Dipole moments, charge-transfer parameters, and ionization potentials of the methyl-substituted benzene–tetracyanoethylene complexes

Chan, R. K.; Liao, S. C.

doi:10.1139/v70-045

Cited by 33 publications

(10 citation statements)

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“…In addition, the authors showed a linear correlation between the ionization potential of the donor species and the electronic transition energies of the charge transfer complexes investigated. 31 In fact, in Figure 2a, it can be observed a linear correlation between the transition energies (in cm -1 ) and the experimental ionization potentials, 32 where the relation is hν (cm -1 ) = 0.45IP -11105 (R 2 = 0.9993). Figure 2b shows the comparison of the experimental values observed for the charge transfer transition bands and the respective calculated values obtained by TDDFT.…”

Section: Resultsmentioning

confidence: 91%

“…The trend observed for the transition energies of the complexes formed between TCNE and substituted anilines is very similar to the well behaved trend observed for the complexes of TCNE with methyl substituted benzenes and TCNE. Chan and Liao 31 showed in a systematic study for 13 substituted benzenes with increasing number of methyl groups, that the maximum absorption values range from 385 nm for TCNE-benzene complex to 535 nm for TCNE-hexamethylbenzene in CCl 4 solution. In addition, the authors showed a linear correlation between the ionization potential of the donor species and the electronic transition energies of the charge transfer complexes investigated.…”

Section: Resultsmentioning

confidence: 99%

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Spectroscopic Characterization of Charge Transfer Complexes of TCNE with Aromatic Amines - The First Step of Tricyanovinylation Reaction

Monezi¹,

Ando²

2016

J. Braz. Chem. Soc.

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The first step of electrophilic aromatic substitution reactions generally involves the formation of charge transfer complexes. Tetracyanoethylene (TCNE) in the presence of aromatic amines forms π-type complexes that subsequently lead to tricyanovinylation reaction. Although this kind of reaction was investigated in the past, the spectroscopic characterization of the charge transfer complexes is still lacking, since in many cases the first step of the reaction is too fast to allow their characterization by conventional techniques. In this paper, it is shown the UV-Vis and resonance Raman characterization of the charge transfer complexes formed between TCNE and substituted anilines. The magnitude of the charge transfer could be linearly correlated with the electronic absorpion energies, as well as to the Raman shifts observed for the characteristic ν(C≡N) mode of TCNE. In addition, the results were correlated to ionization potentials of amines, and theoretical calculations by density functional theory/time-dependent density functional theory (DFT/TDDFT) methods were performed to support the experimental data.

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Section: Resultsmentioning

confidence: 91%

Section: Resultsmentioning

confidence: 99%

Spectroscopic Characterization of Charge Transfer Complexes of TCNE with Aromatic Amines - The First Step of Tricyanovinylation Reaction

Monezi¹,

Ando²

2016

J. Braz. Chem. Soc.

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“…[93,94] In other words, smaller IP (larger EA) values state easier injection of holes into the emissive layers from the hole (electron) transport layer. In general, the lower IP and higher EA mean better hole and electron transport.…”

Section: Ionization Potentials and Electron Affinitiesmentioning

confidence: 99%

“…In general, the lower IP and higher EA mean better hole and electron transport. [93,94] In other words, smaller IP (larger EA) values state easier injection of holes into the emissive layers from the hole (electron) transport layer. [48] All adiabatic ionization potential (IPa), vertical ionization potential (IPv), adiabatic electron affinity (EAa), and vertical electron affinity (EAv) of porphyrin and metallated porphyrins are computed and presented in Table 2.…”

Section: Ionization Potentials and Electron Affinitiesmentioning

confidence: 99%

Electronic, optical, and charge transfer properties of porphyrin and metallated porphyrins in different media

Üngördü

2019

Int J of Quantum Chemistry

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Porphyrin and M-Porphyrin (M = Fe 2+ , Co 2+ , Ni 2+ , Cu 2+ , and Zn 2+ ) complexes were designed to examine their organic light-emitting diode (OLED) properties. All calculations were performed in different media, which are gas, benzene, DMSO, and water phases. The calculations of both porphyrin and its metal complexes as a monomer form were performed at B3LYP/6-31G(d) level by using the Gaussian 16 and GaussView 6 package programs. On the other hand, emission calculations for the monomer form and dimer form computations of the studied compounds were carried out at PBE0/TZP and B3LYP/TZP levels, respectively, by using Amsterdam density functional (ADF) 2019 package program. The OLED tensors of the mentioned molecules, which are emission energies, reorganization energies (λ e and λ h ), the ionization potentials and the electron affinities (adiabatic and vertical), the effective transfer integrals (V e and V h ), and the charge transfer rates (W e and W h ), were calculated to evaluate the OLED behaviors and determine the best OLED structure. K E Y W O R D Scharge transfer rate, OLED material, porphyrin, reorganization energy, transfer integral | INTRODUCTIONThe improvement of organic light-emitting diodes (OLEDs) including π-conjugated systems has been of interest over the past decade due to their economical and efficient applications in next-generation display technology and lighting field. [1][2][3][4][5][6][7][8][9] These systems can consist of metal-free or metallated compounds. [10][11][12][13][14][15][16][17] Fundamentally, used compounds in OLED structure have been classified as electron-transporting layers (ETL), [18][19][20] hole-transporting layers (HTL), [18,19] and emissive layers (EL). [18,19] In addition to these layers, there are electron injection layer (EIL), [21,22] electron blocking layer (EBL), [23,24] hole injection layer (HIL), [25,26] and hole blocking layer (HBL) [27,28] between cathode and anode. EL materials are found between ETL and HTL materials and emit light from red to blue depending on the wavelength of the emission. [29][30][31][32][33] N,N 0 -diphenyl-N,N 0 -bis (3-methyl phenyl)-(1,10-biphenyl)-4,4 0 -diamine (TPD) [34][35][36] and tris(8-hydroxyquinolinato)aluminum(III) (Alq3) [37][38][39] are a typical HTL and a ETL material, respectively. While TPD is metal-free molecules, Alq3 is metallated organic molecules. Researchers investigating OLEDs have studies on determining alternative molecules that are superior to these compounds. [40][41][42][43][44][45][46][47][48] Additionally, color properties of emitter materials in EL layer have been studied. [49][50][51][52] Recently, the scientists have focused on improving the materials having a high charge transfer rate and exhibiting strong emission in the visible region to increase the performance of OLEDs. [53][54][55][56][57][58][59] For this purpose, they have modified the compounds via using the metal or substituent. [15,[60][61][62][63][64] Porphyrin is a planar, aromatic macrocyclic ring consisting of four pyrrole units havin...

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“…The ionization potential and electron affinity are distinct properties that can be calculated by DFT to estimate the energy barrier for the injection of holes and electrons. The lower ionization potential revealed that material would be better as hole transporter [47] while higher electron affinity leads to be a better electron transport. We have tabulated the adiabatic ionization potential (IPa), vertical ionization potential (IPv), adiabatic electron affinity (EAa), and vertical .81 eV, respectively revealing decreased electron injection barrier compared to the parent molecule.…”

Section: Ionization Potential and Electron Affinitymentioning

confidence: 99%

Modeling of efficient charge transfer materials of 4,6-di(thiophen-2-yl)pyrimidine derivatives: Quantum chemical investigations

Irfan¹

2014

Computational Materials Science

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Dipole moments, charge-transfer parameters, and ionization potentials of the methyl-substituted benzene–tetracyanoethylene complexes

Cited by 33 publications

References 10 publications

Spectroscopic Characterization of Charge Transfer Complexes of TCNE with Aromatic Amines - The First Step of Tricyanovinylation Reaction

Spectroscopic Characterization of Charge Transfer Complexes of TCNE with Aromatic Amines - The First Step of Tricyanovinylation Reaction

Electronic, optical, and charge transfer properties of porphyrin and metallated porphyrins in different media

Modeling of efficient charge transfer materials of 4,6-di(thiophen-2-yl)pyrimidine derivatives: Quantum chemical investigations

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