Synthesis of new Tetrazole based-semiconducting polymers for optoelectronic application: Study of the effect of anthracene group on photophysical properties

Gharbi, Samar; Zrida, Habiba; Hriz, Khaled; Chemek, Mourad; Wazzan, Nuha; Majdoub, Mustapha

doi:10.1016/j.molstruc.2021.131760

Cited by 7 publications

(9 citation statements)

References 71 publications

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“…were significantly red shifted and broadened, in comparison with those in dilute solutions. As mentioned in thin film absorption study, this behavior is ascribed to the π‐π interaction of the excited conjugated systems and excimer formation in the solid state [37,43] …”

Section: Resultsmentioning

confidence: 71%

“…Hence, the substitution of CN groups with the polar tetrazole heterocycles greatly improved the thermal stability of the macromolecule. Tetrazole groups are in fact known for their rigidity and relatively high polarity that causes important van der Waals interactions leading therefore to an improvement of the thermal stability of the tetrazole‐containing polymer [43] …”

Section: Resultsmentioning

confidence: 99%

“…Tetrazole groups are in fact known for their rigidity and ChemistrySelect relatively high polarity that causes important van der Waals interactions leading therefore to an improvement of the thermal stability of the tetrazole-containing polymer. [43]…”

Section: Thermal Propertiesmentioning

confidence: 99%

“…As mentioned in thin film absorption study, this behavior is ascribed to the π-π interaction of the excited conjugated systems and excimer formation in the solid state. [37,43]…”

Section: Chemistryselectmentioning

confidence: 99%

“…Our choice of anthracene as a building unit was motivated by its excellent quantum yield in luminescence, high thermal stability and good electron carrier which explain its widespread use in the synthesis of strongly photoluminescent conjugated polymers [29,30] and small molecules [31] . 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] .…”

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: 71%

Section: Resultsmentioning

confidence: 99%

Section: Thermal Propertiesmentioning

confidence: 99%

“…As mentioned in thin film absorption study, this behavior is ascribed to the π-π interaction of the excited conjugated systems and excimer formation in the solid state. [37,43]…”

Section: Chemistryselectmentioning

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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An eco‐friendly synthesis of 5‐aminotetrazoles using trichloroisocyanuric acid as desulfurization agent of thioureas

Moraes

Silva

Mattos

2023

Journal of Heterocyclic Chem

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A novel procedure for the preparation of various 5‐aminotetrazoles derivatives was achieved using trichloroisocyanuric acid as a desulfurizing agent of thioureas and trimethylsilyl azide in ethyl acetate at room temperature. This methodology provided substituted 5‐aminotetrazoles through a more sustainable reaction using an affordable, safe, stable, and easily handled N‐halo reagent, a safer azide source, and an environmentally friendly solvent.

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Anthracene and β‐Cyclodextrin Based Supramolecular Semi‐Conducting Thin Film: Effect of the Encapsulation on the Optical and Electrical Properties

et al. 2022

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In this study, we describe the synthesis of a host-guest supramolecule (TDPAnβ-CD) formed from an anthracene-based conjugated molecule (TDPAn, guest) encapsulated in cyclodextrin (β-CD, host) under microwave irradiation. The obtaining of the desired rotaxane was confirmed by different spectroscopic and thermal analyzes. A comparative study between the physicochemical and electrical properties of the free molecule (TDPAn) and those of the rotaxane (TDPAnβ-CD) was conducted. Thermal analyzes show an amorphous morphology and good thermal stability for the rotaxane. The surface morphology of the synthesized materials was studied using atomic force microscopy and contact angle measurement. The supramolecular film exhibits a smooth and homogeneous surface with a relatively low surface roughness compared to that of the free model. The absorption and photoluminescence spectra of the rotaxane thin film are blue-shifted in comparison with TDPAn, due to a steric hindrance effect of the β-CD. Hence, a blue intense photoluminescence was emitted from the rotaxane layer, compared to a violet-red emission in the case of non-encapsulated TDPAn. Higher electron affinity and ionization potential for the host-guest supramolecule were observed by cyclic voltammetry. The static study of ITO/ TDPAn/Al and ITO/TDPAnβ-CD/Al schottky single layer diodes showed typical behaviors with relatively low threshold voltages and higher charge carrier mobility was achieved for the rotaxane active layer.

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Synthesis of new Tetrazole based-semiconducting polymers for optoelectronic application: Study of the effect of anthracene group on photophysical properties

Cited by 7 publications

References 71 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

An eco‐friendly synthesis of 5‐aminotetrazoles using trichloroisocyanuric acid as desulfurization agent of thioureas

Anthracene and β‐Cyclodextrin Based Supramolecular Semi‐Conducting Thin Film: Effect of the Encapsulation on the Optical and Electrical Properties

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