Polymerization of optically active 2-fluorophenyl-4-fluorophenyl-2-pyridylmethyl methacrylate with anionic and radical initiators: Stereospecificity and helix-sense selection

✍ Scribed by Jian Wu; Tamaki Nakano; Yoshio Okamoto

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 112 KB
• Volume: 37
• Category: Article
• ISSN: 0887-624X
• DOI: 10.1002/(sici)1099-0518(19990715)37:14<2645::aid-pola39>3.0.co;2-7

✦ Synopsis

Almost optically pure (ϩ)-and (Ϫ)-2-fluorophenyl-4-fluorophenyl-2-pyridylmethyl methacrylate (2F4F2PyMA) monomers were obtained by HPLC resolution of the racemic monomer and polymerized with the use of anionic and free-radical initiators. Helix-sense selectivity during the polymerization seemed to be governed mainly by the chirality of the monomer itself, and the polymers obtained by using the complex of N,NЈ-diphenylethylenediamine monolithium amide with (S)-(ϩ)-1-(2-pyrrolidinylmethyl)pyrrolidine (PMP) in toluene at Ϫ78°C appeared to possess single-handed helical conformation

The single-handed helical (ϩ)-poly[(Ϫ)-2F4F2PyMA] and (Ϫ)-poly[(ϩ)-2F4F2PyMA] obtained with the PMP complex exhibited better chiral recognition ability toward trans-stilbene oxide compared with the single-handed helical poly(rac-2F4F2PyMA) prepared previously.