Amphiphilic polymers comprising of conjugated polyacetylene backbone and naturally occurring pendants: synthesis, chain helicity, self-assembling structure, and biological activity

Functional acetylenes containing naturally occurring building blocks of amino acids, monosaccharides, and nucleosides were effectively polymerized by organorhodium catalysts into stereoregular polymers of high molecular weights in high yields. Most of the polymers were completely soluble, and their solutions exhibited unique solvatochromism. The chiral pendants induced the polyacetylene chains to helically rotate and the chain helicity were continuously and reversibly tunable by such external stimuli as solvent, temperature, pH, and additive. The amphiphilic macromolecular chains cooperatively assembled into hierarchical structures including spherical vesicles, twisting cables, and helical nanotubes, in which the intra- and interstrand hydrogen bonding played an important role. All the polymers were cytocompatible. The monosaccharide-containing polymers were cytophilic and stimulated the growth of living cells.