Chiroptical polymers are interesting due to diverse applications
in the field of chromatography, biomedicines, and catalysis. This
study describes the synthesis of new types of optically active polymers
of vitamin B5 analogous methacrylamide (B5AMA) using a photoiniferter
polymerization approach at ambient temperatures. Enantiomers of B5AMA
monomer ((R) and (S)) were prepared
by the ring opening method and were characterized for their optical
activity. The monomers were then polymerized by a photoiniferter polymerization
approach using two different thiocarbonylthio (TCT) compounds as iniferters.
Both TCTs showed controlled polymerization of B5AMA enantiomers and
yielded polymers of opposite optical rotation. The enantiomeric polymers
of B5AMA exhibited a complementary mirror-image Cotton effect to each
other in the circular dichroism (CD) spectra, and 13C NMR
analysis revealed the formation of syndiotactic polymer structures.
To the best of our knowledge, this is the first study that depicts
the successful synthesis of optically active macromolecules by a photoiniferter
polymerization approach.
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