Summary
The polymerizations of three nitrogen-containing heterophanes such as [2.2](2,5)pyridinophane (1), [2.2](2,5)pyrazinophane (2) and N, N′-dimethyl-[2.2](2,5)pyrrolophane (3) by the vapor deposition method were carried out. Compounds1, 2 and3 gave poly(2,5-pyridinediyl-ethylene), poly(2,5-pyrazinediylethylene), and poly(N-methyl-2,5-pyrrolediyl-ethylene) as tough films, respectively. The transformation of the ethylene unit in the polymer films to the vinylene one by the dehydrogenation reaction using 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) failed in the former two polymeric films and succeded to a certain extent in the latter one. The electrical conductivity of a poly(N-methyl-2,5-pyrrolediyl-vinylene) film obtained by the dehydrogenation reaction was measured to be 4×10-4 S/cm at room temperature and increased up to 1×10-2 S/cm on doping with iodine.
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Itoh, T., Iwasaki, T., Kubo, M. et al. Polymerizations of nitrogen-containing heterophanes by vapor deposition method, transformation to polymeric films bearing a conjugated structure, and their properties. Polymer Bulletin 35, 307–313 (1995). https://doi.org/10.1007/BF00963128
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DOI: https://doi.org/10.1007/BF00963128