Synthesis and properties of ornithine- and lysine-based poly(N-propargylamides). Responsiveness of the helical structure to acids

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• 作者：Ruiyuan Liu ; Fumio S ; a ; Toshio Masuda
• 关键词：Helix ; pH-responsiveness ; Polyacetylene
• 刊名：Polymer
• 出版年：2007
• 出版时间：19 October 2007
• 年：2007
• 卷：48
• 期：22
• 页码：6510-6518
• 全文大小：752 K

文摘

Ornithine- and lysine-based novel N-propargylamides, N-α-tert-butoxycarbonyl-N-δ-fluorenylmethoxycarbonyl-l-ornithine-N′-propargylamide (1), N-α-tert-butoxycarbonyl-N--fluorenylmethoxycarbonyl-l-lysine-N′-propargylamide (2), N-α-fluorenylmethoxycarbonyl-N-δ-tert-butoxycarbonyl-l-ornithine-N′-propargylamide (3), and N-α-fluorenylmethoxycarbonyl-N--tert-butoxycarbonyl-l-lysine-N′-propargylamide (4) were synthesized and polymerized with a rhodium catalyst. Polymers with moderate molecular weights were obtained in good yields. Poly(1)–poly(4) showed strong Cotton effects in THF, whose sign and wavelength depended on the substituents. They were satisfactorily converted into the corresponding polymers [poly(1a)–poly(4a)] with free amino groups. Poly(1a) and poly(2a) also formed a helix, while poly(3a) and poly(4a) did not. Poly(1a) and poly(2a) decreased the CD intensity by the addition of m- and o-phthalic acids.