Transistor Properties of Charge-Transfer Complexes─Combined Requirements from Energy Levels and Orbital Symmetry

Liu, Baiyan; Fan, Shuxiang; Huang, Ruoxi; Kawamoto, Tadashi; Mori, Takehiko

doi:10.1021/acs.jpcc.2c08317

Cited by 4 publications

(11 citation statements)

References 69 publications

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“…Even 2,3-DAN (−5.22 eV) is a stronger donor than quarterthiophene (−5.3 eV) . Such low oxidation potential allows us to exclude the possibility of hole transport being impeded due to the hole transport limit . 1-MAP is as strong as these DAN derivatives.…”

Section: Resultsmentioning

confidence: 99%

“…When the energy level of a donor is situated near the hole transport limit (−5.6 eV), the exponential factor becomes 0.07. From this viewpoint, the observed current is less than one-tenth, and it is reasonable that the hole transport is practically lost . Taking into account the effective transfers, reorganization energies, and injection barriers, this estimation explains the observed transistor properties sufficiently.…”

Section: Discussionmentioning

confidence: 99%

“…When half-molecule overlap is achieved, p-channel transport is observed. Ambipolar transport is realized in the case of low-symmetry molecular overlaps and when the donor is an oligomer …”

Section: Discussionmentioning

confidence: 99%

“…Furthermore, we have also examined complexes of other DAN isomers: 2,6-DAN and 2,3-DAN. Due to the low oxidation potentials of these donors, we can investigate the transistor properties without considering the hole transport limit of their energy levels …”

Section: Introductionmentioning

confidence: 99%

“…Due to the low oxidation potentials of these donors, we can investigate the transistor properties without considering the hole transport limit of their energy levels. 45 The transistor characteristics observed in these mixed-stack complexes are not balanced ambipolar. This unbalance of charge carrier polarity is explained by elucidating the significance of orbitals other than HOMO and LUMO from the viewpoint of Larsson partition theory.…”

Section: Introductionmentioning

confidence: 99%

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Charge Polarity Control in Organic Transistors of Mixed and Segregated Complexes Based on Diaminonaphthalene and Pyrene

Mallela,

Kawamoto,

Mori

2023

ACS Appl. Mater. Interfaces

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Organic cocrystals of diaminonaphthalene (DAN) and diaminopyrene (DAP) with bromanil (BA) and tetracyanoquinodimethane (TCNQ) are an exemplar system for understanding the charge-transport process, where from the viewpoint of partition theory, orbital symmetry plays a crucial role in controlling the carrier charge polarity of transistors. In the mixed-stack complexes of BA and other p-quinone acceptors, a comparatively weak donor, 1,5-DAN, shows p-channel characteristics owing to the counteractive contribution of the next highest occupied molecular orbital for electron transport. This characteristic behavior occurs because the BA molecule, situated on top of the amino group, overlaps with half of the DAN molecule. By contrast, the BA and TCNQ complexes of a stronger donor, 1,6-DAP, exhibit n-channel transport due to the cooperative path and orthogonal orbitals. Similarly, TCNQ complexes of variously substituted DAN show n-channel transport, where the TCNQ molecules are located on top of the DAN molecules. However, when the carbon electrodes of (1,5-DAN)(BA) are replaced by silver, electron transport appears due to the competitive effect of the Schottky barriers. In a highly conducting segregated complex of (1,6-DAP)(TCNQ), ambipolar transistor characteristics are observed without subtracting the bulk current by using carefully prepared thin-film transistors.

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Section: Resultsmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

“…When half-molecule overlap is achieved, p-channel transport is observed. Ambipolar transport is realized in the case of low-symmetry molecular overlaps and when the donor is an oligomer …”

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Charge Polarity Control in Organic Transistors of Mixed and Segregated Complexes Based on Diaminonaphthalene and Pyrene

Mallela,

Kawamoto,

Mori

2023

ACS Appl. Mater. Interfaces

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Pyrazine‐Based Chiral AIE Electronic Acceptors for Real‐Time Monitoring Hierarchical Self‐Assembly and Tuning Emissions through Intermolecular Charge‐Transfer Effects

He,

Xie,

Hong

et al. 2024

Advanced Optical Materials

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Development of chiral aggregation‐induced emission (AIE) materials toward hierarchical self‐assembly is crucial to reveal the origin and evolution of life. In this work, a pair of chiral AIE enantiomers is fabricated by attaching the typical AIE units to the chiral binaphthyl core via a single bond linkage. The AIE behavior is inherited from the introduced AIE unit while the binaphthyl unit can not only improve the photo‐physical properties but also provide the whole molecules with chirality. Moreover, as driven by the dipolar structure and chirality of the AIEgens, the hierarchical self‐assembly with different morphologies such as spheres, ribbons or fibers, flowers, and even bigger structures with various sizes can be dynamically monitored with the assembled time, which provided a favorable evidence to study the structural evolution from molecular level to a higher‐level structure. On the other hand, these AIEgens can act strong electronic acceptors due to the introduced AIE unit. By complexing them with strong electronic donors, the resulting intermolecular charge transfer can induce remarkable red emissions with the tunable properties which is much different from their individuals. This enabled it as a facile, economic, and flexible approach to develop organic photoelectric materials.

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Ferrocene-Based Organic Semiconductors: Evaluating Intermolecular Transfer Integrals and Transistor Properties

Sano,

Naito,

Katagiri

et al. 2024

ACS Appl. Electron. Mater.

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Ferrocene, with its unique redox properties and stability, offers promising potential for use in semiconductor layers of organic transistors. However, it has not previously been applied due to its high vapor pressure and inability to form thin films. We have successfully fabricated thin-film transistors by introducing appropriate substituents into ferrocene and increasing the molecular weight, thereby suppressing its sublimation properties. Based on the crystal structures at room temperature, we have calculated the intermolecular transfer integrals using density functional theory. We have evaluated the carrier-path anisotropy (dimensionality of the electronic structure), as well as thin-film transistor properties. Ferrocene derivatives having small substituents such as phenyl groups form herringbone-like molecular arrangements, realizing two-dimensional carrier paths. In contrast, ferrocene derivatives with bulky substituents such as anthryl groups form one-dimensional uniform stacks, though the transfer integrals of all ferrocene derivatives are relatively small below 10 meV. Our evaluation have confirmed the switching of the drain currents in the forward-back scan of the gate voltage during transistor operations, indicating that the reversible redox property of Fc/Fc + in the ferrocene units are realized even in the solid state.

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Transistor Properties of Charge-Transfer Complexes─Combined Requirements from Energy Levels and Orbital Symmetry

Cited by 4 publications

References 69 publications

Charge Polarity Control in Organic Transistors of Mixed and Segregated Complexes Based on Diaminonaphthalene and Pyrene

Charge Polarity Control in Organic Transistors of Mixed and Segregated Complexes Based on Diaminonaphthalene and Pyrene

Pyrazine‐Based Chiral AIE Electronic Acceptors for Real‐Time Monitoring Hierarchical Self‐Assembly and Tuning Emissions through Intermolecular Charge‐Transfer Effects

Ferrocene-Based Organic Semiconductors: Evaluating Intermolecular Transfer Integrals and Transistor Properties

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