Single photon triggered dianion formation in TCNQ and F4TCNQ crystals

Ma, Lin; Hu, Peng; Jiang, Hui; Kloc, Christian; Sun, Handong; Soci, Cesare; Voityuk, Alexander A.; Michel‐Beyerle, M. E.; Gurzadyan, Gagik G.

doi:10.1038/srep28510

Cited by 39 publications

(48 citation statements)

References 30 publications

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“…The new absorption band could be attributed to either F 4 ‐TCNQ anion as a result of integer charge transfer, or C 8 ‐BTBT/ F 4 ‐TCNQ complex due to partial charge transfer, which are the two primary molecular doping mechanisms reported so far . The F 4 ‐TCNQ anions have been previously reported to exhibit sharp absorption peaks at around 767 and 869 nm . Given the absence of these absorption features in our case, we attribute the appearance of the broad absorption band to the formation of the C 8 ‐BTBT/ F 4 ‐TCNQ charge transfer complex (CPX).…”

supporting

confidence: 47%

Large Modulation of Charge Carrier Mobility in Doped Nanoporous Organic Transistors

et al. 2017

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Molecular doping of organic electronics has shown promise to sensitively modulate important device metrics. One critical challenge is the disruption of structure order upon doping of highly crystalline organic semiconductors, which significantly reduces the charge carrier mobility. This paper demonstrates a new method to achieve large modulation of charge carrier mobility via channel doping without disrupting the molecular ordering. Central to the method is the introduction of nanopores into the organic semiconductor thin films via a simple and robust templated meniscus-guided coating method. Using this method, the charge carrier mobility of C -benzothieno[3,2-b]benzothiophene transistors is boosted by almost sevenfold. This paper further demonstrates enhanced electron transport by close to an order of magnitude in a diketopyrrolopyrrole-based donor-acceptor polymer. Combining spectroscopic measurements, density functional theory calculations, and electrical characterizations, the doping mechanism is identified as partial-charge-transfer induced trap filling. The nanopores serve to enhance the dopant/organic semiconductor charge transfer reaction by exposing the π-electrons to the pore wall.

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supporting

confidence: 47%

Large Modulation of Charge Carrier Mobility in Doped Nanoporous Organic Transistors

et al. 2017

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“…We assign the signal at 2162 and 2132 cm −1 to the F4TCNQ −1 anions and F4TCNQ −2 dianions, respectively. Dianions have been observed previously . From the shift in vibrational energy, the degree of charge transfer (δ) can be quantified according to

δ = \frac{2 Δ υ}{υ_{0}} {([], 1 normal - normal \frac{υ_{1}^{2}}{υ_{0}^{2}})}^{- 1}

where υ 0 = 2192 cm −1 and υ 1 = 2162 cm −1 are the wavenumbers recorded for neat (dissolved) F4TCNQ and the anion, respectively, and Δυ = υ 1 −υ 0 .…”

mentioning

confidence: 99%

Polar Side Chains Enhance Processability, Electrical Conductivity, and Thermal Stability of a Molecularly p‐Doped Polythiophene

et al. 2017

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Molecular doping of organic semiconductors is critical for optimizing a range of optoelectronic devices such as field‐effect transistors, solar cells, and thermoelectric generators. However, many dopant:polymer pairs suffer from poor solubility in common organic solvents, which leads to a suboptimal solid‐state nanostructure and hence low electrical conductivity. A further drawback is the poor thermal stability through sublimation of the dopant. The use of oligo ethylene glycol side chains is demonstrated to significantly improve the processability of the conjugated polymer p(g42T‐T)—a polythiophene—in polar aprotic solvents, which facilitates coprocessing of dopant:polymer pairs from the same solution at room temperature. The use of common molecular dopants such as 2,3,5,6‐tetrafluoro‐7,7,8,8‐tetracyanoquinodimethane (F4TCNQ) and 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone (DDQ) is explored. Doping of p(g42T‐T) with F4TCNQ results in an electrical conductivity of up to 100 S cm−1. Moreover, the increased compatibility of the polar dopant F4TCNQ with the oligo ethylene glycol functionalized polythiophene results in a high degree of thermal stability at up to 150 °C.

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“…F4TCNQ has a deep LUMO level of À5.24 eV, 55 which is energetically lower than the HOMO level of PEDOT (À4.87 eV). 53 F4TCNQ solution of 1 mg/mL in the mixture of dichloromethane (DCM) and tetrahydrofuran (THF) (1:4 by volume), a pale yellow solution, was spin-coated onto PEDOT at 3000 r/min.…”

Section: Resultsmentioning

confidence: 99%

“…And then the color of the film changed to ultra-light green, which was the color of F4TCNQ anions according to the literature. 55 The thickness of the F4TCNQ layer was calculated by the difference of the thicknesses of PEDOT and the dipolar film, which was under 4 nm. Since it was small and not precise, we used the thickness of PEDOT to represent the dipolar film.…”

Section: Resultsmentioning

confidence: 99%

“…52 Herein, the neutral PEDOT thin film was deposited on an ITO electrode by in situ ECP through the cyclic voltammetry (CV) method, and then a F4TCNQ thin layer was spin-coated atop the PEDOT layer. Because the LUMO of F4TCNQ is lower than the HOMO of PEDOT, [53][54][55] the spontaneous electron transfer from PEDOT to F4TCNQ results in a bilayer structure of PEDOT cations and F4TCNQ anions. Thus, a permanent interfacial dipole is formed in the surface-doping system.…”

Section: Introductionmentioning

confidence: 99%

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Construction of Interface Dipoles by Surface Doping and Their Role in the Open Circuit Voltage in Polymer Solar Cells

Wen

Zhou

et al. 2020

Organic Materials

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A kind of dipolar interface is realized by surface doping of poly-(3,4-ethylenedioxythiophene) (PEDOT) with tetrafluoro-tetracyano-quinodimethane (F4TCNQ). PEDOT is in situ synthesized by electrochemical polymerization of 3,4-ethylenedioxythiophene (EDOT) on an indium tin oxide (ITO) electrode, and then F4TCNQ is spin-coated atop the PEDOT layer. Because the LUMO of F4TCNQ is lower than the HOMO of PEDOT, the spontaneous electron transfer from PEDOT to F4TCNQ results in a bilayered structure of PEDOT cations and F4TCNQ anions. Thus, a permanent interfacial dipole is formed in the surface-doping system. The surface doping not only enhances the conductivity of PEDOT, but also increases the surface work function of the electrode. The dipolar film is applied as the anode interface in polymer solar cells (PSCs), and the results show that such an interface dipole plays a very important role in the open circuit voltage (V oc) of the PSCs.

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Single photon triggered dianion formation in TCNQ and F4TCNQ crystals

Cited by 39 publications

References 30 publications

Large Modulation of Charge Carrier Mobility in Doped Nanoporous Organic Transistors

Large Modulation of Charge Carrier Mobility in Doped Nanoporous Organic Transistors

Polar Side Chains Enhance Processability, Electrical Conductivity, and Thermal Stability of a Molecularly p‐Doped Polythiophene

Construction of Interface Dipoles by Surface Doping and Their Role in the Open Circuit Voltage in Polymer Solar Cells

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