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Optically Active Methacrylic Copolymers Bearing Side-Chain Bisazoaromatic and Bulky Achiral Moieties

✍ Scribed by Luigi Angiolini; Tiziana Benelli; Loris Giorgini; Francesco Mauriello; Elisabetta Salatelli

Publisher
John Wiley and Sons
Year
2007
Tongue
English
Weight
215 KB
Volume
208
Category
Article
ISSN
1022-1352

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✦ Synopsis

Abstract

The synthesis of two novel series of optically active methacrylic copolymers that contain a side‐chain chiral moiety linked to a photochromic bisazoaromatic chromophore has been carried out by radical copolymerization of the monomer (S)‐3‐methacryloyloxy‐1‐[4′‐phenylazo‐(4‐azobenzene)]pyrrolidine with highly sterically hindered monomers such as __tert‐__butyl methacrylate or triphenylmethyl methacrylate with the aim to investigate the effect on the optical activity of the resulting derivatives. The copolymeric products have been fully characterized and their spectroscopic and thermal properties compared to those of the related optically active homopolymer and the copolymers with methyl methacrylate, previously reported.

The optical activity displayed by the polymers is discussed in terms of extent of chiral conformations assumed by the macromolecules as a consequence of the insertion of co‐monomers capable of affecting the dipole‐dipole interactions that occur in these derivatives between the side‐chain bisazoaromatic chromophores disposed according to a mutual chiral arrangement.

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Experimental part ## Chemicals, monomers and models Methacryloyl chloride (Aldrich) was distilled (b. p. 95 8C) under inert atmosphere in the presence of traces of 2,6-ditert-butyl-p-cresol as polymerization inhibitor just before