Angewandte Chemie - International Edition
Angewandte Chemie - International Edition
4 years ago

Induction of Single-Handed Helicity of Polyacetylenes Using Mechanically Chiral Rotaxanes as Chiral Sources

Induction of Single-Handed Helicity of Polyacetylenes Using Mechanically Chiral Rotaxanes as Chiral Sources
Toshikazu Takata, Yasuhito Koyama, Kazuko Nakazono, Fumitaka Ishiwari
Effective induction of preferred-handed helicity of polyacetylenes by pendant mechanically chiral rotaxanes is discussed. Polyacetylenes possessing optically active mechanically chiral rotaxanes in the side chains were synthesized by the polymerization of the corresponding enantiopure [2]rotaxane-type ethynyl monomers prepared by the chiral-phase HPLC separations. The CD Cotton effects revealed that the polyacetylenes took preferred-handed helical conformations depending on the rotaxane chirality. The preferred-handed helix was not disturbed by an additional chiral substituent on the rotaxane side chain. These results demonstrate the significance and utility of mechanically chiral rotaxanes for the effective construction of asymmetric fields. Mechanically chiral compounds are utilized as a chiral source. Polyacetylenes with optically active mechanically chiral rotaxanes in the side chains show strong circular dichroism on the main-chain absorption regions, indicating that the rotaxanes efficiently induce helicity with preferred handedness. These results demonstrate the significance and utility of mechanically chiral rotaxanes for the construction of asymmetric fields.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201707926

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