Polymerization Of 2-ethynylpyridine Research Articles

The non-catalyst polymerization of 2-ethynylpyridine using (iodomethyl)trimethylsilane

The non-catalyst polymerization of 2-ethynylpyridine using (iodomethyl)trimethylsilane

Electro-optical and electrochemical properties of poly[2-ethynyl-N-(α-isobutyryl)pyridinium bromide

In the present study, we synthesized a new conjugated polyelectrolyte with the N-(α-isobutyryl)pyridinium bromide as substituents via the spontaneous, catalyst-free polymerization of 2-ethynylpyridine using α-bromoisobutyryl bromide. The polymerization proceeded well to give the resulting poly[2-ethynyl-N-(α-isobutyryl)pyridium bromide] in high yield. The polymer structure was characterized by means of such instrumental methods as IR, NMR, and UV-visible spectroscopies to have the conjugated backbone system with the N-(α-isobutyryl)pyridinium bromides. Absorption spectrum of polymer showed the maximum peaks of 334 and 411 nm. The electrochemical property of polymer was measured and discussed. Based on cyclic voltammetry data, this polymer had the HOMO value of 5.25 eV.

A polyelectrolytic polyacetylene for quasi-solid state dye-sensitized solar cell applications

A new polyelectrolytic polyacetylene, poly(2-ethynyl-N-iodopyridinium triiodide), was applied for DSSCs. Poly(2-ethynyl-N-iodopyridinium triiodide) was prepared by the non-catalyst polymerization of 2-ethynylpyridine using iodine without any additional initiator or catalyst in high yields. The photoluminescence peak was observed at 534 nm corresponding to a photon energy of 2.32 eV. Quasi-solid-state DSSCs with a SnO2:F/TiO2/D719 dye/solid-state electrolyte/Pt device was fabricated with the poly(2-ethynyl-N-iodopyridinium triiodide) electrolyte, which shows the power conversion efficiency (PCE) of 5.79%.

Synthesis and Characterization of Poly[N-(3-butynyl)-2-ethynylpyridinium bromide

A new conjugated polyelectrolyte with the N-(3-butynyl)pyridinium bromide was synthesized via the non-catalyst polymerization of 2-ethynylpyridine by using 4-bromo-1-butyne. The polymerization proceeded well to give the resulting poly[N-(3-butynyl)-2-ethynylpyridium bromide] in 75% yield. The chemical structure of poly[N-(3-butynyl)-2-ethynylpyridium bromide] was characterized by such instrumental methods as IR, NMR, and UV-visible spectroscopies to have the conjugated backbone system with the designed substituents. The electro-optical and electrochemical properties of polymer were measured and discussed. Comparing absorption spectrum and cyclic voltammetry data, this polymer had the HOMO and LUMO values of 5.33 and 3.35 eV, which means the band gap of 1.98 eV.

Synthesis and characterization of a polyacetylene electrolyte via the non-catalyst polymerization of 2-ethynylpyridine using 3-butynyl-p-toluenesulfonate

Synthesis and characterization of a polyacetylene electrolyte via the non-catalyst polymerization of 2-ethynylpyridine using 3-butynyl-p-toluenesulfonate

An ionic conjugated polymer from the non-catalyst polymerization of 2-ethynylpyridine using perfluorohexyl iodide

A new ionic conjugated polymer, poly(2-ethynyl-N-perfluorohexylpyridinium iodide) (PEPFHPI), was synthesized via the non-catalyst polymerization of 2-ethynylpyridine using perfluorohexyl iodide. The polymerization proceeded homogeneously to provide a moderate yield of polymer. The molecular structure of PEPFHPI was identified by such instrumental methods as IR, NMR, and UV-visible spectroscopies to have a conjugated polymer backbone system with N-perfluorohexylpyridinium iodide as substituents. The electro-optical and electrochemical properties of polymer were measured and discussed. Comparing absorption spectrum and cyclic voltammetry data, this polymer had the HOMO and LUMO values of 4.81 and 2.68 eV, which means the band gap of 2.13 eV.

An ionic polyacetylene derivative from the non-catalyst polymerization of 2-ethynylpyridine using 2-(bromomethyl)benzyl alcohol

ABSTRACTThe catalyst-free polymerization of 2-ethynylpyridine using 2-(bromomethyl)benzyl alcohol proceeded well to give a high yield of polymer (91%). The structural analysis of resulting polymer indicated that the resulting conjugated polymer have the (N-2-hydroxymethylbenzyl)pyridinium bromide as substituents. The absorption spectrum exhibited the maximum peak of 457 nm and the band gap was 2.15 eV. Overall redox current shape and values were very stable in the range of −1.5 V to 1.5 V under up to 50 cycles. Oxidation was started at 0.388 V. HOMO and LUMO levels were 5.14 and 2.99 eV, respectively.

Synthesis, optical and electrochemical properties of poly(N-bromo-2-ethynylpyridinium bromide)

ABSTRACTPoly(N-bromo-2-ethynylpyridinium bromide) was synthesized via the catalyst-free polymerization of 2-ethynylpyridine using bromine in high yield. The activated triple bonds of N-bromo-2-ethynylpyridinium bromide formed at the initial quaternization reaction are susceptible to linear polymerization, followed by an identical propagation step that contains the produced macroanion and quaternized N-bromo-2-ethynylpyridinium bromide species. The chemical structure of polymer was characterized by various instrumental methods to have the conjugated polymer backbone system bearing the designed N-bromo-2-pyridinium bromide substituents. The optical and electrochemical properties of polymer were studied. The UV-visible spectrum of polymer showed a characteristic absorption peak in the visible region (up to 800 nm). The photoluminescence emission spectrum of polymer shows two distinct peaks at 407 and 516 nm. The cyclic voltammetry of polymer exhibited irreversible electrochemical behavior between the oxidation and reduction peaks.

An ionic polyacetylene derivative with the N-[(triethylene glycol)methyl ether]pyridinium tosylate

ABSTRACTThe non-catalyst polymerization of 2-ethynylpyridine using tri(ethylene glycol)methyl ether tosylate yielded an ionic polyacetylene with the N-[(triethylene glycol)methyl ether]pyridinium tosylate substituents. The polymerization proceeded well in homogeneous manner to give the resulting poly{2-ethynyl-N[(triethylene glycol)methyl ether]pyridinium tosylate} in moderate yield. The polymer was completely soluble in such organic solvents as methanol, DMF, DMSO, NMP including water. The chemical structure of the resulting polymer was characterized by such instrumental methods as IR, NMR, and UV-visible spectroscopies to have the conjugated backbone system with the N-[(triethylene glycol)methyl ether]pyridinium tosylate. The absorption spectrum starts around 600 nm, which is due to the π→ π* interband transition of conjugated polymer system. HOMO and LUMO level were 5.46 and 3.39 eV. The electrochemical properties of polymer was also measured. This polymer exhibited initial onset voltage of 0.73 V for oxidation and stable redox property up to 50 cycles.

Poly(N-bromo-2-ethynylpyridinium bromide) for quasi-solid state dye-sensitized solar cell applications

ABSTRACTA new conjugated ionic polymer, poly(N-bromo-2-ethynylpyridinium bromide) (PBEPB) was applied for a quasi-solid-state dye-sensitized solar cells (DSSCs) and compared the device performance with poly(N-bromo-2-ethynylpyridinium iodide) (PBEPI) as reference cell. The polymer was prepared by the spontaneous polymerization of 2-ethynylpyridine using bromine. The PBEPB was completely soluble in such organic solvents as DMF, DMSO and NMP etc. The photoluminescence peaks of PBEPB was observed at 407 nm and 516 nm, which corresponds to the photon energy of 3.15 eV and 2.41 eV, respectively. Quasi-solid-state DSSCs with a SnO2:F/TiO2/D719 dye/solid-state electrolyte/Pt device was fabricated with an ionic conjugated polymer with pyridinium substituents, which shows the power conversion efficiency (PCE) of 5.95%.

Photovoltaic properties of polyacetylene derivative for quasi-solid state dye-sensitized solar cell applications

ABSTRACTIn this study, we introduce polyacetylene-based polyelectrolyte for quasi-solid-state dye sensitized solar cells (DSSCs) applications. A conjugated polyelectrolyte was prepared via the phosphorus oxychloride-activated polymerization of 2-ethynylpyridine. Poly[2-ethynyl-N-(dichlorophosphino)pyridinium chloride] was applied for DSSCs. The photoluminescence (PL) spectrum of polymer solution showed the two maximum peaks of 471 nm and 489 nm corresponding to the photon energy of 2.64 eV and 2.54 eV, respectively. Quasi-solid-state DSSCs with a SnO2:F/TiO2/D719 dye/solid-state electrolyte/Pt device was fabricated with Poly[2-ethynyl-N-(dichlorophosphino)pyridinium chloride], which shows the maximum power conversion efficiency (PCE) of 5.70%.

Synthesis of an ionic polyacetylene derivative via phosphorus oxychloride-activated polymerization of 2-ethynylpyridine

ABSTRACTA new ionic polyacetylene was synthesized via the non-catalyst polymerization of 2-ethynylpyridine using phosphorus oxychloride. The polymerization proceeded well in homogeneous manner to give a moderate yield of polymer (74%). The resulting polymer was completely soluble in polar organic solvents including water. The photoluminescence spectrum showed the two maximum peaks of 471 nm and 489 nm corresponding to the photon energy of 2.64 eV and 2.54 eV, respectively. The oxidation and reduction onset potentials of polymer were observed at 970 and −130 mV, respectively.

Preparation and characterization of polyacetylene electrolyte via the non-catalyst polymerization of 2-ethynylpyridine

Preparation and characterization of polyacetylene electrolyte via the non-catalyst polymerization of 2-ethynylpyridine

An ionic polyacetylene from the non-catalyst polymerization of 2-ethynylpyridine using 1,6-dibromohexane: Synthesis and characterization

ABSTRACTAn ionic polyacetylene was prepared via the non-catalyst polymerization of 2-ethynylpyridine using 1,6-dibromohexane. The polymerization proceeded in homogeneous manner to give a high yield of polymer (88%). The polymer structure was characterized by such instrumental methods as IR, NMR, and UV-visible spectroscopies to have the conjugated polymer backbone with the designed bromohexylpyridinium substituents. The absorption spectrum exhibits several absorption peaks such as 289, 330, 387, and 489 nm and band gap was 2.44 eV. The photoluminescence spectrum of polymer showed the maximum peak at 550 nm. Overall redox current shape and values were very stable in the range of −1.5 V to 1.5 V under up to 50 cylcles. Oxidation and reduction were started at 0.35 and −0.6 V.

A conjugated polymer electrolyte for quasi-solid state dye-sensitized solar cell applications

ABSTRACTA new conjugated ionic polymer was applied for DSSCs. Poly(2-ethynyl-N-methylpyridinium iodide) (PEMPI) was prepared by the non-catalyst polymerization of 2-ethynylpyridine using iodomethane without any additional initiator or catalyst. The polymerization proceeded homogeneously to give a high yield of polymer (87%). The photoluminescence peak was observed at 568 nm corresponding to a photon energy of 2.19 eV. Quasi-solid-state DSSCs with a SnO2:F/TiO2/D719 dye/solid-state electrolyte/Pt device was fabricated with PEMPI, which shows the maximum power conversion efficiency (PCE) of 6.01%.

Synthesis of Poly(2-Ethynylpyridinium Trifluoroacetate) by Spontaneous Polymerization

Poly (2-ethynylpyridinium trifluoroacetate) (P2EPF) was synthesized by the spontaneous polymerization of 2-ethynylpyridine (2-EP) and trifluoroacetic acid (TFA). TFA, as a strong acid for sufficient activation of the acetylenic triple bond, was used in the spontaneous polymerization of 2-EP producing conjugated and ionic polyacetylenes. P2EPF was soluble in polar organic solvents due to inherent characteristics of ionic polymers. The chemical structure and composition of P2EPF were characterized by 1H-NMR, 13C-NMR, FT-IR, and UV-Vis spectrometer. The fluorescence spectra of P2EPF suggested that P2EPF were successfully synthesized as potential conducting materials.

Synthesis and Characterization of Poly[N-(4-nitrobenzenesulfonyl)-2-ethynylpyridinium chloride

An ionic polyacetylene with 4-nitrobenzenesulfonyl substituents was easily prepared via the non-catalyst polymerization of 2-ethynylpyridine using 4-nitrobenzenesulfonyl chloride. The polymerization proceeded in homogeneous manner to give a moderate yield of polymer (65 %). The polymer structure was characterized by such instrumental methods as IR, NMR, and UV-visible spectroscopies to have the conjugated backbone system with the designed N-(4-nitrobenzenesulfonyl)pyridinium chloride. The photoluminescence peak was observed at 584 nm corresponding to a photon energy of 2.12 eV although it is weak due to nitro group. Based on absorption spectrum, band gap was 2.16 eV. The cyclic voltammograms of polymer exhibited the electrochemically stable window at the −1.8 ∼ 1.50 V region. Oxidation and reduction were started at 0.43 and −0.9 V and had stable electrochemical property up to 30 cycles.

Synthesis of an Ionic Polyacetylene Derivative via the Non-catalyst Polymerization of 2-Ethynylpyridine Using 4-(Bromomethyl)-7-methoxycoumarin

A new ionic polyacetylene with coumarin moieties was synthesized via the non-catalyst polymerization of 2-ethynylpyridine using 4-bromomethyl-7-methoxycoumarin in high yield. The polymerization proceeded well in homogeneous manner to give 75% of yield without any additional catalyst or initiator. The polymer structure was identified by such various instrumental methods as NMR, IR, and UV-visible spectroscopies to have a conjugated backbone with the designed coumarin groups. The photoluminescence peak was observed at 512 nm corresponding to a photon energy of 2.42 eV. The cyclovoltamograms of polymer exhibited the electrochemically stable window at the −1.8 ∼ 1.50 V region. Oxidation and reduction were started at 0.58 and −0.8 V and had stable electrochemical property up to 30 cycles.

Synthesis and Properties of an Ionic Conjugated Polymer via the Uncatalyzed Polymerization of 2-Ethynylpyridine Using Bromocholine Bromide.

A new ionic polyacetylene was synthesized via the uncatalyzed polymerization of 2-ethynylpyridine using bromocholine bromide in high yield. The activated acetylenic triple bond of N-bromocholine-2-ethynylpyridinium bromide, formed at first quaternarization process, was found to be susceptible to linear polymerization. The polymer structure was characterized by various instrumental methods to have the polyacetylene backbone structure with the designed substituent. The inherent viscosities of the resulting polymers were in the range of 0.10-0.15 dL/g and X-ray diffraction analysis data indicated that this polymer is mostly amorphous. The electro-optical and electrochemical properties were measured and discussed. The polymer exhibited the irreversible electrochemical behaviors between the doping and undoping peaks.

Synthesis and properties of an ionic conducting material: in-situ preparation of poly(2-ethynyl-N-iodopyridinium iodide) and its electro-optical and electrochemical properties.

Poly(2-ethynyl-N-iodopyridinium iodide) [PEIPI] was easily prepared via in-situ uncatalyzed polymerization of 2-ethynylpyridine by using iodine. The activated acetylenic bond of 2-ethynyl-N-iodopyridinium iodide formed at the initial reaction time was assumed to be susceptible to linear polymerization, followed by an identical propagation step that contains the produced macroanion and quaternized monomeric species. The polymer structure was characterized by various instrumental methods to have the conjugated polymer backbone system bearing the designed substituents. The electro-optical and electrochemical properties of polymer were studied. The UV-visible spectrum of PEIPI showed a characteristic absorption peak in the visible region up to 800 nm. The PL emission spectrum of PEIPI shows two peaks at 515 and 550 nm. The cyclic voltammetry of PEIPI exhibited irreversible electrochemical behavior between the oxidation and reduction peaks.