Charge-transfer complexes of sulfur-rich acceptors derived from birhodanines

Fan, Shuxiang; Kiyota, Yasuhiro; Iijima, Kazutoshi; Ryo, Suho; Kawamoto, Tadashi; Gal, Yann Le; Lorcy, Dominique; Mori, Takehiko

doi:10.1039/c9ce00952c

Cited by 4 publications

(3 citation statements)

References 49 publications

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“…363 In general, complexes of low-symmetry acceptors realize ambipolar transistors. [379][380][381][382][383][384] Charge polarity of (anthracene)(TCNQ) shows a remarkable temperature dependence. 385 At room temperature the anthracene molecules can rotate within the molecular plane, and become seriously disordered.…”

Section: Donor-acceptor Complexesmentioning

confidence: 99%

Small-molecule ambipolar transistors

Higashino

Mori

2022

Phys. Chem. Chem. Phys.

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Section: Donor-acceptor Complexesmentioning

confidence: 99%

Small-molecule ambipolar transistors

Higashino

Mori

2022

Phys. Chem. Chem. Phys.

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“…The situation is not largely different in the triclinic phase. , There is a correlation between the observed mobility and t eff (Figure ); more than 0.1 cm 2 V –1 s –1 is observed only when t eff > 60 meV, and μ < 10 –3 cm 2 V –1 s –1 or no transistor properties at t eff < 20 meV. Another example of small intrastack transfer integrals (<10 meV) has been found in birhodanine complexes (SS-Et in Figure b), where the charge polarity is related to the interstack DD and AA interactions . This is exceptional because the interstack DD and AA interactions are ordinarily less than 5 meV.…”

Section: Discussionmentioning

confidence: 82%

“…Another example of small intrastack transfer integrals (<10 meV) has been found in birhodanine complexes (SS-Et in Figure 4b), where the charge polarity is related to the interstack DD and AA interactions. 64 This is exceptional because the interstack DD and AA interactions are ordinarily less than 5 meV. Energy levels of 4T and tetramethylbenzidine (TMB) complexes are depicted in Figure 6.…”

Section: ■ Discussionmentioning

confidence: 99%

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

et al. 2023

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Tetracyanoquinodimethane (TCNQ) complexes of fluorene, dibenzofuran, dibenzothiophene, terphenyl, dithienothiophene, and carbazole show n-channel transistor properties, whereas that of diaminoterphenyl and phenothiazine exhibits ambipolar characteristics. Ambipolar transport is observed when the highest occupied molecular orbital (HOMO) level of the donor–acceptor complex is located above the ordinary hole transport limit. Since the HOMO of the charge-transfer complex is deeper than that of the component donor owing to the charge-transfer interaction, not all hole-transporting materials show hole transport in the charge-transfer complexes. In addition, the effective (super-exchange) transfer integrals have to be sufficiently large; this is frequently not satisfied when the donor HOMO is practically orthogonal to the acceptor’s lowest unoccupied molecular orbital (LUMO). By applying these criteria to calculations starting from the crystal structures, transistor properties of mixed stack charge-transfer complexes are explained.

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Band Engineering and Majority Carrier Switching in Isostructural Donor–Acceptor Complexes DPTTA‐F_XTCNQ Crystals (X = 1, 2, 4)

et al. 2019

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Three isostructural donor–acceptor complexes DPTTA‐FXTCNQ (X = 1, 2, 4) are investigated experimentally and theoretically. By tuning the number of F atoms in the acceptor molecules, the resulting complexes display a continuous down shift of the valence band maximum, conducting band minimum, and optical bandgap. The majority carriers convert from hole (DPTTA‐F1TCNQ), balanced hole, and electron (DPTTA‐F2TCNQ) to electron (DPTTA‐F4TCNQ). This result shows that band engineering can be realized easily in the donor–acceptor complex systems by tuning the electron affinity of the acceptor. The bandgaps of these three complexes vary from 0.31 to 0.41 eV; this narrow bandgap feature is crucial for achieving high thermoelectric performance and the unintentional doping in DPTTA‐F4TCNQ leads to the effective suppression of the bipolar cancelling effect on the Seebeck coefficient and the highest power factor.

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Charge-transfer complexes of sulfur-rich acceptors derived from birhodanines

Abstract: The title acceptors form charge-transfer complexes with mixed stacks, whose transistors are affected by the S–S interaction between the acceptors.

Cited by 4 publications

References 49 publications

Small-molecule ambipolar transistors

Small-molecule ambipolar transistors

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

Band Engineering and Majority Carrier Switching in Isostructural Donor–Acceptor Complexes DPTTA‐F_XTCNQ Crystals (X = 1, 2, 4)

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Charge-transfer complexes of sulfur-rich acceptors derived from birhodanines

Abstract: The title acceptors form charge-transfer complexes with mixed stacks, whose transistors are affected by the S–S interaction between the acceptors.

Cited by 4 publications

References 49 publications

Small-molecule ambipolar transistors

Small-molecule ambipolar transistors

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

Band Engineering and Majority Carrier Switching in Isostructural Donor–Acceptor Complexes DPTTA‐FXTCNQ Crystals (X = 1, 2, 4)

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Product

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Band Engineering and Majority Carrier Switching in Isostructural Donor–Acceptor Complexes DPTTA‐F_XTCNQ Crystals (X = 1, 2, 4)