Dual memory of enantiomeric helices in a polyacetylene induced by a single enantiomer.
We report the dual memory of both the enantiomeric right- and left-handed helical conformations induced in a polyacetylene based on the temperature-stimulated helicity inversion of the polymer. The polyacetylene folds into a one-handed helix induced by noncovalent bonding interactions with a single enantiomeric amine. The induced helix underwent a reversible inversion of the helicity by temperature. The diastereomeric right- and left-handed helices obtained at different temperatures could be further memorized when the optically active amine was replaced by an achiral diamine, generating right- and left-handed helices of the mirror images of each other. Consequently, both enantiomeric helices can be produced with a high efficiency from dynamically diastereomeric helical polyacetylenes induced by a single enantiomer.
Miyagawa
Toyoharu
T
Yashima Super-structured Helix Project, Exploratory Research for Advanced Technology (ERATO), Japan Science and Technology Agency (JST), Creation Core Nagoya 101, Nagoya 463-0003, Japan.
Furuko
Akira
A
Maeda
Katsuhiro
K
Katagiri
Hiroshi
H
Furusho
Yoshio
Y
Yashima
Eiji
E
D000114:Acetylene / Q000031:analogs & derivatives* / Q000737:chemistry*; D040761:Biomimetic Materials / Q000737:chemistry; D002942:Circular Dichroism; D005021:Ethylamines / Q000737:chemistry; D008968:Molecular Conformation; D009281:Naphthalenes / Q000737:chemistry; D063065:Organophosphonates / Q000737:chemistry; D011108:Polymers / Q000737:chemistry*; D053279:Polyynes; D017550:Spectroscopy, Fourier Transform Infrared; D013237:Stereoisomerism
D005021:Ethylamines; D009281:Naphthalenes; D063065:Organophosphonates; D011108:Polymers; D053279:Polyynes; C055450:1-(1-naphthyl)ethylamine; D000114:Acetylene