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Novel Optically Active Polyacetylenes: Synthesis and Helical Conformation of L ‐Lysine‐Dendronized Poly(phenylacetylene)
Author(s) -
Zhao Haichao,
Sanda Fumio,
Masuda Toshio
Publication year - 2006
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.200600259
Subject(s) - phenylacetylene , chemistry , polymer chemistry , polymerization , side chain , solvent , peptide , circular dichroism , lysine , polymer , specific rotation , peptide synthesis , helix (gastropod) , stereochemistry , catalysis , organic chemistry , amino acid , biochemistry , ecology , snail , biology
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.