Carbazole has attracted considerable interest as building block in material science for its well known hole-transporting and electroluminescence properties [1]. Since the discovery of the photoconductive character of poly(N-vinylcarbazole) (PVK), carbazole containing polymers [2] have attracted much attention because of their unique features. The use of these material in advanced micro- and nanotechnologies spreads in many different applications such as photoconductive polymers, electroluminescent devices, programmable optical interconnection, data storage, chemical photoreceptors, NLO, surface relief gratings, blue emitting materials, holographic memory. On the other hand, an intense interest has currently arisen toward investigations dealing with the amplification of chirality of polymeric materials, in solution as well as in the solid state [3]. Two novel optically active polymethacrylates bearing in the side chain a chiral group of one prevailing absolute configuration linked in 3 position to the carbazole chromophore, deriving from the chiral monomers (S)-(−)-methacryloyl-2-oxy-N-[3-(9-ethylcarbazole)]-pyrrolidine [(S)-(−)-MECP] and (S)-(−)-methacryloyl-2-oxy-N-[3-(9-ethylcarbazole)]-succinimide [(S)-(+)-MECSI] have been prepared and characterized with the aim to improve the conformational order of the macromolecules and investigate the influence of the intrinsic macromolecular chirality on their photoconductive and photorefractive properties. Spectroscopic, thermal and chiroptical characterizations indicate the occurrence of dipolar interactions between side chain moieties and the presence of an ordered chiral conformations, at least for chain segments of the macromolecules, that influence their photoconductive properties. [1] J.V. Grazuleviciusa, P. Strohrieglb, J. Pielichowskic, K. Pielichowski, Prog. Polym. Sci. 28 (2003) 1297–1353 [2] K. Meerholz, B. Volodin, B. Sandalphon, N. Kippelen, N. Peyghambarian, Nature 1994, 371, 497 [3] M.M. Green, N.C. Peterson, T. Sato, A. Teramoto, R. Cook, S. Lifson, Science, 1995, 268, 1860
L. Angiolini, T. Benelli, L. Giorgini, A. Golemme, F. Mauriello, E. Salatelli, et al. (2007). SYNTHESIS, PHYSICO-CHEMICAL AND PHOTOCONDUCTIVE PROPERTIES OF METHACRYLIC POLYMERS CONTAINING SIDE-CHAIN CARBAZOLE. FIRENZE : INSTM.
SYNTHESIS, PHYSICO-CHEMICAL AND PHOTOCONDUCTIVE PROPERTIES OF METHACRYLIC POLYMERS CONTAINING SIDE-CHAIN CARBAZOLE
ANGIOLINI, LUIGI;BENELLI, TIZIANA;GIORGINI, LORIS;MAURIELLO, FRANCESCO;SALATELLI, ELISABETTA;
2007
Abstract
Carbazole has attracted considerable interest as building block in material science for its well known hole-transporting and electroluminescence properties [1]. Since the discovery of the photoconductive character of poly(N-vinylcarbazole) (PVK), carbazole containing polymers [2] have attracted much attention because of their unique features. The use of these material in advanced micro- and nanotechnologies spreads in many different applications such as photoconductive polymers, electroluminescent devices, programmable optical interconnection, data storage, chemical photoreceptors, NLO, surface relief gratings, blue emitting materials, holographic memory. On the other hand, an intense interest has currently arisen toward investigations dealing with the amplification of chirality of polymeric materials, in solution as well as in the solid state [3]. Two novel optically active polymethacrylates bearing in the side chain a chiral group of one prevailing absolute configuration linked in 3 position to the carbazole chromophore, deriving from the chiral monomers (S)-(−)-methacryloyl-2-oxy-N-[3-(9-ethylcarbazole)]-pyrrolidine [(S)-(−)-MECP] and (S)-(−)-methacryloyl-2-oxy-N-[3-(9-ethylcarbazole)]-succinimide [(S)-(+)-MECSI] have been prepared and characterized with the aim to improve the conformational order of the macromolecules and investigate the influence of the intrinsic macromolecular chirality on their photoconductive and photorefractive properties. Spectroscopic, thermal and chiroptical characterizations indicate the occurrence of dipolar interactions between side chain moieties and the presence of an ordered chiral conformations, at least for chain segments of the macromolecules, that influence their photoconductive properties. [1] J.V. Grazuleviciusa, P. Strohrieglb, J. Pielichowskic, K. Pielichowski, Prog. Polym. Sci. 28 (2003) 1297–1353 [2] K. Meerholz, B. Volodin, B. Sandalphon, N. Kippelen, N. Peyghambarian, Nature 1994, 371, 497 [3] M.M. Green, N.C. Peterson, T. Sato, A. Teramoto, R. Cook, S. Lifson, Science, 1995, 268, 1860I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
