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Synthesis and chiroptical properties of optically active methacrylic polymers bearing the ( S )‐ and/or ( R )‐2‐hydroxysuccinimide moiety linked to the trans ‐azobenzene group in the side chain
Author(s) -
Angiolini Luigi,
Caretti Daniele,
Giorgini Loris,
Salatelli Elisabetta
Publication year - 2000
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/(sici)1521-3935(20000301)201:5<533::aid-macp533>3.0.co;2-e
Subject(s) - succinimide , azobenzene , side chain , chemistry , monomer , polymer chemistry , moiety , copolymer , imide , circular dichroism , polymer , polymerization , tetramer , pendant group , photochemistry , stereochemistry , organic chemistry , enzyme
The synthesis of novel optically active monomers, namely ( S )‐(+)‐ and ( R )‐(–)‐2‐methacryloyloxy‐ N ‐(4‐azobenzene)succinimide and ( S )‐(+)‐2‐methacryloyloxy‐ N ‐(4′‐nitro‐4‐azobenzene)succinimide, is described. The monomers have been radically polymerized to afford the corresponding optically active homopolymers, characterized by the presence of an optically active rigid succinimide ring in the side chain linked to the trans‐ azoaromatic system through the imide nitrogen atom. A series of copolymers containing both the enantiomeric monomers in different molar amounts, have also been prepared in order to observe possible effects on the optical activity of the resulting derivatives. The chiroptical and conformational properties of the polymers in solution have been investigated by circular dichroism measurements and compared with those of low molecular weight model compounds, purposely synthesized, with the aim to verify the existence of cooperative interactions between chromophoric groups disposed along the macromolecular chain according to dissymmetric conformations.