Optically Active Biobased Hollow Polymer Particles: Preparation, Chiralization, and Adsorption toward Chiral Amines

Abstract

The present work reports a new type of optically active biobased hollow polymer particles (OABHPs) starting from a commonly available biophenylpropene transanethole (ANE). To prepare the OABHPs, ANE and maleic anhydride (MAH) underwent precipitation copolymerization in the presence of particulate template as cores, thereby forming core/shell particles. Subsequently removing the cores provided hollow particles, which were then chiralized with chiral agents (R-and S-1-phenylethylamine) and (R-and Scyclohexyalethylamine) to fabricate the designed OABHPs. The as-prepared particles were characterized by SEM, TEM, elemental analysis, CD, and FT−IR measurements. The chiral particles' enantioselectivity was further explored by using them as chiral adsorbent toward D-and L-alanine and (−)-cinchonidine and (+)-cinchonine. The optically active hollow particles showed good enantiomeric excess (e.e.) toward racemic alanine. The study not only opens up a new approach for preparing chiral polymer materials, but also provides a versatile platform for making a full use of biomass to develop advanced functional materials.

Monodisperse Liquid Crystalline Polymer Shells with Programmable Alignment and Shape Prepared by Seeded Dispersion Polymerization

“…Polymer shells are of interest for use in drug delivery, − in separation of chiral mixtures, − and as a host for catalysts. − Among hollow particles, liquid crystalline (LC) polymer shells are particularly interesting, as the alignment of LC molecules gives rise to novel anisotropic functional properties. − Monodisperse LC polymer shells have been prepared using microfluidics; − however, preparing well-defined LC polymer shells with tunable alignment with dimensions smaller than 10 μm remains a challenge.…”