Toward Network Electrochromic Film: Secondary Polymerization of Methacrylate Functionalized Thiophene
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A novel methacrylate modified 2-(3-thienyl)ethyl methacrylate (TE-MA) was synthesized, and free radical polymerized and electrochemical polymerized to obtain the precursor polymer polymethacrylate (PMA) functionalized with thiophene (TE-PMA) and PMA modified polythiophene (PTE-PMA), respectively. Structure characterization and properties of PTE-PMA, including FT-IR, morphology, electrochemical, and electrochromic properties, were systematically investigated. In addition, PTE-PMA exhibited obvious color changes from gray to purple and good electrochromic properties, including satisfactory coloration efficiency (128 cm2 C-1 at 400 nm; 115 cm2 C-1 at 900 nm) and fast response time.Keywords:
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Electrochromism is the phenomenon displayed by the materials of reversibly changing color when the electric potential is applied. We have developed new type of electrochromic materials having the polyrotaxane structure, in which the semiconductive polymer (polythiophene) is wrapped by many macrocycles [tetracationic cyclophane, cyclobis (paraquat-p-phenylene)]. Compared with the reference polythiophene without macrocycle, the polythiophene polyrotaxane thin film has more homogeneous surface and brighter color, and shows larger color contrast and faster response in the electrochromic process. These results arise from two factors based on the polyrotaxane structure. One is the weakened molecular interactions between the polythiophene chains by the macrocycles. The other is the counter anions of the tetracationic cyclophane which provides the pathway for the migration of the counter anion between the electrolyte solution and the film in redox process. These results indicate that the encapsulation of the semiconductive polymers by the macrocycles is one of the powerful methods to enhance the functionality of the materials.
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Summary form only given. The experimental study of oligothiophenes offers the possibility to investigate model compounds for polythiophene with a defined chain length. Oligorners are free of mislinkages and defects which are introduced into polythiophene by the chemical or electrochemical polymerization process. Upon oxidation of unsubstituted oligothiophenes - especially short ones - there always remains the possibility, of polymerization at the terminal thiophene units. To prevent further polymerization during oxidation, several research groups investigated oligothiophenes substituted at the terminal thiophene units: methyl-substitutents at the terminal /spl alpha/-positions as well as cyclohexene units condensed to the terminal thiophene rings. We studied thiophene oligomers with cyclohexene units at the terminal thiophene units (end-capped oligothiophenes) in their neutral state with FTIR- and FT-Raman spectroscopy. Furthermore we present results on the oxidation of end-capped oligothiophenes with iodine vapor studied with in situ FTIR-spectroscopy using the ATR technique.
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Three kinds of substituted polythiophenes,3-hexyl polythiophene(P3HT),3,4-dipentyl polythiophene(P34PT) and 3-octoxyl polythiophene(P3OOT) were synthesized.The()~1H-NMR spectra,UV-Vis absorption spectra and the fluorescence spectra of each polymer are also reported.Theoretical studies on the thiophene with no substituent,3-ethyl thiophene,3,4-diethyl thiophene and 3-ethoxyl thiophene dimers were performed with density functional theory(DFT) using Gaussian03 software package.The influences of the substituents on the electrical properties and conformations of polythiophenes are studied and the theoretical results are compared with the experimental results.The energy gaps of polymers turn narrower with the increase of polymerization degrees.The(energy) gaps and repeating unit lengths of nonsubstituted thiophene,3-ethyl thiophene,3,4-diethyl thiophene and 3-ethoxyl thiophene(dimers) are 4.216 eV,0.392 7 nm,4.733 eV,0.393 9 nm,3.890 eV,0.390 8 nm,5.168 eV,0.392 5 nm,respectively.
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This paper reports on the preparation of a conducting polythiophene polymer covalently bonded to a thiophene-terminated boron-doped diamond (BDD) electrode. The thiophene-terminated BDD surface was prepared using "click" chemistry in a stepwise process. Azide termination on BDD was obtained via esterification reaction of photochemically oxidized diamond surfaces with 4-azidobenzoic acid in the presence of N,N-dicyclohexylcarbodiimide at room temperature. The applicability of azide−alkyne [3 + 2] cycloaddition reaction was successfully demonstrated using ethynyl thiophene. Electropolymerization was conducted on the thiophene-terminated BDD surface in the presence of thiophene monomer to form a polythiophene film covalently grafted on the BDD interface. The resulting surfaces were characterized using cyclic voltammetry, X-ray photoelectron spectroscopy, scanning electron microscopy, and contact angle measurements.
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Polythiophene
Electrochromic devices
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Conducting polymer has been a relatively independent scientific field due to the development of research on it. In this paper, the development of research on conducting polymer was introduced, especially polyacetylene, polyaniline, polypyrrole, polythiophene. At the same time, the main aspects to be improved were predicted.
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Here the authors designed and synthesized three branched thiophene polymers with different effective conjugation lengths of thiophene groups, pTPBT, pTPTT, and pTPQT, mainly based on bithiophene, trithiophene, and quadruple thiophene. The electrochemical curves and theoretical calculation results reflect that the oxidation potential of polymers decreased gradually as the conjugation lengths of thiophene groups increased, which is favorable for the appearance of electrochromism. Electrochromic properties demonstrate that pTBTT displays no electrochromism, pTPTT exhibits an unstable one, while pTPQT shows an obvious stable electrochromism between yellow‐orange and blue‐violet colors. These results indicate that thiophene polymers with effective electrochromism should be the smallest conjugation length of quadruple thiophene at least. © 2019 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 2340–2348
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Polythiophene thin films are prepared from several thiophene derivatives, such as 2, 5-dichlorothiophene(DCT), 2, 5-dibromothiophene(DBT) and 2, 5-diiodothiophene(DIT) by UV laser-assisted deposition (UV-LAD) with 193 (ArF), 248 (KrF) and 308nm (XeCl) beams. Each film prepared by UV-LAD possesses highly oriented fibrous structure called laser induced periodic structure (LIPS). Electric conductivities of some films have increased from less than 10-7S cm-1 up to 10-3S cm-1 by doping with iodine after UV-LAD. FT-IR, ESCA and UV-vis. spectra show that, although sulfur atoms are eliminated to some extent, polymerization basically occurs at 2(α)-5(α′) positions of the thiophene derivatives by elimination of halogen atoms. For the film prepared by UV-LAD of DIT at 308nm, the average conjugation length is estimated to be corresponding to that of thiophene oligomers consisting of 4±1 thiophene units.
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