Optically active polymers bearing side-chain photochromic moieties: synthesis and chiroptical properties of methacrylic homopolymers with pendanttrans-azobenzene chromophores bound throughL-leucine,L-valine andL-proline amino acid spacers

Abstract

Novel optically active monomers, based on different L-amino acid residues such as trans-(S)-4-(2-methacryloylamino-3-methylbutanoylamino)azobenzene and trans-(S)-4-( N-methacryloyl-2-pyrrolidinoylamino)azobenzene, have been prepared and homopolymerizd by free radical initiation. Circular dichroism spectra of the resulting polymers, as compared with those of the corresponding low molecular weight analogues, purposely synthesized, allow one to suggest that the macromolecules assume in solution achiral or chiral conformations with a prevailing screw sense, depending on the bulkiness and rigidity of the L-amino acid residue present in the side chains. The role of intra- and/or intermolecular hydrogen bonding between side-chain amido groups along the backbone and the structural requirements of the chiral groups in determining the macromolecular arrangement in also discussed.