Influence of methoxy groups on the properties of 1,1-bis(4-aminophenyl)cyclohexane based arylamines: experimental and theoretical approach

Keruckas, Jonas; Lygaitis, Ramūnas; Simokaitienė, Jūratė; Gražulevičius, Juozas V.; Jankauskas, Vygintas; Sini, Gjergji

doi:10.1039/c2jm14387a

Cited by 34 publications

(40 citation statements)

References 46 publications

(56 reference statements)

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“…4 During the last years, much attention has been paid to derivatives of triphenylamine because of their good holetransporting properties, making these materials promising candidates for optoelectronic and electronic devices. [6][7][8] However, recent studies [8][9][10] have reported on methoxy substituted compounds exhibiting larger hole-mobilities as compared to the nonsubstituted ones. We focus here on the influence of methoxy-and methyl substituents.…”

Section: Introductionmentioning

confidence: 99%

“…Methoxy substitutions have been found to enhance the dipole moment and decrease the charge mobility of substituted compounds as compared to the non-substituted ones. 9,10 The contradictory effects of the methoxy substitutions on the hole-mobilities of amorphous materials [6][7][8][9][10] suggest consequently a subtle balance between effects playing in opposite directions. The improvement of the hole-transporting properties upon methoxy substitutions has been suggested to partly stem from the (-C-H….π, N, O) hydrogen bonds established in the hole-transporting materials by means of methoxy groups.…”

Section: Introductionmentioning

confidence: 99%

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Can hydrogen bonds improve the hole-mobility in amorphous organic semiconductors? Experimental and theoretical insights

et al. 2015

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Five hole-transporting triphenylamine derivatives containing methoxy and methyl groups are synthesized and investigated. The hole-mobility increases in the presence of methyl-and methoxy substituents, exceeding 10 -2 cm 2 /Vs in the case of the methyl groups. Quantum mechanical calculations on these compounds indicate very different dipole moments and intermolecular interaction strengths, with intriguing correlations to the trend in hole-mobility. Temperature dependent hole-mobility measurements indicate disorder dominated hole transport. The values of the energetic disorder parameter (σ) decrease upon methyl and methoxy substitutions despite the increase in dipole moments. This trend is discussed as a function of the interaction energy between adjacent molecules, the dipole moment, the molecular polarizability, and the conformational degree of freedom. Our results indicate that the global decrease of σ upon methyl and methoxy substitutions is dominated by the the larger decrease in the geometrical randomness component of the energetic disorder. A direct correlation is established between the decrease in geometrical randomness and the increase in intermolecular interaction energies, mainly stemming from the additional C-H….π,O,N hydrogen bonds induced by methyl and methoxy groups. the dipolar-moments on the energetic disorder, 6,7 methoxy substitutions are then expected to result in degraded-or improved charge transport properties, partly depending on the (respectively) important-or negligible increase of the molecular dipole moments. As will be shown in this study, the

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Can hydrogen bonds improve the hole-mobility in amorphous organic semiconductors? Experimental and theoretical insights

et al. 2015

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“…2,7-Dimethoxycarbazole (1a, 0.40 g, 1.8 mmol), 2-ethylhexylbromide (0.38 g, 2.1 mmol), potassium carbonate (0.10 g, 0.70 mmol), potassium hydroxide (0.30 g, 5.3 mmol) and catalytic amount of tetrabutylammonium hydrogensulfate were refluxed (2 h) in acetone (14 ml). 13 The structures of 3a-b were also proven by X-ray crystallography. The organic layer was dried over anhydrous Na 2 SO 4 , filtered and the solvents were removed.…”

Section: Methodsmentioning

confidence: 92%

“…It is known that introduction of methoxy groups into the structures of aromatic amines as well as the attachment of methoxy-substituted diphenylamino groups to the carbazole moieties lead to the decrease of the ionization potential. 12,13 The para-methoxy substituted derivatives also showed the highest hole mobilities. The hole-injection barrier differences can strongly affect the efficiency of the devices.…”

Section: Introductionmentioning

confidence: 98%

“…11,12 The possibility to monitor ionization potentials is also important in the fabrication of OLEDs. 12,13 The effect of the methoxy substitution in carbazole derivatives on their photophysical and photoelectrical properties, to the best of our knowledge, has not yet been studied. The role of the methoxy groups is found to be related to the mesomeric (p-donor) effect and the possibility to establish hydrogen bonds.…”

Section: Introductionmentioning

confidence: 99%

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Structure–property relationship of isomeric diphenylethenyl-disubstituted dimethoxycarbazoles

et al. 2015

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ARTICLE This journal isIsomeric 3,6-dimethoxy-and 2,7-dimethoxycarbazoles containing diphenylethenyl moieties were synthesized by condensation of the appropriate dimethoxycarbazoles with diphenylacetaldehyde. The solid-state structures and the molecular order of the compounds were proven by X-ray crystallography. Both compounds were found to be capable of glass formation with the comparable glass transition temperatures (70-71 o C). They exhibited high thermal stabilities, with the 5 % weight loss temperatures exceeding 375 o C. The isomer having diphenylethenyl groups at C-3 and C-6 positions and methoxy groups at C-2 and C-7 positions (3a) exhibited aggregation-induced emission (AIE), while its counterpart having diphenylethenyl groups at C-2 and C-7 positions and methoxy groups at C-3 and C-6 positions (3b) showed the opposite effect, i.e. aggregation-caused quenching (ACQ). The derivative 3b showed superior charge transporting properties. Time-of-flight hole drift mobilities in its layers approached 10 -3 cm 2 /Vs at high electric fields. A comparative theoretical analysis of the compounds was performed using density functional theory (DFT) and time-dependent DFT calculations. They proved more effective π-conjugation in the derivative of 3,6-dimethoxycarbazole (3b), which was also observed by UV and fluorescence spectroscopies. The theoretical study revealed relatively low ground state dipole moment of 0.69 D of the isomer 3b, while its counterpart (3a) showed much higher ground state dipole moment of 5.98 D. The difference in polarity was found to have the crucial effect on the molecular arrangement in the crystals and consequently, on the thermal transitions and charge-transporting properties.

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The Application of a Small‐Molecule‐Based Ternary Memory Device in Transient Thermal‐Probing Electronics

Zhou

Dong

et al. 2016

Advanced Materials

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Influence of methoxy groups on the properties of 1,1-bis(4-aminophenyl)cyclohexane based arylamines: experimental and theoretical approach

Cited by 34 publications

References 46 publications

Can hydrogen bonds improve the hole-mobility in amorphous organic semiconductors? Experimental and theoretical insights

Can hydrogen bonds improve the hole-mobility in amorphous organic semiconductors? Experimental and theoretical insights

Structure–property relationship of isomeric diphenylethenyl-disubstituted dimethoxycarbazoles

The Application of a Small‐Molecule‐Based Ternary Memory Device in Transient Thermal‐Probing Electronics

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