Synthesis of de-crosslinkable polyamide having hexaarylbisimidazolyl moieties.

Abstract The ε -caprolactam monomer having a triphenylimidazole moiety such as DL-3-[ α -4-(4,5-diphenyl-1 H -imidazole-2-yl)-phenylacryloyl-amine]- ε -caprolactam (1) was synthesized by the Heck reaction of 2-(4-bromophenyl)-1-(methoxymethyl)-4,5-diphenylimidazole and the ε -caprolactam derivative having an acryloyl group in a good yield. The copolymerization of 1 and ε -caprolactam was carried out at 250 °C by using H 2 O as an initiator to give copolymer (4) in a good yield. The crosslinking reaction of the obtained 2 proceeded with K 3 [Fe(CN) 6 ] and KOH in a mixed solvent of ethanol and phenol. The resulting crosslinked polymer (5) was de-crosslinked under irradiation with visible light. Consequently, the thiol-capped de-crosslinked polymer (6) was obtained in a good yield. Graphical abstract Image 1 Highlights • The ε -caprolactam monomer having a triphenylimidazole moiety was synthesized by Heck reaction. • The copolymer having a triphenylimidazole moiety was prepared at 250 °C by using H 2 O as an initiator. • The crosslinking reaction of the obtained copolymer proceeded with K 3 [Fe(CN) 6 ] and KOH. • The resulting crosslinked polymer was de-crosslinked under irradiation with visible light. [ABSTRACT FROM AUTHOR]