Molecular Composites from Rigid-Rod Poly(<i>p</i>-phenylene)s with Oligo(oxyethylene) Side Chains as Novel Polymer Electrolytes

Lauter, Ulrich; Meyer, Wolfgang; Wegner, Gerhard

doi:10.1021/ma961098y

Cited by 184 publications

(204 citation statements)

References 29 publications

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“…The 2,5-O-ditosyl-1,4:3,6-dianhydro-Dsorbitol (a) was prepared in THF/aqueous NaOH two-phase system, according a previously described procedure [27]. The tosylated isosorbide was treated with methoxyphenol in sodium carbonate/DMF system; thereby, a selective endo-monoalkylated isosorbide derivative (b) was obtained.…”

Section: Results and Discussion 31 Synthesis And Characterizationmentioning

confidence: 99%

New poly(p-phenylenevinylene) derivatives containing isosorbide unit in the side-chain

Zrida¹,

Hriz²,

Jaballah³

et al. 2014

Express Polym. Lett.

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Abstract. New conjugated PPV derivatives containing the chiral isosorbide group (P1-3) have been synthesized via the Gilch reaction. The polymers are optically active, soluble in common organic solvents and show good film-forming abilities. High number-average molecular weights were determined by size exclusion chromatography (SEC) (16·10 3 -21·10 3 g·mol -1 ). The molecular structures of the polymers were confirmed by nuclear magnetic resonance (NMR) and Fourier transform infrared (FTIR) spectroscopies. Thermogravimetric analysis of the polymers showed good thermal stability up to 320°C. The optical properties of these !-conjugated materials were investigated by UV-vis absorption and photoluminescence (PL) spectroscopies. The polymers show a yellow fluorescence in dilute solution, and an orange emission is observed in thin films. The introduction of the polar isosorbide groups improved the PL intensity, and quantum yields between 50 and 73% were obtained. The HOMO-LUMO energy levels were estimated by cyclic voltammetry, and the electrochemical gaps were 1.81, 1.83 and 2.48 eV for P1, P2 and P3, respectively. Single-layer diode devices were fabricated and show relatively low turn-on voltages between 3.1 and 3.4 V. Vol.8, No.10 (2014) 709-722 Available online at www.expresspolymlett.com DOI: 10.3144/expresspolymlett.2014.74 * Corresponding author, e-mail: mustapha.majdoub@fsm.rnu.tn © BME-PT insoluble in common organic solvents. This intractability has been addressed by chemically attaching aliphatic side-chains to the polymer backbone [19]. Hence, many PPV-type architectures are processed in a derivative form. The effects of the side-group structure on the opto-electronic properties have been extensively investigated [20]. However, most studies have involved nonpolar sidechains, and the effect of relatively polar side-groups was rarely reported (e.g PPV derivative containing ethylene oxide-type side chains) [12]. Here, we report the first PPV derivatives containing the polar and chiral isosorbide groups. In fact, the incorporation of chiral groups in polypyrroles and polythiophenes was reported. These groups confer original physico-chemical properties to the polymer [21][22][23]. Therefore, these optically active polymers were used to prepare chiral electrodes for asymmetric electrosynthesis, polarization-sensitive electro-optical devices, polarized photo-and electroluminescent devices and enantioselective sensors [24]. Herein, we present the synthesis and structural characterizations of the isosorbide-containing PPVs; the thermal, thin film surface, optical and electrochemical properties were investigated. Keywords: polymer synthesis, optically active polymers, semi-conducting polymers, isosorbide, photoluminescence eXPRESS Polymer Letters Experimental 2.1. Materials and measurementsThe poly (2-hexyloxy-5-methoxy-p-phenylenevinylene) (MH-PPV) was synthesized by using Gilch condensation. Detailed synthesis procedure can be found elsewhere [20].

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Section: Results and Discussion 31 Synthesis And Characterizationmentioning

confidence: 99%

New poly(p-phenylenevinylene) derivatives containing isosorbide unit in the side-chain

Zrida¹,

Hriz²,

Jaballah³

et al. 2014

Express Polym. Lett.

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“…This compound was prepared according to the literature. 20 Triethylene glycol (157 g, 1.00 mol) was stirred under nitrogen at 100 o C while sodium (6.90 g, 1.20 mol) in small portions was carefully added. After all the sodium reacted, the flask content was cooled to 50 o C and then α-(p-toluenesulfonyl)-ω-methoxytris(oxyethylene) (80.0 g, 0.25 mol) was added dropwise over 1 h. A white precipitate of sodium tosylate appeared after a few minutes.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, Self-assembly, and Catalytic Activity of 1H-Imidazole Amphiphiles

Park¹,

Kim²,

Seo³

et al. 2011

Bulletin of the Korean Chemical Society

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We prepared polycatenar 1H-imidazole amphiphiles having a structure in which a 1H-imidazole head was connected through a benzene ring to a pheny group having two or three oligo(ethylene glycol) chains and studied their supramolecular assembly by fluorescence spectroscopy, transmission electron microscopy (TEM) and atomic force microscopy (AFM). When the aqueous solutions of the amphiphiles (5 × 10 −5 M ~ 10 −3 M) were deposited onto a carbon-coated copper grid and dried, twisted structures with diameters of ~200-300 nm were imaged by TEM and AFM. We presume that the structures comprised a chain of the amphiphile dimers formed via successive hydrogen bonding between the 1H of the imidazole group and 3N of the neighboring one. In a solution of pH 4, entangled fibers with diameters of several nanometers were observed by TEM. In a pH 10 solution, film-like aggregates formed exclusively. The 1H-imidazole amphiphiles hydrolyzed tetraethoxysilane to induce gelation to form fibrous and spherical silica structures at neutral pH in aqueous solutions. No silica was formed when imidazole was used instead of the amphiphiles, suggesting that the selfassembled aggregates of the amphiphiles were responsible for the gelation.

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“…By using a statistical copolymer PPP(EO) x/y involving two different side-chain lengths (x and y) of oligo(ethylene oxide) side-chains, self-assembled materials have been introduced where the tendency for the side-chain crystallization is suppressed. Li + conduction is achieved by adding LiTFSi [266]. For longer side-chains, consisting of e.g.…”

Section: Self-assembled Ionically Conducting Polymersmentioning

confidence: 99%

“…Several types of hairy rods have been prepared (Fig. 3.16) [262,[264][265][266][274][275][276][277]. The polymers self-assemble to cylindrical or lamellar phases depending on the type and length of the alkyl chains [264,266].…”

Section: Self-assembly Of Conjugated Polymersmentioning

confidence: 99%