Enantioselective synthesis of helical polydiacetylene by application of linearly polarized light and magnetic field

Abstract

Magnetic optical activity, which can occur in all media and is induced by longitudinal magnetic field, causes the difference in absorption coefficients of left and right circularly polarized light and has the potential for magnetically induced enantioselectivity in chemical reactions. Compared with the well-established technique with circularly polarized light, there are few reports on the production of helical conjugated polymers in a photochemical reaction based on above magnetochiral anisotropy mechanism. Herein, we demonstrate experimentally that the enantioselective polymerization of diacetylene derivative can be achieved in the liquid crystal phase by application of linearly polarized light under a parallel or antiparallel magnetic field. The screw direction of predominant helical polydiacetylene chain can be rigorously controlled with the relative orientation of linearly polarized light and the magnetic field. Moreover, the prepared helical polydiacetylene assemblies can serve as a direct visual probe for the enantioselective recognition of D-or L-lysine.

Dispersion Polymerization of Substituted Acetylenes in the Presence of Chiral Source for Preparing Monodispersed Chiral Nanoparticles

“…Substituted polyacetylenes can adopt helical structures under appropriate conditions. The macromolecular helical structures can be analyzed by circular dichroism (CD) and UV–vis absorption spectroscopy measurements . Noteworthily, the optical activity of substituted polyacetylenes can be quantitatively measured in solution state, but only qualitative characterizations can be performed on the products in the form of particles.…”

Seed‐Surface Grafting Precipitation Polymerization for Preparing Microsized Optically Active Helical Polymer Core/Shell Particles and Their Application in Enantioselective Crystallization

“…Circular dichroism (CD) and UV–vis absorption spectroscopies are effective techniques for identifying the helical structures and optical activities of substituted polyacetylenes in both solution and particle forms . However, only qualitative characterization can be performed on the particles so far.…”

Induction of Supramolecular Helical Handedness in a Chemical Reaction Directed Self‐Healable Soft Material

“…To induce the chirality within the supramolecular system, it is not necessary that the building block should be chiral. Sometimes achiral constituents can also provoke supramolecular chirality ,. However, chiral micro‐environments are fabricated with the use of chiral building blocks which offer an additional factor to induce chirality within the supramolecular system .…”