S. Habaue, Tomoaki Seko, Y. Okamoto
Nov 1, 2003
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0
Influential Citations
14
Citations
Journal
Polymer
Abstract
Abstract The oxidative coupling polymerization of racemic -, ( R )-, and ( S )-2,2′,3,3′-tetrahydroxy-1,1′-binaphthyl derivatives bearing a crown ether moiety was carried out in the presence of a Cu(I) or Cu(II) catalyst with various ligands, such as N , N , N ′, N ′-tetramethylethylenediamine, ( S )-(+)-1-(2-pyrrolidinylmethyl)pyrrolidine, (−)-sparteine [(−)Sp], and ( S )-(−)-2,2′-isopropylidenebis(4-phenyl-2-oxazoline). Methanol-insoluble poly(binaphthyl crown ether) with a molecular weight up to M n =4.1×10 3 was synthesized in moderate yields. Polymerization using (−)Sp proceeded in an S -selective manner; the polymer with the highest negative specific rotation was obtained with the ( S )-monomer. The obtained polymers exhibited characteristic abilities for chiral recognition toward amino acids, such as 2-phenylglycine hydrochloride and 2-phenylglycine methyl ester hydrochloride.