Synthesis and characterization of a new conjugated aromatic poly(azomethine) derivative based on the 3′,4′-dibutyl-α-terthiophene building block

Chenggang Wang, Seaver Shieh, Eugene LeGoff, Mercouri G Kanatzidis

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Abstract

A new conjugated aromatic poly(azomethine) derivative, poly(3′,4′-dibutyl-α-terthiophene-azomethine-1,4-phenylene- azomethine) (PBTPI), has been prepared by polycondensation of 2,5″-diformyl-3′,4′-dibutyl-2,2′:5′,2″- terthiophene with 1,4-phenylenediamine under the ethanothermal conditions. The red polycrystalline PBTPI was characterized by X-ray diffraction, NMR, FTIR, UV-visible-near-IR, photoluminescence, and ESR spectroscopies. PBTPI is partially soluble in tetrahydrofuran, giving an orange solution with an absorption maximum (λmax) of 457 nm. In the solid state, PBTPI has an optical band gap of 2.06 eV, which is one of the lowest among poly(azomethines), and is highly sensitive to a strong acid environment. Protonation yields a blue polymer with an optical band gap of 1.61 eV. The polymer is completely soluble in concentrated sulfuric acid and nitromethane containing Lewis acids (e.g., AlCl3), giving blue solutions with λmax of 656 and 638 nm, respectively. Iodine-doped PBTPI shows low electrical conductivity at the order of 10-7-10-8 S/cm. The properties of PBTPI are compared to other, previously characterized, related polymers.

Original languageEnglish
Pages (from-to)3147-3156
Number of pages10
JournalMacromolecules
Volume29
Issue number9
Publication statusPublished - Apr 22 1996

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ASJC Scopus subject areas

  • Materials Chemistry

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