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Solid Phase Ring-opening Polymerization of Macrocyclic S-Aryl Thioesters Containing Terephthaloyl Structure

Department of Chemistry, Faculty of Engineering, Kanagawa University

Takashi Ide

Tadatomi Nishikubo

Department of Applied Chemistry, Faculty of Engineering, Kanagawa University Rokkakubashi, Kanagawa-ku, Yokohama 221-8686, Japan

We have studied synthesis and solid-state ring-opening polymerization of macrocyclic S-aryl thioesters, dimer p-BBDT-2, trimer p-BBDT-3, and tetramer p-BBDT-4 containing terephthaloyl structure. The targeted p-BBDT-2, p-BBDT-3, and p-BBDT-4 were prepared by the reaction of terephthaloyl chloride (TPC) with 4-tert-butyl-1,2-benzenedithiol (BBDT) using NaOH under phase transfer conditions. The macrocyclic trimer p-BBDT-3 was obtained preferentially in 81% yield by a reaction at a concentration of 1.0 mol 1^-1 in a mixture of aqueous NaOH and chloroform. The structures of the prepared macrocyclic S-aryl thioesters were well identified by IR, ¹H NMR, ¹³C NMR spectroscopies, MALDI-TOF MS, and elemental analysis. The solubility and thermal properties of p-BBDT-2, p-BBDT-3, and p-BBDT-4 were characterized. It was found that the ring-opening polymerization of p-BBDT-2, p-BBDT-3, and p-BBDT-4 without catalysts occurred in the solid state, and the corresponding poly(S-aryl thioester)s with moderate molecular weights were obtained. The behaviors of the polymerization of p-BBDT-3 and catalytic effect of potassium halides/dibenzo-18-crown-6 complexes were examined. It was also found that the poly(S-aryl ester) obtained by a solid-state polymerization had good thermal properties.

Key Words: Solid phase • ring-opening polymerization • macrocyclic S-Aryl thioester • terephthaloyl • poly(S-aryl thioester)

High Performance Polymers, Vol. 15, No. 2, 207-218 (2003)
DOI: 10.1177/0954008303015002005


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