Carrier Charge Polarity in Mixed-Stack Charge-Transfer Crystals Containing Dithienobenzodithiophene

Iijima, Kazutoshi; Sanada, Ryo; Yoo, Dongho; Sato, Ryo; Kawamoto, Tadashi; Mori, Takehiko

doi:10.1021/acsami.8b00416

Cited by 35 publications

(62 citation statements)

References 64 publications

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“…Cocrystals of donor and acceptor semiconductors have to face a twofold requirement. On one hand, their shape must be complementary, and on the other hand, their orbital symmetry must match for efficient charge transfer from the donor to the acceptor . The number of potential donor–acceptor combinations is extremely large, especially when considering 1:2, 1:3, or 2:1, 3:1 instead of simply 1:1.…”

Section: Charge Transportmentioning

confidence: 99%

Molecular Semiconductors for Logic Operations: Dead‐End or Bright Future?

et al. 2020

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The field of organic electronics has been prolific in the last couple of years, leading to the design and synthesis of several molecular semiconductors presenting a mobility in excess of 10 cm2 V−1 s−1. However, it is also started to recently falter, as a result of doubtful mobility extractions and reduced industrial interest. This critical review addresses the community of chemists and materials scientists to share with it a critical analysis of the best performing molecular semiconductors and of the inherent charge transport physics that takes place in them. The goal is to inspire chemists and materials scientists and to give them hope that the field of molecular semiconductors for logic operations is not engaged into a dead end. To the contrary, it offers plenty of research opportunities in materials chemistry.

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Section: Charge Transportmentioning

confidence: 99%

Molecular Semiconductors for Logic Operations: Dead‐End or Bright Future?

et al. 2020

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“…On the other hand, CT cocrystals that consist of mixed stacks generally behave as semiconductors or insulators . Recently there has been increasing interest in the semiconducting and photoconductive properties of mixed‐stack cocrystals. Large charge‐carrier mobility values, µ , have been reported for several examples using space‐charge limited current (SCLC) or field‐effect transistor (FET) measurements, including coronene:TCNQ ( µ SCLC = 0.3 cm 2 V −1 s −1 ) and DBTTF:TCNQ (DBTTF = dibenzotetrathiafulvalene; TCNQ = 7,7,8,8‐tetracyanoquinodimethane) ( µ e,FET = 1.0 cm 2 V −1 s −1 ) .…”

Section: Introductionmentioning

confidence: 99%

Charge‐Transport Properties of F₆TNAP‐Based Charge‐Transfer Cocrystals

Dasari

Wang

Wiscons

et al. 2019

Adv Funct Materials

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The crystal structures of the charge-transfer (CT) cocrystals formed by the π-electron acceptor 1,3,4,5,7,8-hexafluoro-11,11,12,12-tetracyanonaphtho-2,6-quinodimethane (F 6 TNAP) with the planar π-electron-donor molecules triphenylene (TP), benzo[b]benzo[4,5]thieno[2,3-d]thiophene (BTBT), benzo[1,2-b:4,5-b′]dithiophene (BDT), pyrene (PY), anthracene (ANT), and carbazole (CBZ) have been determined using single-crystal X-ray diffraction (SCXRD), along with those of two polymorphs of F 6 TNAP. All six cocrystals exhibit 1:1 donor/acceptor stoichiometry and adopt mixed-stacking motifs. Cocrystals based on BTBT and CBZ π-electron donor molecules exhibit brickwork packing, while the other four CT cocrystals show herringbone-type crystal packing. Infrared spectroscopy, molecular geometries determined by SCXRD, and electronic structure calculations indicate that the extent of ground-state CT in each cocrystal is small. Density functional theory calculations predict large conduction bandwidths and, consequently, low effective masses for electrons for all six CT cocrystals, while the TP-, BDT-, and PYbased cocrystals are also predicted to have large valence bandwidths and low effective masses for holes. Charge-carrier mobility values are obtained from space-charge limited current (SCLC) measurements and field-effect transistor measurements, with values exceeding 1 cm 2 V −1 s −1 being estimated from SCLC measurements for BTBT:F 6 TNAP and CBZ:F 6 TNAP cocrystals. exhibit properties distinct from those of their individual components. In chargetransfer (CT) cocrystals, one component acts as an π-electron donor (D) and another component acts as a π-electron acceptor (A), and both are typically planar molecules in order to facilitate CT interactions in the solid state. Two major types of molecular stacking motifs are found in CT crystals with 1:1 stoichiometry: mixed stacks, in which D and A molecules alternate along the stacking direction, -D-A-D-A, and segregated stacks, in which donor and acceptor molecules form separate stacks, -D-D-D-and -A-A-A. [1][2][3] When free of disorder, metallic conductivities can be obtained along the stacking direction of CT cocrystals that form segregated stacks and that exhibit extents of CT approximately midway (ρ = ca. 0.5) between the completely neutral (ρ = 0) and fully ionic (ρ = 1) limits. [1][2][3][4] On the other hand, CT cocrystals that consist of mixed stacks generally behave as semiconductors or insulators. [3,5] Recently there has been increasing interest in the semiconducting [6][7][8][9][10][11][12][13][14][15][16][17][18] and photoconductive [19][20][21] properties of mixed-stack cocrystals. Large charge-carrier mobility values, µ, have been reported for several examples using space-charge limited current (SCLC) or field-effect transistor (FET) measurements, includingThe ORCID identification number(s) for the author(s) of this article can be found under https://doi.

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“…Benzothiophene‐based compounds are good examples as the donor components. For example, dithieno[2,3‐ d ;2′3′‐ d ′]benzo[1,2‐b;4,5‐ b ′]dithiophene (DTBDT) can be assembled into mixed‐stack complexes with F n TCNQ or DMDCNQI by physical vapor transport [72] . For the single‐crystal‐based FET device with the polystyrene (PS) passivation layer and carbon paste as S/D electrodes, the as‐fabricated transistors displayed electron mobilities on the order of 0.1 cm 2 V −1 s −1 for DTBDT‐TCNQ and the order of 10 −3 cm 2 V −1 s −1 for DTBDT‐F 2 TCNQ, DTBDT‐F 4 TCNQ, and DTBDT‐DMDCNQI co‐crystals, respectively.…”

Section: Functionality Investigation Of Charge‐ Transfer Complexesmentioning

confidence: 99%

Multifunctional Features of Organic Charge‐Transfer Complexes: Advances and Perspectives

Wang

Luo

Peng

et al. 2020

Chemistry A European J

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The recent progress of charge‐transfer complexes (CTCs) for application in many fields, such as charge transport, light emission, nonlinear optics, photoelectric conversion, and external stimuli response, makes them promising candidates for practical utility in pharmaceuticals, electronics, photonics, luminescence, sensors, molecular electronics and so on. Multicomponent CTCs have been gradually designed and prepared as novel organic active semiconductors with ideal performance and stability compared to single components. In this review, we mainly focus on the recently reported development of various charge‐transfer complexes and their performance in field‐effect transistors, light‐emitting devices, lasers, sensors, and stimuli‐responsive behaviors.

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Carrier Charge Polarity in Mixed-Stack Charge-Transfer Crystals Containing Dithienobenzodithiophene

Cited by 35 publications

References 64 publications

Molecular Semiconductors for Logic Operations: Dead‐End or Bright Future?

Molecular Semiconductors for Logic Operations: Dead‐End or Bright Future?

Charge‐Transport Properties of F₆TNAP‐Based Charge‐Transfer Cocrystals

Multifunctional Features of Organic Charge‐Transfer Complexes: Advances and Perspectives

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Carrier Charge Polarity in Mixed-Stack Charge-Transfer Crystals Containing Dithienobenzodithiophene

Cited by 35 publications

References 64 publications

Molecular Semiconductors for Logic Operations: Dead‐End or Bright Future?

Molecular Semiconductors for Logic Operations: Dead‐End or Bright Future?

Charge‐Transport Properties of F6TNAP‐Based Charge‐Transfer Cocrystals

Multifunctional Features of Organic Charge‐Transfer Complexes: Advances and Perspectives

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Charge‐Transport Properties of F₆TNAP‐Based Charge‐Transfer Cocrystals