Four
N-(4-halogenophenyl)maleimides (4-Hal-PMI) monomers,
N-(4-fluorophenyl)maleimide (4FPMI),
N-(4-chlorophenyl)maleimide (4CPMI),
N-(4-bromophenyl)maleimide (4BPMI), and
N-(4-iodophenyl)maleimide (4IPMI) were synthesized and obtained as yellow needle crystals. A positive relationship between the Hammett’s substituent constants (σ) and
1H NMR chemical shifts (δ) of the vinylene protons of all 4-Hal-PMI were observed. Each anionic polymerization of 4-Hal-PMI with lithium
tert- butoxide took place at the vinylene moieties and gave the correspondent poly(4-Hal-PMI) in 27–50% yields after 24 h at -60°C. A negative relationship was seen between the yields of poly(4-Hal-PMI) and the Hammett’s σ of each substituent of 4-Hal-PMI.
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