Synthesis and characterization of new anthracene‐based semiconducting polyethers

Hriz, Khaled; Jaballah, Nejmeddine; Chemli, Mejed; Fave, Jean‐Louis; Majdoub, Mustapha

doi:10.1002/app.32659

Cited by 22 publications

(12 citation statements)

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“…The obtained derivative (c) was then O-alkylated with different aliphatic chain: ethyl, hexyl and dodecyl. The aromatic group of the isosorbide diethers (d1-3) was chloromethylated using the HCl/paraformaldehyde/acetic acid system [30] to obtain the corresponding isosorbide-containing monomers (e1-3). The PPV polymers (P1-3) were synthesized via the Gilch polycondensation of these aromatic dichloromethyl derivatives in DMF and using tert-butoxide as the basic condensing agent [20] (Figure 1).…”

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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“…Because of the lack of interaction with polymeric materials, the anthracene group has been selected by various research teams to be introduced into polymers 11. Anthracene‐containing polymers have been used in the fabrication of optoelectronic devices,12–14 photoluminescent films,15, 16 photoresists,17, 18 chemiluminescent fluorophores,19–21 and so forth.…”

Section: Introductionmentioning

confidence: 99%

Well‐defined diblock copolymers possessing fluorescent and metal chelating functionalities as novel macromolecular sensors for amines and metal ions

Demetriou

Krasia‐Christoforou

2011

J. Polym. Sci. A Polym. Chem.

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The amino‐ and metal‐ion sensing capability of a novel type of well‐defined block copolymers based on 9‐anthrylmethyl methacrylate (AnMMA; hydrophobic, fluorescent) and 2‐(acetoacetoxy)ethyl methacrylate (AEMA; hydrophobic, metal chelating) has been investigated in organic media. AEMAx‐b‐AnMMAy diblock copolymers were prepared for the first time using reversible addition‐fragmentation chain transfer (RAFT) polymerization. All polymers were characterized in terms of molecular weights, polydispersity indices and compositions by size exclusion chromatography and 1H NMR spectroscopy, respectively. The glass transition (Tg) temperatures of the AEMAx and AnMMAx homopolymers and the AEMAx‐b‐AnMMAy diblock copolymers were determined using differential scanning calorimetry. These systems were evaluated toward their ability to act as effective dual chemosensors (i.e., amino‐ and metal‐ion sensors) in an organic solvent (chloroform). More precisely, the fluorescence intensity of both the AnMMAx homopolymers and the AnMMAx‐b‐AEMAy diblock copolymers in solution exhibited a significant decrease in the presence of triethylamine. Moreover, the presence of iron (III) cations were also found to significantly affect the fluorescence signal of the anthracene moieties when those were combined in a block copolymer structure with the AEMA units, due to complex formation occurring between the β‐ketoester groups of the AEMAx segment and the cations. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012

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“…A new aromatic dialdehyde (M 1 ), used as monomer, was prepared from 4,4 0 -thiodiphenol (TDP) according to a four steps synthetic route as showed in Scheme 1. The first step consists on a direct chloromethylation of the benzene ring of the corresponding ethylated ether (a) in an HCl/paraformaldehyde/acetic acid system following a conventional described procedure [29]. Then, the diacetate derivative (c) was obtained by nucleophilic substitution of chloride by acetate group.…”

Section: Synthesis and Structural Characterizationmentioning

confidence: 99%

“…The last step is an oxidation of the primary alcohols in (d) by using the pyridinium chlorochromate (PCC). The 9,10-bis(chloromethyl)anthracene (AnCl) was synthesized by direct chloromethylation of the anthracene using the HCl/paraformaldehyde/acetic acid system, following our previously reported procedure [29]. The correspondent triphenylphosphonium salts (M 2 ) was then obtained by acetone reflux of the AnCl in presence of triphenylphosphine.…”

Section: Synthesis and Structural Characterizationmentioning

confidence: 99%

New anthracene-based semi-conducting polymer analogue of poly(phenylene sulfide): Synthesis and photophysical properties

et al. 2015

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Synthesis and characterization of new anthracene‐based semiconducting polyethers

Cited by 22 publications

References 42 publications

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

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

Well‐defined diblock copolymers possessing fluorescent and metal chelating functionalities as novel macromolecular sensors for amines and metal ions

New anthracene-based semi-conducting polymer analogue of poly(phenylene sulfide): Synthesis and photophysical properties

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