Synthesis and properties of helical polyacetylenes containing carbazole |
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Authors: | Jinqing Qu Toshio Masuda |
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Affiliation: | Department of Polymer Chemistry, Graduate School of Engineering, Kyoto University, Katsura Campus, Kyoto 615-8510, Japan |
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Abstract: | Novel acetylene monomers containing carbazole with chiral menthyl and bornyl groups, 9-(1R,2S,5R)-menthyloxycarbonyl-2-ethynylcarbazole (1), 9-(1S,2R,5S)-menthyloxycarbonyl-2-ethynylcarbazole (2), 9-(1R,2S,5R)-menthyloxycarbonyl-3-ethynylcarbazole (3) and 9-(1S)-bornyloxycarbonyl-2-ethynylcarbazole (4) were synthesized and polymerized with a Rh catalyst to give the corresponding polymers poly(1)-poly(4)] with moderate Mn value of (11.5-92.2) × 103 in good yields (77-89%). CD spectroscopic studies revealed that poly(1), poly(2) and poly(4) took predominantly one-handed helical structure in CHCl3, THF, toluene, and CH2Cl2, while poly(3) did not. Addition of methanol to CHCl3 solutions of poly(1) and poly(2) resulted in the formation of aggregates showing smaller CD signals at 275 and 320 nm. The helical structure of poly(1) and poly(2) was very stable against heating. The polymers emitted fluorescence in 0.40-2.90% quantum yields. Poly(4) exhibited an obvious oxidation peak at 1.10 V. The polymers were thermally stable below 300 °C. |
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Keywords: | Carbazole Helical polymers Polyacetylenes |
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