Novel Optically Active Polyacetylenes: Synthesis and Helical Conformation of L-Lysine-Dendronized Poly(phenylacetylene)

✍ Scribed by Haichao Zhao; Fumio Sanda; Toshio Masuda

• Publisher: John Wiley and Sons
• Year: 2006
• Tongue: English
• Weight: 159 KB
• Volume: 207
• Category: Article
• ISSN: 1022-1352
• DOI: 10.1002/macp.200600259

✦ Synopsis

Abstract

Summary: The novel chiral phenylacetylene (1) functionalized with an L‐lysine‐based dendritic peptide was synthesized and polymerized with Rh catalysts to afford the corresponding polymer [poly(1)] with moderate molecular weights in good yields. Poly(1) was soluble in common organic solvents including DMF, THF, CHCl~3~, AcOEt, and MeOH. The polarimetric and CD spectroscopic data indicate that poly(1) exists in a helical structure with predominantly one‐handed screw sense in THF and CHCl~3~. Poly(1) also assumes a helical structure in the solid state. This helical structure can be tuned by heat in CHCl~3~ or by the addition of a protic solvent to CHCl~3~ solutions.

Synthesis of chiral poly(phenylacetylene) bearing a L‐lysine‐based dendritic peptide in the side chain.

magnified imageSynthesis of chiral poly(phenylacetylene) bearing a L‐lysine‐based dendritic peptide in the side chain.