Helix-Sense-Selective Permeation of Racemic Helical Oligoacetylenes through One-Handed Helical Channels in Polymer Membranes.

Helix-sense-selective permeation (HSSPerm) of racemic helical oligoacetylenes through one-handed helical channels has been realized. The one-handed helical channels were created in the one-handed helical polyacetylene membranes by the helix-sense-selective decomposition (HSS-SCAT) of the corresponding racemic helical polyacetylene membranes, followed by removing the formed oligomers. Since the HSS-SCAT reaction proceeds with just circularly polarized visible light with no reagents, no catalysts, no solvent, and high selectivity, the chiral channel-containing membrane with high purity was obtained easily. This membrane could separate racemic helical oligoacetylenes enantioselectively in up to 30%ee. To our knowledge, this is the first example of HSSPerm.