Isomeric carbazolocarbazoles: synthesis, characterization and comparative study in Organic Field Effect Transistors

Más‐Montoya, Miriam; Ortiz, Rocío Ponce; Curiel, David; Espinosa, Arturo; Allain, Magali; Facchetti, Antonio; Marks, Tobin J.

doi:10.1039/c2tc00363e

Cited by 39 publications

(31 citation statements)

References 58 publications

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“…In addition, the smoother surface morphology also generally improves the contact between the top electrode and the active layer, thereby reducing the contact resistance. 41 Both of these changes help to improve the ternary device yield and lower the switching voltages.…”

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confidence: 99%

Surface engineering to achieve organic ternary memory with a high device yield and improved performance

et al. 2017

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confidence: 99%

Surface engineering to achieve organic ternary memory with a high device yield and improved performance

et al. 2017

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“…For example, Mas‐Montoya et al. reported a series of π‐expanded hexacyclic carbazolocarbazoles (CBZCBZ) isomers that show hole mobilities in the range of 10 −6 −10 −2 cm 2 V −1 s −1 2f. In addition, challenges in synthesis and solubility also emerge with the π‐expansion of N‐heteroacenes 2e.…”

Section: Methodsmentioning

confidence: 99%

“…In addition, challenges in synthesis and solubility also emerge with the π‐expansion of N‐heteroacenes 2e. f, 5 Thus, new strategies should be explored to improve the performance of carbazole‐based N‐heteroacenes.…”

Section: Methodsmentioning

confidence: 99%

Carbazolo[2,1‐a]carbazole Diimide: A Building Block for Organic Electronic Materials

et al. 2014

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A new class of carbazolo[2,1‐a]carbazole diimide compounds (CBZCBZ‐DI, 3) are designed and synthesized. The synthesis, X‐ray crystal structure, absorption spectra, and electrochemical properties of 3 as well as the charge transport properties are investigated. Theoretical calculation is also carried out based on the X‐ray crystal structure of 3 a to understand the relationship between the structure and the charge transport properties. Single‐crystal X‐ray analysis revealed that the molecules of 3 a adopt a slipped face‐to‐face π‐stacking mode with a large intermolecular π‐overlap and an interplanar distance of 3.4 Å. Crystalline transistors of 3 a display high hole mobility of 0.5 cm2 V−1 s−1, which is among the highest reported mobility values for carbazole‐based N‐heteroacenes. Two useful brominated derivatives (4, 5) are also prepared for synthesizing more new π‐functional materials.

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“…For example, isomers of carbazolo[1,2‐ a ]carbazoles and carbazolo[3,2‐ b ]carbazoles have different packing patterns. Compared to [1,2‐ a ]carbazole derivatives, [3,2‐ b ] carbazole derivatives have a higher mobility in air with a highly ordered molecular arrangement in the sublimed films . Another example is that the difference of the 6,6′‐ and 5,5′‐benzene substituent position on the isoindigo core was investigated in organic solar cells, and the results showed that the 6,6′‐substituent exhibited a stronger intramolecular charge‐transfer band owing to strong electronic coupling between the 6,6′‐substituent and the core .…”

Section: Introductionmentioning

confidence: 99%

Altering the Position of Phenyl Substitution to Adjust Film Morphology and Memory Device Performance

Zhou

et al. 2015

Chemistry An Asian Journal

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In this study, two structural isomers α-PBT and β-PBT, which only differ in the phenyl substituent position on the quinoline chromophore, have been designed and successfully synthesized. The influences of substituent position on the film morphology and the storage performance of the devices were investigated. Both molecules employed in the memory devices exhibited same nonvolatile binary (write-once-read-many-times; WORM) characteristics, but the switch threshold voltage (Vth) of the β-PBT-based device was clearly lower than that of the α-PBT-based device. Simulation results demonstrate that the variation of the phenyl substituent position led to different intermolecular stacking styles and thus to varied grain sizes for each film morphology. This work illustrates that altering the phenyl substituent position on the molecular backbone could improve the quality of the film morphology and reduce power consumption, which is good for the rational design of future advanced organic memory devices (OMDs).

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Isomeric carbazolocarbazoles: synthesis, characterization and comparative study in Organic Field Effect Transistors

Cited by 39 publications

References 58 publications

Surface engineering to achieve organic ternary memory with a high device yield and improved performance

Surface engineering to achieve organic ternary memory with a high device yield and improved performance

Carbazolo[2,1‐a]carbazole Diimide: A Building Block for Organic Electronic Materials

Altering the Position of Phenyl Substitution to Adjust Film Morphology and Memory Device Performance

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