Electrosynthesis of highly conducting poly(1,5-dihydroxynaphthalene) in BF3·Et2O |
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Authors: | Baoyang Lu Jingkun Xu Zhanggao Le Huoyu Rao |
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Affiliation: | a Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, Nanchang 330013, Jiangxi Province, China b College of Chemistry, Biology and Material Science, East China Institute of Technology, Fuzhou 344000, Jiangxi Province, China |
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Abstract: | Direct anodic oxidation of 1,5-dihydroxynaphthalene (DHN), an important derivative of naphthalene, led to the formation of high-quality semiconducting poly(1,5-dihydroxynaphthalene) (PDHN) on stainless steel sheets in boron trifluoride diethyl etherate (BFEE). The onset oxidation potential of DHN in this medium was measured to be only 0.78 V vs. SCE, which was lower than that determined in traditional acetonitrile containing 0.1 mol/L tetrabutylammonium tetrafluoroborate (0.98 V vs. SCE). As-formed PDHN films showed good redox activity and stability, together with interesting electrochromic property from brown (doped) to yellow-green (dedoped). Structural characterization, including FTIR, 1H NMR, and quantum chemistry calculations, indicated that the polymerization of DHN probably occurred at C4 and C8 positions. Moreover, thermal analysis revealed that PDHN displayed better thermal stability than that synthesized by chemical method. The fluorescence spectral studies, together with the electrical tests, showed that PDHN was a good blue light-emitter (fluorescence quantum yield higher than 0.1) with an electrical conductivity of as high as 0.46 S/cm. |
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Keywords: | Poly(1,5-dihydroxynaphthalene) Conducting polymers Boron trifluoride diethyl etherate Electrochemical polymerization Fluorescence properties |
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