Electrosyntheses and characterization of polyalkylenedioxybenzenes |
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Authors: | Houting Liu Yuzhen Li Zhanggao Le Mingbiao Luo Shouzhi Pu |
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Institution: | a Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, Nanchang 330013, China b College of Chemistry, Biology and Material Science, East China Institute of Technology, 56 Xuefu Road, Fuzhou 344000, China c College of Chemistry and Molecular Science, Wuhan University, Wuhan 430072, China |
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Abstract: | Direct anodic oxidation of 1,2-methylenedioxybenzene (MDOB) and 1,2-ethylenedioxybenzene (EDOB), analogues of 3,4-alkylenedioxythiophene and 3,4-alkylenedioxypyrrole, led to the formation of polyacetylene derivatives, poly(1,2-methylenedioxybenzene) (PMDOB) and poly(1,2-ethylenedioxybenzene) (PEDOB), on a platinum sheet in pure boron trifluoride diethyl etherate (BFEE). IR, 1H NMR, 13C NMR and quantum chemistry calculations confirmed that the polymerization occurred at C(4) and C(5) position on the benzene ring of the monomer, making the main backbone of PMDOB and PEDOB similar to polyacetylene. Both dedoped PMDOB and PEDOB in DMSO solution showed good fluorescence properties with quantum yields of 0.13 and 0.27, emitting blue and green light under excitation of 365 nm, respectively. PMDOB showed electrochromic properties from grass green (doped) to light nacarat (dedoped). PEDOB changed it from bottle green (doped) to nacarat (dedoped). Doped PMDOB and PEDOB own electrical conductivities of 0.1 S cm−1 and 0.17 S cm−1, respectively. |
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Keywords: | Conducting polymers Electrochemical polymerization Poly(para-phenylene) Polythiophene PEDOT |
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