3.1. Preparation of polymers containing N-phenyl-2,6-
dimethoxybenzamide group for Li ion conductivity measurement
At first, as a straightforward application of the reported polymer structure of poly[2,6-dimethoxy-N-(4-vinylphenyl)benzamide] poly1, we tried to prepare and polymerize diazoacetate monomer 4, with the N-phenylbenzamide group directly attached to the ester group in the diazocarbonyl moiety in place of the styrenic C_C in 1 (Scheme 1). However, preliminary attempts for the polymerization of 4 revealed the low polymerizability of 4, resulting in no polymer formation from 4 using standard conditions for our Pd-initiated polymerization of diazoacetates. We attributed the results to the low reactivity and low solubility of both the monomer and propagating polymeric species, owing to the direct connection between the N-phenylbenzamide and ester groups. Accordingly, in order to improve the reactivity and solubility, we incorporated an ethylene (–CH2CH2–) spacer between the Nphenylbenzamide and ester groups; the synthetic scheme for the modified monomer 2 is shown in Scheme 2, where the silyl-protected 4-(2hydroxyethyl)aniline 6 was acylated with 2,6-dimethoxybenzoic acid, followed by diazoacetylation of the deprotected alcohol 10 affording 2. Likewise, acrylate type monomer 3 for the synthesis of a vinyl polymer counterpart poly3 was prepared by the reaction of acryloyl chloride with the deprotected alcohol 10.