Amide transformation as an efficient postpolymerization modification approach for the synthesis of functional polyacetylenes

文献情報

出版日 2020-04-21

DOI 10.1039/D0PY00398K

インパクトファクター 5.582

著者

Heng Liu, Xuequan Zhang, Yanming Hu, Guangyuan Zhou, Toshio Masuda

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要旨

Postpolymerization modification based on selective amide transformation reactions is explored for the preparation of functional polymers, since amides are an important building motif ubiquitously present in biological and synthetic polymers. Inspired by recent advances in amide chemistry, a N,N-Boc2-benzamide group-containing polyacetylene (P1) was synthesized and used as a polymer substrate for polymer modification. Transamidation of P1 using amine nucleophiles, (R)- and (S)-1-phenylethanamine and anthracen-9-ylmethanamine, proceeded completely at 30 °C under metal-free conditions to produce polymers featuring predominantly one-handed helical structures and enhanced luminescence (P1a–P1c). The reaction with alcohols needed more forcing conditions (at 60 °C with DMAP as the catalyst) to eventually achieve full substitution. Incorporation of 2-(2-(2-methoxyethoxy)ethoxy)ethanol led to a dramatic increase in the surface energy of P1d. P1e obtained using 4-hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl exhibited reversible charge/discharge ability as a cathode material in a Li-ion battery.

掲載誌

Polymer Chemistry

CiteScore: 8.6

自己引用率: 7.3%

年間論文数: 457

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Amide transformation as an efficient postpolymerization modification approach for the synthesis of functional polyacetylenes

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