Effect of dihydropyrazine on structures and charge transport properties of N-heteropentacenes matters: A theoretical investigation

Chen, Xiankai; Zou, Lu; Fan, Jian Xun; Zhang, Shou Feng; Ren, Ai Min

doi:10.1016/j.orgel.2012.08.035

Cited by 17 publications

(9 citation statements)

References 51 publications

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“…In addition, substitution of heteroatom for carbon atom on the ring backbone of TIPS-PEN also significantly affects the transport and injection of charge carriers in organic semiconductor materials. Our research group investigated this issue specifically. , In this study, we concentrate on only the tunable effect of intra- or extra-ring backbone-based halogenated TIPS-PEN heteroatom substitution on the transport and injection of the charge carrier.…”

Section: Introductionmentioning

confidence: 99%

Theoretical Study on Charge Transport Properties of Intra- and Extra-Ring Substituted Pentacene Derivatives

et al. 2016

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A series of pentacene derivatives, halogen-substituted and thiophene- and pyridine-substituted, have been studied with a focus on the electronic properties and charge transport properties using density functional theory and classical Marcus charge-transfer theory. The transport properties of holes and electrons have been studied to get insight into the effect of halogenation and heteroatom substitution on transport and injection of charge carriers. The calculation results revealed that fluorination and chlorination can effectively lower the lowest unoccupied molecular orbital (LUMO) level, modulate the hole and electron reorganization energy, improve the stacking mode of the crystal structure, and enhance the ambipolar characteristic. Chlorination gives a better ambipolar characteristic. On the basis of halogen substitution, the substitution of terminal benzene ring of triisopropyl-silylethynyl-pentacene (TIPS-PEN) by a thiophene or pyridine will greatly lower the LUMO level and improve the stacking mode, leading to more suitable ambipolar materials. Hence, both intra- and extra-ring substitution are favorable to enhance the ambipolar transport property of TIPS-PEN.

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Section: Introductionmentioning

confidence: 99%

Theoretical Study on Charge Transport Properties of Intra- and Extra-Ring Substituted Pentacene Derivatives

et al. 2016

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“…Detailed and comprehensive discussions can be seen from the Supporting Information. First, all of these molecules are classified as potential p-type organic semiconductor materials with good antioxidation capacity due to their low hole injection energy barriers 25 (Au electrode with 5.1 eV work function is taken as the source and drain electrode in our case) and high IP(a)s. The high electron injection energy barriers and the very small EA(a) values determine their poor n-type behavior and the instability of their radical anions in ambient atmosphere. Second, TAS-ADTs are better in photostability and antioxidation capacity because of their wider HOMO/LUMO energy gaps and higher IP(a)s than those of TAS-PENs.…”

Section: Resultsmentioning

confidence: 99%

“…One can see that the k ct is predominantly determined by two important parameters: the local electron–phonon coupling (the overall strength is commonly expressed by reorganization energy λ) and the charge-transfer integral V . In organic solids, the intermolecular λ are much smaller than the intramolecular one; , thus, in this study, only the intramolecular λ is considered. Here, the intramolecular reorganization energies are evaluated from both the adiabatic potential-energy surfaces (AP) and the normal mode analysis (NM). , The geometry optimizations of the neutral and charged states and the corresponding vibrational frequency analyses of all molecules were carried out using Gaussian 09 program package at the B3LYP/6-31G** level of theory .…”

Section: Theoretical Methodsmentioning

confidence: 99%

“…40 Here, n ̅ j = 1/(e ℏω j /k B T − 1) contributes the occupation number of the jth intramolecular vibrational mode, ω j is the frequency, k B is the Boltzmann constant, S j represents the Huang−Rhys factor measuring the local electron−phonon coupling strength, and V is the charge-transfer integral (electronic coupling). One can see that the k ct is predominantly determined by two important parameters: the local electron−phonon coupling (the overall strength is commonly expressed by reorganization energy λ) and the charge-transfer integral V. In organic solids, the intermolecular λ are much smaller than the intramolecular one; 6,25 thus, in this study, only the intramolecular λ is considered. Here, the intramolecular reorganization energies are evaluated from both the adiabatic potential-energy surfaces (AP) 26 and the normal mode analysis (NM).…”

Section: Theoretical Methodsmentioning

confidence: 99%

“…Up to now, its field-effect hole mobility has achieved 6.8 cm 2 V –1 s –1 via superhydrophobic micropillar flow-coating method . Spurred by these delightful results, researchers applied this trialkylsilylethynyl (TAS) functionalization approach experimentally and theoretically to design and synthesize other fused systems with large and planar π surfaces, such as polycyclic aromatic hydrocarbons, ,− N -heteroacenes, ,− S -heteroacenes, − and O -heteroacenes . Among these materials, two classes of molecules attract our attention: (i) TAS-functionalized pentacene (PEN) and (ii) TAS-functionalized anthradithiophene (ADT).…”

Section: Introductionmentioning

confidence: 99%

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Theoretical Investigations on Molecular Packing Motifs and Charge Transport Properties of a Family of Trialkylsilylethynyl-Modified Pentacenes/Anthradithiophenes

Zhang

Ren

et al. 2018

J. Phys. Chem. C

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A family of trialkylsilylethynyl (TAS)-functionalized pentacenes (PENs) and anthradithiophenes (ADTs) are of immense interest due to their good solubility and air stability for uses in optoelectronic devices. Different TAS-substituted PENs and ADTs would result in different crystal packing motifs and carrier transport properties. Quantum nuclear-enabled hopping model combined with molecular dynamics (MD) simulations was used to investigate the effects of the chemical modifications on the carrier transport properties. The disorder-free hole mobilities show that 6,13-bis(trialkylsilylethynyl)anthradithiophenes (TAS-ADTs) own better intrinsic hole transport behaviors than 6,13-bis(trialkylsilylethynyl)pentacenes (TAS-PENs). The MD simulations show that in comparison with TAS-PENs, the thermal disorder effects are less significant for TAS-ADTs; this is probably due to the C–H···S hydrogen bonds, which are thought to stabilize the molecules in crystal environments. Furthermore, the syn-TAS-ADTs show more serious nonlocal electron–phonon interactions than the anti-TAS-ADTs, which could be ascribed to the larger S···S overlap between neighboring molecules in the syn-TAS-ADTs. Additionally, symmetry-adapted perturbation theory and Hirshfeld surface analyses were performed to characterize the effects of noncovalent interactions on packing motifs. The results indicate that the C–H···π interaction, the balance relationship between electrostatic, induction, dispersion, and exchange repulsion interactions, and the C–H···S hydrogen bonds are responsible for the very different crystal packing motifs between these materials.

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Ten Years of N‐Heteropentacenes as Semiconductors for Organic Thin‐Film Transistors

2014

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Introducing N atoms to the pentacene backbone leads to N-heteropentacenes, whose properties can be tuned by changing the number, position and valence state of N atoms in the pentacene backbone. With a rapid development in recent years, N-heteropentacenes and their derivatives have arisen as a new family of organic semiconductors with high performance in organic thin-film transistors (OTFTs). This article reviews the research efforts of developing N-heteropentacenes into organic semiconductors starting from 2003 with emphasis on the work of the author's group since 2009. The structure-property relationship and design rationale are highlighted based on an overview of reported organic semiconductors of N-heteropentacenes.

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Effect of dihydropyrazine on structures and charge transport properties of N-heteropentacenes matters: A theoretical investigation

Cited by 17 publications

References 51 publications

Theoretical Study on Charge Transport Properties of Intra- and Extra-Ring Substituted Pentacene Derivatives

Theoretical Study on Charge Transport Properties of Intra- and Extra-Ring Substituted Pentacene Derivatives

Theoretical Investigations on Molecular Packing Motifs and Charge Transport Properties of a Family of Trialkylsilylethynyl-Modified Pentacenes/Anthradithiophenes

Ten Years of N‐Heteropentacenes as Semiconductors for Organic Thin‐Film Transistors

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