Effect of Molecular Orbital Distributions on Charge Transport   Properties   of Polymers Doped with Triphenylamine Derivatives

Aratani, Sukekazu; Kawanishi, Tsuneaki; Kakuta, Atsushi

doi:10.1143/jjap.35.2184

Cited by 17 publications

(9 citation statements)

References 11 publications

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“…Several authors have used computational methods to address the structure-property issues in TPD-derived molecular materials, with particular emphasis on the geometric and electronic changes which accompany oxidation/hole transport phenomena. [1][2][3][4][5][6][7] In the case of N,N,N9,N9-tetra(aryl)-1,19biphenyl-4,49-diamines, which form one of the most widely employed classes of hole transport material the key conformational parameters (Fig. 1) can be considered to be: the torsion angle between the ring systems of the biphenyl moiety, i.e.…”

Section: Introductionmentioning

confidence: 99%

Towards an understanding of structure–property relationships in hole-transport materials: The influence of molecular conformation on oxidation potential in poly(aryl)amines

et al. 2005

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The influence of molecular conformation on the oxidation (ionisation) potential and electronic structure associated with several TPD-style hole transport materials has been assessed through a combination of single crystal X-ray diffraction, electrochemical and spectroelectrochemical methods and DFT calculations. The introduction of methyl groups can be used to tune the ionisation potential of these molecular species through a combination of electronic (inductive) and thermodynamic effects, while the conformation of the biphenyl portion of the molecular framework is found to play the greatest role in determining the Marcus-type reorganisation energy associated with the charge transport process on the molecular level.

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Section: Introductionmentioning

confidence: 99%

Towards an understanding of structure–property relationships in hole-transport materials: The influence of molecular conformation on oxidation potential in poly(aryl)amines

et al. 2005

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“…Organic charge-transporting materials are important for electrical and optical applications such as organic photoconductor, electroluminescence, and electrochromic devices [7][8][9] . The charge transporting materials are divided into two groups; hole and electron transporting materials, abbreviated as HTM and ETM.…”

Section: Introductionmentioning

confidence: 99%

Condensation polymerization of triphenylamine with carbonyl compounds

Son¹,

Nakao

Oginö

et al. 1999

Macromol. Chem. Phys.

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SUMMARY: Triphenylamine (TPA) was reacted with carbonyl compounds such as formaldehyde, butyraldehyde, benzaldehyde, and acetone in the presence of an acid catalyst. 1 H and 13 C NMR spectra revealed that the carbonyl compounds react only at the p-position of TPA. The reactivity of formaldehyde with TPA is lower than that with phenol. If equal molar amounts of formaldehyde are reacted, however, TPA condensation proceeds to high molecular weight polymers, while phenol provides only low molecular weight compounds (up to 1 000). TPA-aldehyde polymers have glass transition temperatures in the range of 135 -176 8C. These polymers show good solubility and sufficient stability after film formation.

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“…The spatial distribution of HOMO and LUMO is usually used for describing the transport properties due to the fact that they dominate the coupling of the molecular bridge to electrodes . The spatial distribution of molecular orbitals for coumarin 102 and coumarin 153 under the effect of the EF from −0.30 to +0.30 V/Å has been displayed in Tables S1 and S2.…”

Section: Resultsmentioning

confidence: 99%

In silico investigation of the coumarin‐based organic semiconductors for the possible use in organic electronic devices

Siddiqui

2018

J of Physical Organic Chem

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First principle calculations were carried out to investigate the electron injection, electron coupling, electronic, and photophysical properties of two coumarin derivatives coumarin 102 and coumarin 153. The initial molecular geometries of both derivatives were optimized in the ground state using density functional theory in conjugation with B3LYP functional and 6-31G(d,p) basis set. The highest occupied molecular orbital (HOMO) of coumarin 102 and coumarin 153 were observed beneath the redox couple, whereas the lowest unoccupied molecular orbital (LUMO) of both coumarin derivatives were observed above the conduction band of TiO 2 . The time-dependent density functional theory has been used to calculate the excitation energies at PCM-CAM-B3LYP/6-31G(d,p) level. Based upon the calculation of hole reorganization energy λ h and electron reorganization energy λ e , it has been observed that both coumarin 102 and coumarin 153 are hole transport materials. The electronic coupling constant, electron injection, and light harvesting efficiencies of these coumarin derivatives are higher than coumarin. This clearly indicates that these derivatives would be excellent photosensitizers. Finally, the effect of electric field on the dipole moment, HOMO, LUMO, and HOMO-LUMO gap has been thoroughly observed to check the competency of these derivatives for the possible use in organic field effect transistors.

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Effect of Molecular Orbital Distributions on Charge Transport Properties of Polymers Doped with Triphenylamine Derivatives

Cited by 17 publications

References 11 publications

Towards an understanding of structure–property relationships in hole-transport materials: The influence of molecular conformation on oxidation potential in poly(aryl)amines

Towards an understanding of structure–property relationships in hole-transport materials: The influence of molecular conformation on oxidation potential in poly(aryl)amines

Condensation polymerization of triphenylamine with carbonyl compounds

In silico investigation of the coumarin‐based organic semiconductors for the possible use in organic electronic devices

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