, P. E.; Norden, B. J. Am. Chem. Soc. 1995, 117, 10167. (d) References la-c and f. For examples in which chiral additives impart a bias on helical polymers, see: (e) ref 2a and Yashima, E.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1997, 119, 6345. For an example in which a chiral initiator resulted in the formation of a biased helical oligomer, see: (f) Ito, Y.; Miyake, T.; Hatano, S.; Shima, R.; Ohara, T.; Suginome, M. J. Am. Chem. Soc. 1998, 120, 11880. For a leading reference on helicates, see: (g) Piguet, C.; Bernardinelli, G.; Hopfgartner, G. Chem. Rev. 1997, 97, 2005. For an example of helical aggregates formed from an optically active helicene, see: (h) Nuckolls, C.; Katz, T. J., Verbiest, T.; Van Elshocht, S.; Kuball, H.-G.; Kiesewalter, S.; Lovinger, A. J.; Persoons, A. J. Am. Chem. Soc. 1998, 120, 8656. For a review on the use of binaphthyls in macromolecular systems, see: (i) Pu, L. Chem. Rev. 1998, 98, 2405.
13. For examples in which chiral monomers result in the formation of biased helical polymers, see: (a) Schlitzer, D. S.; Novak, B. M. J. Am. Chem. Soc. 1998, 120, 2196. (b) Green, M. M.; Peterson, N. C.; Sato, T.; Teramoto, A.; Cook, R.; Lifson, S. Science 1995, 268, 1860. (c) Wittung, P.; Eriksson, M.; Lyng, R.; Nielsen, P. E.; Norden, B. J. Am. Chem. Soc. 1995, 117, 10167. (d) References la-c and f. For examples in which chiral additives impart a bias on helical polymers, see: (e) ref 2a and Yashima, E.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1997, 119, 6345. For an example in which a chiral initiator resulted in the formation of a biased helical oligomer, see: (f) Ito, Y.; Miyake, T.; Hatano, S.; Shima, R.; Ohara, T.; Suginome, M. J. Am. Chem. Soc. 1998, 120, 11880. For a leading reference on helicates, see: (g) Piguet, C.; Bernardinelli, G.; Hopfgartner, G. Chem. Rev. 1997, 97, 2005. For an example of helical aggregates formed from an optically active helicene, see: (h) Nuckolls, C.; Katz, T. J., Verbiest, T.; Van Elshocht, S.; Kuball, H.-G.; Kiesewalter, S.; Lovinger, A. J.; Persoons, A. J. Am. Chem. Soc. 1998, 120, 8656. For a review on the use of binaphthyls in macromolecular systems, see: (i) Pu, L. Chem. Rev. 1998, 98, 2405.
14. For examples in which chiral monomers result in the formation of biased helical polymers, see: (a) Schlitzer, D. S.; Novak, B. M. J. Am. Chem. Soc. 1998, 120, 2196. (b) Green, M. M.; Peterson, N. C.; Sato, T.; Teramoto, A.; Cook, R.; Lifson, S. Science 1995, 268, 1860. (c) Wittung, P.; Eriksson, M.; Lyng, R.; Nielsen, P. E.; Norden, B. J. Am. Chem. Soc. 1995, 117, 10167. (d) References la-c and f. For examples in which chiral additives impart a bias on helical polymers, see: (e) ref 2a and Yashima, E.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1997, 119, 6345. For an example in which a chiral initiator resulted in the formation of a biased helical oligomer, see: (f) Ito, Y.; Miyake, T.; Hatano, S.; Shima, R.; Ohara, T.; Suginome, M. J. Am. Chem. Soc. 1998, 120, 11880. For a leading reference on helicates, see: (g) Piguet, C.; Bernardinelli, G.; Hopfgartner, G. Chem. Rev. 1997, 97, 2005. For an example of helical aggregates formed from an optically active helicene, see: (h) Nuckolls, C.; Katz, T. J., Verbiest, T.; Van Elshocht, S.; Kuball, H.-G.; Kiesewalter, S.; Lovinger, A. J.; Persoons, A. J. Am. Chem. Soc. 1998, 120, 8656. For a review on the use of binaphthyls in macromolecular systems, see: (i) Pu, L. Chem. Rev. 1998, 98, 2405.
15. For examples in which chiral monomers result in the formation of biased helical polymers, see: (a) Schlitzer, D. S.; Novak, B. M. J. Am. Chem. Soc. 1998, 120, 2196. (b) Green, M. M.; Peterson, N. C.; Sato, T.; Teramoto, A.; Cook, R.; Lifson, S. Science 1995, 268, 1860. (c) Wittung, P.; Eriksson, M.; Lyng, R.; Nielsen, P. E.; Norden, B. J. Am. Chem. Soc. 1995, 117, 10167. (d) References la-c and f. For examples in which chiral additives impart a bias on helical polymers, see: (e) ref 2a and Yashima, E.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1997, 119, 6345. For an example in which a chiral initiator resulted in the formation of a biased helical oligomer, see: (f) Ito, Y.; Miyake, T.; Hatano, S.; Shima, R.; Ohara, T.; Suginome, M. J. Am. Chem. Soc. 1998, 120, 11880. For a leading reference on helicates, see: (g) Piguet, C.; Bernardinelli, G.; Hopfgartner, G. Chem. Rev. 1997, 97, 2005. For an example of helical aggregates formed from an optically active helicene, see: (h) Nuckolls, C.; Katz, T. J., Verbiest, T.; Van Elshocht, S.; Kuball, H.-G.; Kiesewalter, S.; Lovinger, A. J.; Persoons, A. J. Am. Chem. Soc. 1998, 120, 8656. For a review on the use of binaphthyls in macromolecular systems, see: (i) Pu, L. Chem. Rev. 1998, 98, 2405.
16. For examples in which chiral monomers result in the formation of biased helical polymers, see: (a) Schlitzer, D. S.; Novak, B. M. J. Am. Chem. Soc. 1998, 120, 2196. (b) Green, M. M.; Peterson, N. C.; Sato, T.; Teramoto, A.; Cook, R.; Lifson, S. Science 1995, 268, 1860. (c) Wittung, P.; Eriksson, M.; Lyng, R.; Nielsen, P. E.; Norden, B. J. Am. Chem. Soc. 1995, 117, 10167. (d) References la-c and f. For examples in which chiral additives impart a bias on helical polymers, see: (e) ref 2a and Yashima, E.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1997, 119, 6345. For an example in which a chiral initiator resulted in the formation of a biased helical oligomer, see: (f) Ito, Y.; Miyake, T.; Hatano, S.; Shima, R.; Ohara, T.; Suginome, M. J. Am. Chem. Soc. 1998, 120, 11880. For a leading reference on helicates, see: (g) Piguet, C.; Bernardinelli, G.; Hopfgartner, G. Chem. Rev. 1997, 97, 2005. For an example of helical aggregates formed from an optically active helicene, see: (h) Nuckolls, C.; Katz, T. J., Verbiest, T.; Van Elshocht, S.; Kuball, H.-G.; Kiesewalter, S.; Lovinger, A. J.; Persoons, A. J. Am. Chem. Soc. 1998, 120, 8656. For a review on the use of binaphthyls in macromolecular systems, see: (i) Pu, L. Chem. Rev. 1998, 98, 2405.
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19. Although our data supports an intramolecular folding event, others have obtained similar data and attributed the changes to intermolecular aggregation, see: Cornelissen, J.; Peeters, E.; Janssen, R. A.; Meijer, E. W. Acta Polym. 1998, 49, 471.
20. Minimizations were performed using Macromodel 5.5 and the OPLS* GB/SA force field. Monte Carlo searches from several different initial conformations yielded the structure shown in Figure 1 as the global minimum.
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24. Prince, R. B.; Moore, J. S., unpublished results.