Observation of optical activity in polythiourethane obtained by the controlled cationic ring‐opening polymerization of chiral cyclic thiourethane derived from serine

The secondary structure of an optically active polythiourethane [(? CH₂C*H(CO₂Me)NHCOS? )_n] was evaluated with ¹H NMR, IR, and circular dichroism (CD) spectroscopy. Hydrogen bonds between the carbonyl and NH groups in the thiourethane group constrained the main chain of the chiral polythiourethane precisely under the direction of chirality in the main chain, whereas the racemic polymer was also constrained but randomly. The secondary structure of the polythiourethane in CHCl₃ changed noticeably in the presence or absence of trifluoroacetic acid, which eliminated constraining intramolecular hydrogen bonds. IR spectroscopy suggested that the secondary structure was almost identical in solid and solution states. © 2005 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 43: 1554–1561, 2005