Abstract
7,7,8,8-Tetra-(methoxycarbonyl)-quinodimethane, TMQ, was synthesized in improved yield from tetramethyl p-phenylenedimalonate by forming the dianion of the latter with potassium hydride and oxidizing it with iodine. Free radical and anionic initiators gave homopolymer quantitatively. The homopolymer, m.p. 295–315° was insoluble in all solvents except for the strong acids, sulfuric, chlorosulfonic, and trifluoromethane-sulfonic acid, in which it exhibited polyelectrolyte viscosity behavior.
Free radical copolymerization with styrene using excess or equivalent TMQ in the feed gave only 1∶1 alternating copolymer, but excess styrene gave copoly mers richer in styrene. Other electron-rich comonomers: p-chlorostyrene, 2-vinylnaphthalene, p-methoxystyrene, N-vinylcarbazole, and isobutyl vinyl ether also gave alternating copolymers with TMQ, the latter two without added initiator. Less electron-rich vinyl compounds did not copolymerize.
TMQ possesses less electron affinity than TCNQ, as established by cyclic voltammetry and tests with donor molecules.
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Hall, H.K., Bentley, J.H. 7,7,8,8-Tetra-(methoxycarbonyl)-quinodimethane, a reactive electrophilic monomer. Polymer Bulletin 3, 203–210 (1980). https://doi.org/10.1007/BF00291958
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DOI: https://doi.org/10.1007/BF00291958