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Synthesis of well-defined poly(p-benzamide) from chain-growth polycondensation and its application to block copolymers |
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| Authors: | Tsutomu Yokozawa Miyuki Ogawa Atsushi Sekino Ryuji Sugi Akihiro Yokoyama |
| Institution: | 1. Department of Applied Chemistry, Kanagawa University, Rokkakubashi, Kanagawa-ku, Yokohama 221-8686, Japan;2. Department of Applied Chemistry, Kanagawa University, Rokkakubashi, Kanagawa-ku, Yokohama 221-8686, Japan
“Synthesis and Control”, PRESTO, Japan Science and Technology Corporation (JST), Japan |
| Abstract: | Poly(p-benzamide) with a defined molecular weight and a low polydispersity and block copolymers containing this well-defined aramide was synthesized. Phenyl 4-(4-octyloxybenzylamino)benzoate ( 1b ) polymerized at room temperature in the presence of base and phenyl 4-nitrobenzoate ( 2a ) as an initiator in a chain-growth polycondensation manner to give well-defined aromatic polyamides having the 4-octyloxybenzyl groups as a protecting group on nitrogen in an amide. It was confirmed by a model reaction that deprotection of this protecting group proceeded completely with trifluoroacetic acid (TFA) without breaking the amide linkage. The utility of this approach to poly(p-benzamide) with a low polydispersity was demonstrated by the synthesis of block copolymers of poly(p-benzamide) and poly(N-octyl-p-benzamide) or poly(ethylene glycol). The SEM images of the supramolecular assemblies of the former block copolymer showed μm-sized bundles and aggregates of flake structures. |
| Keywords: | block copolymer chain-growth polycondensation living polymerization polyamide self-assembly |