The dawn of chiral material development using saccharide-based helical polymers

Abstract

Polysaccharides, such as cellulose and amylose, are abundant and optically active carbohydrate-based resources. Their suitably modified derivatives (for example, benzoate and phenylcarbamate derivatives) exhibit excellent resolution abilities for a wide variety of chiral compounds when applied to chiral stationary phases (CSPs) for high-performance liquid chromatography. Despite the established application of polysaccharides in CSP materials, their use in other chiral functional materials has been limited. In this review, the author describes the functionalization of cellulose and amylose to yield novel chiral functions other than those in CSPs, as well as the use of these materials for various applications, such as asymmetric organocatalysts, chiral auxiliaries and chiral fluorescent sensors. The synthesis of a saccharide-containing polymer via the polymerization of a glucose-based monomer and its application as a circularly polarized luminescence material are also described. The author has recently focused on exploring novel possibilities of cellulose and amylose, which exist in great abundance on earth. In this review, the author describes the functionalization of cellulose and amylose to give novel chiral functions other than that as chiral stationary phases and their use in applications, such as asymmetric organocatalysts, chiral auxiliaries and chiral fluorescent sensors. Furthermore, the application of a saccharide-containing helical polymer, which can be prepared through polymerization of a glucose-based monomer, to a circularly polarized luminescence material is also described.