A Novel Synthetic Route to Redox-Active Oligo(thio-1,4-phenylene) Derivatives via a Michael-Type Addition

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  • Kimihisa Yamamoto
    Department of Chemistry, Faculty of Science & Technology, Keio UniversityYokohama 223-8522
  • Masayoshi Higuchi
    Department of Chemistry, Faculty of Science & Technology, Keio UniversityYokohama 223-8522
  • Toyohiko Nishiumi
    Department of Chemistry, Faculty of Science & Technology, Keio UniversityYokohama 223-8522
  • Hirokazu Takai
    Department of Chemistry, Faculty of Science & Technology, Keio UniversityYokohama 223-8522

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<jats:title>Abstract</jats:title> <jats:p>N,N′-Diphenyl-1,4-benzoquinone diimine (PBI), which is the minimum redox-active unit of polyaniline, was reduced to N,N′-diphenyl-1,4-phenylenediamine (PDA) derivatives through Michael-type additions of some nucleophiles. The addition of thiophenol to PBI proceeded very rapidly. The polyaddition of PBI-endcapped monomers (P-2PBI, B-2PBI, and TB-2PBI) with thiobisbenzenethiol (TB) produced the novel thermostable oligo(thio-1,4-phenylene)s (OTP) having PDA units as a redox-active site (OTP-P-PDA, OTP-B-PDA, and OTP-PDA). This polymerization proceeded at room temperature without catalysts. OTP-P-PDA, one of the oligomers obtained, was found to have a moderate molecular weight (Mw 8400) and to possess good thermostability (Td10% 400 °C). The polymerization based on Michael-type additions was also confirmed by NMR measurements. The oligomers obtained behaved as good electro-responsive materials. The redox process was determined by the slope of the Nernst plot that involved two electrons and two protons per PDA unit.</jats:p>

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