Cationic ring‐opening polymerization of novel 1,3‐dehydroadamantanes with various alkyl substituents: Synthesis of thermally stable poly(1,3‐adamantane)s |
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Authors: | Sotaro Inomata Yusuke Harada Yuya Nakamura Yosuke Uehara Takashi Ishizone |
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Institution: | Department of Organic and Polymeric Materials, Tokyo Institute of Technology 2‐12‐1‐S1‐13 Ohokayama, , Tokyo 152‐8552 Japan |
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Abstract: | Cationic ring‐opening polymerizations of 5‐alkyl‐ or 5,7‐dialkyl‐1,3‐dehydroadamantanes, such as 5‐hexyl‐ ( 4 ), 5‐octyl‐ ( 5 ), 5‐butyl‐7‐isobutyl‐ ( 6 ), 5‐ethyl‐7‐hexyl‐ ( 7 ), and 5‐butyl‐7‐hexyl‐1,3‐dehydroadamantane ( 8 ), were carried out with super Brønsted acids, such as trifluoromethanesulfonic acid or trifluoromethanesulfonimide in CH2Cl2 or n‐heptane. The ring‐opening polymerizations of inverted carbon–carbon bonds in 4–8 proceeded to afford corresponding poly(1,3‐adamantane)s in good to quantitative yields. Poly( 4–8 )s possessing alkyl substituents were soluble in 1,2‐dichlorobenzene, although a nonsubstituted poly(1,3‐adamantane) was not soluble in any organic solvent. In particular, poly( 8 ) exhibited the highest molecular weight at around 7500 g mol?1 and showed excellent solubility in common organic solvents, such as THF, CHCl3, benzene, and hexane. The resulting poly( 4–8 )s containing adamantane‐1,3‐diyl linkages showed good thermal stability, and 10% weight loss temperatures (T10) were observed over 400 °C. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013 , 51, 4111–4124 |
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Keywords: | cationic polymerization 1 3‐dehydroadamantane poly(1 3‐adamantane) ring‐opening polymerization thermal properties |
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