New zinc phthalocyanine derivatives for nitrogen dioxide sensors: A theoretical optoelectronic investigation

Chaabéne, Marwa; Gassoumi, Bouzid; Mignon, Pierre; Chaâbane, Rafik Ben; Allouche, Abdul‐Rahman

doi:10.1016/j.jmgm.2019.01.008

Cited by 27 publications

(12 citation statements)

References 38 publications

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“…[ 49–51 ] This CT complex is presumably formed during the coordination of the NO 2 molecule at the zinc atom in ZnPc. [ 52–55 ] The transition of ZnPc to [ZnPc] +• in the complex with nitrogen dioxide leads to the quenching of the initial Q‐band absorption and the appearance of the so‐called “fingerprint” band in the region of ≈520 nm (see Figure S5, Supporting Information), associated with the single‐electron excitations from low‐lying doubly occupied orbitals 5 e g , 6 e g (HOMO– n ) toward the half‐empty 2 a 1u orbital (SOMO). [ 49 ] We also managed to observe the appearance of this band under the action of NO 2 on a bare monolayer of the ZnPc studied herein ( Figure a).…”

Section: Resultsmentioning

confidence: 99%

Resonant Plasmon‐Enhanced Absorption of Charge Transfer Complexes in a Metal–Organic Monolayer

Krichevsky

Tolbin

Dubinina

et al. 2021

Advanced Optical Materials

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Plasmonic enhancement of absorption in charge‐transfer (CT) complexes formed under NO2 gas adsorption onto 2D hybrid structure, based on the metal–organic monolayer and gold nanoparticles (AuNPs), is demonstrated. By using Langmuir–Blodgett deposition of low‐symmetry zinc phthalocyanine (ZnPc) molecules, the metal–organic monolayer is fabricated with greatly suppressed intermolecular aggregation. Oxidation of the monolayer through coordination of NO2 molecules with axial zinc ions of ZnPc molecules gives rise to the specific absorption band inherited to cation radical ZnPc+. The hybrid AuNPs–ZnPc structure is engineered to maximize exciton–plasmon interaction of CT complexes at the radical form of the metal–organic monolayer. Excellent spectral and spatial overlaps with plasmon resonance boost absorption of CT internal optical transition, so‐called “fingerprint” band, by a factor of six from 0.45% to 2.8% in total. The approach paves the way for efficient plasmonic control over photochemical reactions promoted by charge‐transfer complexes in metal–organic films. In particular, the plasmonic effect is harnessed to improve NO2 gas sensing properties; the experimental study shows a 15‐fold increase of the detection efficiency in the specific band of CT complexes under the gas exposure.

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Section: Resultsmentioning

confidence: 99%

Resonant Plasmon‐Enhanced Absorption of Charge Transfer Complexes in a Metal–Organic Monolayer

Krichevsky

Tolbin

Dubinina

et al. 2021

Advanced Optical Materials

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“…The precipitate was ltered off, washed with water to neutralize it, the product was dried in a vacuum oven at 80 ° C. MP: 153-156° C. Yield: 0.740 gr. The product is soluble in CHCl [1,3] dioxol-5-ylmethoxy) phenoxy) phthalocyaninato) zinc (II) (5) A mixture of 4- (2-(benzo[d] [1,3] dioxol-5-ylmethoxy) phenoxy) phthalonitrile 4 (0.050 g, 0.135 mmol) and ZnCl 2 (0.015 g) mixture was powdered in a quartz crucible and heated in a sealed glass tube for 5 min 210 ºC in the presence of DBU (2 drops). After reaching room temperature, the product was washed with hot and cold water, ethanol, methanol.…”

Section: Methodsmentioning

confidence: 99%

“…It is produced and used for fty tons of paint industry worldwide [1,2]. Besides, it is used in many elds such as catalyst [3], sensor [4,5], liquid crystal [6], optical data storage [7,8], solar cells [9]. Photodynamic therapy, which is one of the cancer treatment methods, is being researched as the subject of intensive research [10][11][12].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, DFT Calculations, Photophysical, Photochemical Properties of Peripherally Metallophthalocyanines Bearing (2-(Benzo[d] [1,3] Dioxol-5-Ylmethoxy) Phenoxy) Substituents

Solğun

Yıldıko

Ağırtaş

2021

Polycyclic Aromatic Compounds

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4- (2-(benzo[d] [1, 3] dioxol-5-ylmethoxy) phenoxy) phthalonitrile was rst prepared as a starting material.Then, this new phthalonitrile derivative was reacted with Zn and Co salts to obtain new phthalocyanine complexes. Phthalocyanine complexes were evaluated by uorescence emission, extinction, and absorption measurements. Aggregation studies show the compliance with the lambert-beer law in the concentration range studied for peripheral phthalocyanine compounds. The density functional theory (DFT) calculations of the metallophthalocyanines compounds were performed using B3LYP / 6-31G in Zn-Pc and B3LYP / LanL2DZ in Co-Pc to derive structural optimization, HOMO-LUMO energy parameters, and NLO properties. The calculated values of M-Pcs with different center atoms were obtained close to each other. Molecular electronic surface (MEP) maps of the studied compounds are mapped and discussed. The HOMO-LUMO energy gaps of our compounds studied are around 2.1 eV. The docking studies were performed with the phthalonitrile.

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“…Furthermore, we have obtained that B3LYP‐D3 gave the lowest gap energy and is the closest to the experimental results when compared to the other functional. Also, it was commonly used in literature where it provides an efficient and robust basis for III–V semiconductor computations …”

Section: Methodsmentioning

confidence: 99%

Theoretical and experimental investigations of complexation with BF₃.Et₂O effects on electronic structures, energies and photophysical properties of Anil and tetraphenyl (hydroxyl) imidazol

Chaabéne

Agren

Allouche

et al. 2019

Applied Organom Chemis

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The novel compounds (E)-2-(((4-hydroxyphenyl)imino)methyl)phenol, Tetraphenyl (hydroxyl) imidazole and their corresponding Boron difluoride complexes were synthesized and characterized by spectroscopic techniques.Density functional theory calculations at B3LYP-D3/6-311++G (d, p) level of theory were performed for the geometric parameters. The MEP surface studies were used to understand the behavior of molecules in terms of charge transfer and to determine how these molecules interact. We used the GIAO and the B3LYP-D3 with a 6-311++ G (d, p) basis set to simulate the ( 1 H-NMR and 19 F-NMR) and the IR spectra, respectively. The corresponding calculated results are in good agreement with the experimental data. The stability of the molecule arising from hyperconjugation interaction and charge delocalization were analyzed using NBO analysis. FMOs revealed the occurrence of charge transfer within the molecule. The complexation using BF 3 .Et 2 O was also found to have remarkable effects on the electrochemical properties of the studied molecules, where (b) and (d) present lower chemical stability, higher reactivity and higher polarizability than (a) and (c), respectively. Moreover, the energy gap of (a) and (c) decreased after complexation using BF 3 .Et 2 O, indicating the reliability of the electrochemical evaluation of LUMO and HOMO energy levels. These values are the factors explaining the possible charge transfer interaction within the molecule. The absorption and emission spectra of the model compound were also simulated and compared to experimental observations in the DMF solvent. The results of DFT calculations supported the structural and spectroscopic data and confirmed the structure modification of frontier molecular orbitals for BF 2 complexes as well as tunable potentials and energy levels.

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New zinc phthalocyanine derivatives for nitrogen dioxide sensors: A theoretical optoelectronic investigation

Cited by 27 publications

References 38 publications

Resonant Plasmon‐Enhanced Absorption of Charge Transfer Complexes in a Metal–Organic Monolayer

Resonant Plasmon‐Enhanced Absorption of Charge Transfer Complexes in a Metal–Organic Monolayer

Synthesis, DFT Calculations, Photophysical, Photochemical Properties of Peripherally Metallophthalocyanines Bearing (2-(Benzo[d] [1,3] Dioxol-5-Ylmethoxy) Phenoxy) Substituents

Theoretical and experimental investigations of complexation with BF₃.Et₂O effects on electronic structures, energies and photophysical properties of Anil and tetraphenyl (hydroxyl) imidazol

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New zinc phthalocyanine derivatives for nitrogen dioxide sensors: A theoretical optoelectronic investigation

Cited by 27 publications

References 38 publications

Resonant Plasmon‐Enhanced Absorption of Charge Transfer Complexes in a Metal–Organic Monolayer

Resonant Plasmon‐Enhanced Absorption of Charge Transfer Complexes in a Metal–Organic Monolayer

Synthesis, DFT Calculations, Photophysical, Photochemical Properties of Peripherally Metallophthalocyanines Bearing (2-(Benzo[d] [1,3] Dioxol-5-Ylmethoxy) Phenoxy) Substituents

Theoretical and experimental investigations of complexation with BF3.Et2O effects on electronic structures, energies and photophysical properties of Anil and tetraphenyl (hydroxyl) imidazol

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Theoretical and experimental investigations of complexation with BF₃.Et₂O effects on electronic structures, energies and photophysical properties of Anil and tetraphenyl (hydroxyl) imidazol