Journal
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY
Volume 48, Issue 23, Pages 5411-5418Publisher
WILEY-BLACKWELL
DOI: 10.1002/pola.24346
Keywords
chiral; enantioselective recognition; radical polymerization; rare-earth trifluoromethanesulfonates; stereospecific polymers
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Funding
- National Natural Science Foundation of China [21074107]
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Enantiopure acrylamide derivatives, N-[o-(4-methyl-4,5-dihydro-1,3-oxazol-2-yl) phenyl] acrylamide (MeOPAM), N-[o-(4-isopropyl-4,5-dihydro-1,3-oxazol-2-yl) phenyl] acrylamide (Pr(i)OPAM), and N-[o-(4-phenyl-4,5-dihydro-1,3-oxazol-2-yl) phenyl] acrylamide (PhOPAM), were synthesized and radically polymerized in the presence of rare earth metal trifluoromethanesulfonates (Ln(OTf)(3), Ln La, Nd, Sm, and Y) to yield corresponding optically active polymers. Among these Lewis acids, Y(OTf)(3) was found to be most effective for increasing the isotactic specificity during the radical polymerizations when using n-butanol as solvent. Also, the effect of the Lewis acids was significantly influenced by the ratio of Ln(OTf)(3) to monomer. The relationship of both chiroptical property and the chiral recognition with the stereoregularity was then examined for the resulting polymers having various tacticity by spectroscopic techniques such as NMR, fluorescence, and circular dichroism. The results indicated that the polymers rich in isotacticity exhibited a favorable enantioselective discrimination ability toward 1,1'-bi-2-naphthol as evidenced by H-1 NMR study, where the characteristic hydroxyl proton signal was split into two peaks that ascribed respectively to the levo-and dextro-isomer; furthermore, the splitting magnitude was linearly correlated with the diad isotacticity of the polymers. (C) 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 48: 5411-5418, 2010
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