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Methacrylic Polymers Containing Optically Active Side-Chain Carbazole: Synthesis, Characterization and Photoconductive Properties

✍ Scribed by Luigi Angiolini; Tiziana Benelli; Loris Giorgini; Attilio Golemme; Francesco Mauriello; Elisabetta Salatelli; Roberto Termine

Publisher
John Wiley and Sons
Year
2008
Tongue
English
Weight
258 KB
Volume
209
Category
Article
ISSN
1022-1352

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✦ Synopsis

Abstract

Two novel optically active polymethacrylates bearing in the side chain a cyclic chiral group of one prevailing absolute configuration linked to the carbazole chromophore, deriving from the related monomers (S)‐(−)‐3‐methacryloyloxy‐N‐[3‐(9‐ethylcarbazolyl)]pyrrolidine [(S)‐(−)‐MECP] and (S)‐(+)‐2‐methacryloyloxy‐N‐[3‐(9‐ethylcarbazolyl)]succinimide [(S)‐(+)‐MECSI], have been prepared and characterized with the aim to obtain materials suitable to photoconductive applications. Poly[(S)‐(−)‐MECP] and poly[(S)‐(+)‐MECSI] exhibit remarkable thermal stability, with glass transition temperature around 200 °C and decomposition temperatures in the range 330–350 °C. Spectroscopic, thermal and chiroptical characterizations indicate the occurrence of dipolar interactions among the side chain moieties and the presence of chiral conformation at least for chain segments of the macromolecules. The photoconductive properties are discussed in terms of extent of conjugation in the side chain based on the electron‐acceptor or electron‐donator properties of the optically active ring linked to the carbazole group.

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