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

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

doi:10.1016/j.optmat.2015.04.055

Cited by 9 publications

(8 citation statements)

References 42 publications

(51 reference statements)

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“…The monomer AnCN was prepared by cyanation of dichloromethyl anthracene (AnCl) with KCN in DMF at room temperature. The synthesis of M 1 monomer was reported in our previous work [36] . It was carried out in five steps: an alkylation followed by a reaction of chloromethylation, then an acetylation and saponification and finally an oxidation of the primary alcohols in the presence of PCC which leads to the preparation of aldehyde functions.…”

Section: Resultsmentioning

confidence: 99%

“…The main interest of this part is to study the effect of nitrile and tetrazole groups on the electronic structure and photophysical properties of the synthesized organic materials and to compare them with our previously prepared anthracene-based analogue, poly(p-phenylene sulfide) (PAnS). [36] Figure 4 shows the normalized UV-Vis absorption spectra of PAnS, PAnSCN and PAnSCN-Tet in dilute chloroform solution (5.10 À 5 mol. L À 1 ).…”

Section: Optical Properties In Dilute Solutionmentioning

confidence: 99%

“…The monomers 9,10-dicyanomethylanthracene (AnCN) and 1,1'thiodi[3-(diformyl)-4-ethoxybenzene] (M 1 ) were synthesized according to our previously reported work. [36,37]…”

Section: Synthesis Of Monomersmentioning

confidence: 99%

“…These conjugated organic compounds showed their efficiency as active layer in Organic Light Emitting Diodes (OLEDs), [32] transistors, [33] photovoltaic cells [34] and above all anthracene derivatives are widely used as fluorophores for chemosensors owing to its photostability and chelation‐enhanced fluorescence (CHEF) characteristics [35] . As mentioned in previous studies, [36] the (PPS) is a high‐performance thermoplastic (HPTP) which has good thermal stabilityand a glass transition temperature of 85 °C as well as good oxidation resistance. Furthermore, when doped, PPS's electrical conductivity can reach values higher than 10 S.cm −1 .…”

Section: Introductionmentioning

confidence: 99%

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Effect of Cyano and Tetrazole Side Groups on the Photophysical and Chelating Properties of Anthracene‐Based Polymers

et al. 2023

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This paper covers the conception of new soluble and filmogene conjugated polymers (PAnSCN and PAnSCN‐Tet) for heavy metal sensing application. The prepared materials are based on the highly emissive anthracene chromophore and contain tetrazole and/or cyanide groups in their molecular chain backbones. The effect of the electron withdrawing groups on photophysical properties and the chelating abilities of the elaborated organic materials were investigated. The optical analysis shows that the CN groups reduced slightly the optical band‐gap of the polymer, however the steric hindrance of tetrazole units dominates their electronic effects leading to a blue‐shift of its absorption spectrum. Also, the electrochemical study reveals a considerable electronic affinity increase by 0.84 eV when passing from PAnSCN into PAnSCN‐Tet. DFT calculations has been employed to estimate the optimized macromolecular structure of both polymers and a notable change in geometry in terms of planarity was observed depending on the incorporated withdrawing group. The synthesized polymers were studied as optical sensors. The changes in the photoluminescence intensity were used to evaluate the binding affinity of the two materials to different metal ions. The obtained results showed considerable decrease in photoluminescence (quenching) responses with Mn2+ cations a short time after adding the cations to both polymer solutions with better sensitivity and selectivity in the case of the PAnSCN‐Tet.

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Section: Resultsmentioning

confidence: 99%

Section: Optical Properties In Dilute Solutionmentioning

confidence: 99%

“…The monomers 9,10-dicyanomethylanthracene (AnCN) and 1,1'thiodi[3-(diformyl)-4-ethoxybenzene] (M 1 ) were synthesized according to our previously reported work. [36,37]…”

Section: Synthesis Of Monomersmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Effect of Cyano and Tetrazole Side Groups on the Photophysical and Chelating Properties of Anthracene‐Based Polymers

et al. 2023

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“…because of their highly π-conjugated polymeric chains and metal like conductivity [1]- [4]. The optical properties of conducting polymers [5]- [7] are as important as electrical properties because they allow number of applications such as sensing [8]- [10], displays and other opto-electronic applications [11] [12]. Along with various advantages, these pristine conducting polymers have several drawbacks such as poor emission, processability and stability.…”

Section: Introductionmentioning

confidence: 99%

Highly Fluorescent Conducting Polymer Hybrid Materials Based on Polyaniline-Polyethylene Glycol-Arsenic Sulphide

Singh

Gupta

et al. 2016

IJOC

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Highly fluorescent binary and ternary hybrid materials based on polyaniline, polyethylene glycol (PEG) and arsenic sulphide have been prepared via oxidative chemical polymerization and characterized by FT-IR and powder X-ray diffraction techniques. Thermogravimetric analysis showed that all the materials are thermally stable up to 250˚C. The optical behaviour was investigated using UV-Vis. and fluorescence spectroscopy. Fluorescence spectra of polyaniline and its hybrids were found to be concentration dependent, and concentrations were optimized to achieve maximum intensity of emission. Aggregation caused quenching (ACQ) may be the possible reason for concentration dependent emission. Hybrids showed significantly enhanced fluorescence than polyaniline. The AC electrical conductivity was also measured and found to be better for hybrids than the polyaniline. In the PAni-PEG-As2S3 hybrid, the conductivity was found to be 9.57 × 10 −1 S/cm at 100 KHz. This valuable improvement in luminescent property and conducting behaviour may be useful in various optoelectronic and electronic applications.

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Preparation and Characterization of poly(Azomethines) Containing Ether and Methylene Bridges: Photophysical, Electrochemical, Conductivity and Thermal Properties

Kaya

Yilmaz

2016

J Fluoresc

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In this paper, a series of polyazomethines (PAZs) were prepared using dihydroxy substituted Schiff bases and 1,4-diiodobenzene. Also, different group effect such as methylene carbon and etheric oxygen bridges on photophysical, electrochemical, conductivity and thermal properties were clarified. The new polymeric materials structures were confirmed by means of H-NMR, FT-IR and UV-vis measurements. The molecular weight distributions of polymers were determined with gel permeation chromatography (GPC) measurements. Photophysical behaviors of polymers were explored by UV-vis absorption and fluorescence measurements. TGA-DTA and DSC techniques have been used for the thermal characterization of the PAZs. Thermal data and fluorescence measurements showed that etheric oxygen bridge containing polymers have a bit higher char and emission intensity than the methylene carbon bridge carrying polymers. According to TG analysis, T values of P-2MPDP, P-2-OPDP, P-4-MPDP and P-4-OPDP were found as 210, 250, 249 and 233 °C, respectively. The HOMO-LUMO energy levels, electrochemical (E' ) and optical (E ) band gaps were calculated from cyclic voltammetry (CV) and UV-vis measurements, respectively. The electrochemical (E ') band gaps values of P-2MPDP, P-2-OPDP, P-4-MPDP and P-4-OPDP were calculated as 2.68, 2.32, 2.34 and 2.07, respectively. Additionally, four-point probe technique was used to measure solid state electrical conductivities of both doped and undoped states of the PAZs.

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

Cited by 9 publications

References 42 publications

Effect of Cyano and Tetrazole Side Groups on the Photophysical and Chelating Properties of Anthracene‐Based Polymers

Effect of Cyano and Tetrazole Side Groups on the Photophysical and Chelating Properties of Anthracene‐Based Polymers

Highly Fluorescent Conducting Polymer Hybrid Materials Based on Polyaniline-Polyethylene Glycol-Arsenic Sulphide

Preparation and Characterization of poly(Azomethines) Containing Ether and Methylene Bridges: Photophysical, Electrochemical, Conductivity and Thermal Properties

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