Helical macromolecules are ubiquitous in nature, and almost always adopt a one-handed conformation. Synthetic systems, in contrast, are typically obtained in racemic right- and left-handed mixtures. A helical phenylene oligomer has now been prepared that forms a non-racemic mixture on crystallization, and on oxidation locks one conformation in.
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References
Yashima, E., Maeda, K., Iida, H., Furusho, Y. & Nagai, K. Chem. Rev. 109, 6102–6211 (2009).
Green, M. M. et al. Science 268, 1860–1866 (1995).
Ohta, E. et al. Nature Chem. 10.1038/nchem.900 3, 68–73 (2011).
Berresheim, A. J., Müller, M. & Müllen, K. Chem. Rev. 99, 1747–1786 (1999).
Blake, A. J., Cooke, P. A., Doyle, K. J., Gair, S. & Simpkins, N. S. Tetrahedron Lett. 39, 9093–9096 (1998).
Ormsby, J. L., Black, T. D., Hilton, C. L., Bharat & King, B. T. Tetrahedron 64, 11370–11378 (2008).
Avalos, M., Babiano, R., Cintas, P., Jiménez, L. & Palacios, J. C. Tetrahedron Asymm. 11, 2845–2874 (2000).
Kondepudi, D. K., Kaufman, R. J. & Singh, N. Science 250, 975–976 (1990).
Hida, N. et al. Angew. Chem. Int. Ed. 42, 4349–4352 (2003).
He, J. et al. J. Am. Chem. Soc. 132, 13848–13857 (2010).
Prince, R. B., Barnes, S. A. & Moore, J. S. J. Am. Chem. Soc. 112, 2758–2762 (2000).
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Yashima, E. Breaking free of chiral symmetry. Nature Chem 3, 12–14 (2011). https://doi.org/10.1038/nchem.939
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DOI: https://doi.org/10.1038/nchem.939
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