One of the greatest challenges in modern chemical processing is that of achieving enantiospecific control over molecular chirality. Discovering efficient methods to produce, control and identify enantiomerically pure chiral compounds is critical for the further development of many applications in various. In recent years chiral polymeric particles1-5 (micro and nano sizes) receives attention for their potential applications in many chiral processes such as stereoselective synthesis, separation of chiral compounds and optical activity. In this lecture we present novel approach4 for the preparation of chiral nano size polymeric particles based on miniemulsion polymerization of N-acryloyl amino acids monomers. In figure below the SEM images of this new type of chiral polymeric nanoparticles is shown. Using this approach we have prepared lager set of amino acids based chiral nanoparticles. Moreover we will present our results on the use of those chiral polymeric nanoparticles for few chiral applications such as chiral crystallization4 and stereoselective synthesis5.
Figure 1. SEM images of a) poly(L-Glu), b) poly(D-Glu), c) poly(L-Thr), d) poly(D-Thr), e) poly(L-Phe) and f) poly(D-Phe) nanoparticles.
References
1) Mastai, Y.; Sedlak, M.; Colfen, H.; Antonietti, M., The separation of racemic crystals into enantiomers by chiral block copolymers. Chemistry-A European Journal 2002, 8, 2430-2437. (2) Menahem, T.; Mastai, Y., Chiral soluble polymers and microspheres for enantioselective crystallization. Journal of Polymer Science Part a-Polymer Chemistry 2006, 44, 3009-3017. (3) Medina, D. D.; Goldshtein, J.; Margel, S.; Mastai, Y., Enantioselective crystallization on chiral polymeric microspheres. Advanced Functional Materials 2007, 17, 944-950. (4) Preiss, L. C.; Werber, L.; Fischer, V.; Hanif, S.; Landfester, K.; Mastai, Y.; Munoz-Espi, R., Amino-Acid-Based Chiral Nanoparticles for Enantioselective Crystallization. Advanced Materials 2015, 27 (17), 2728.( 5)Adler S.R.; Mastai Y. Chiral polymeric nanoparticles for aldol reaction, Reactive and Functional Polymers, 2015, 96, 1-4.