Oxadiazole-integrated heterocoronene discotics as ambipolar organic semiconductors

De, Ritobrata; De, Joydip; Gupta, Santosh Prasad; Bala, Indu; Ankita, .; Tarun, .; Pandey, Upendra Kumar; Pal, Santanu Kumar

doi:10.1039/d2tc04144h

Cited by 10 publications

(6 citation statements)

References 39 publications

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“…21 The charge transport properties of the materials were studied via space charge limited current (SCLC) method in solution-processed thin films (all of the experimental details are given in the SI). 20,43 According to the HOMO energy level of the materials (E HOMO ≈ −5.13 eV), Au was selected as injecting electrode (W Au ≈ −5.1 eV) in order to get an effective ohmic contact. Indium Tin Oxide (ITO) was selected as counter electrode due to its work function (W ITO ≈ −4.7 eV), which is considerably lower than the LUMO energy level of the materials (E LUMO ≈ −2.62) eV.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…In order to obtain efficient devices with high charge mobility values and to establish a structure–property correlation, a large number of molecular architectures have been reported in recent years. Among them, planar cores such as triphenylene, − perylene, ,, or coronene − are the most prominent due to their high propensity to form efficient stacks. In contrast, nonplanar propeller-shaped molecules, such as triphenylamine (TPA), with an exceptional electron-donating character, have been much less used in the design of semiconductor CLC.…”

Section: Introductionmentioning

confidence: 99%

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Effect of Hydrogen Bonding and Chirality in Star-Shaped Molecules with Peripheral Triphenylamines: Liquid Crystal Semiconductors and Gels

Martínez-Bueno,

Martín,

Ortega

et al. 2024

Chem. Mater.

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Organic semiconductors with well-defined architectures pose a suitable alternative to amorphous silicon-based inorganic semiconductors. Encouraged by the development of organic semiconductors based on columnar liquid crystals, herein, we report on a family of C 3 -symmetric star-shaped mesogens based on triphenylamine (TPA), a functional unit with strong electron donor character. Highly stable columnar phases with high hole mobility values were obtained out of this nonplanar functional unit, and this was achieved by using flexible amide spacers to join the TPA units to a tris(triazolyl)triazine (T) star-shaped core, allowing the formation of intermolecular hydrogen bonds. The presence of hydrogen bonds results in a stabilization of the columnar architectures either in bulk or in the presence of solvents by reinforcing π-stacking and van der Waals interactions, as deduced by Fourier-transform infrared (FTIR) and X-ray diffraction (XRD) studies. Furthermore, the introduction of a stereogenic center in the flexible spacer prompts the formation of chiral aggregates in the liquid crystal state and in the organogel formed in 1-octanol, as demonstrated by circular dichroism spectroscopy.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Effect of Hydrogen Bonding and Chirality in Star-Shaped Molecules with Peripheral Triphenylamines: Liquid Crystal Semiconductors and Gels

Martínez-Bueno,

Martín,

Ortega

et al. 2024

Chem. Mater.

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“…This higher voltage region is characteristic of the SCLC regime and here, the current is known to directly depend on charge mobility . The J – V curves for both compounds 3a and 5a were later fitted to the Mott–Gurney equation given below, where J is the current density, ε 0 is the permittivity of free space, ε is the dielectric constant of the DLC compounds, μ is the electron or hole mobility, V is the voltage drop across the device, and L is the thickness of the sample , …”

Section: Resultsmentioning

confidence: 99%

Exploring the Ambipolar Charge Carrier Mobility, Mesomorphic, and Gel Properties in Nitrile Extended Quinoxaline and Phenanthro[a]phenazine Discotic Liquid Crystals

Patra,

Behera,

Shah

et al. 2024

ACS Appl. Electron. Mater.

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A set of cyano-substituted dibenzo-quinoxaline and phenanthro-phenazine discotic mesomorphs have been synthesized, and the impact of ring closure on thermal, optical, electronic, and physical properties has been investigated. Although dibenzoquinoxaline shows incredible fluorescence and a low-temperature mesophase, a straightforward ring closure has decreased the molecular distortion in the case of phenanthro-phenazine, thereby resulting in a more stable arrangement. A robust columnar hexagonal self-assembly in the phenanthro[a]phenazine compound facilitates a hole mobility of 1.02 × 10 −2 cm 2 V −1 s −1 , which is 100-fold more than that of the dibenzo quinoxaline analogue. This demonstrates the tunability in self-assembly as well as the physical and electronic properties of discotic liquid crystalline materials with a simple modification in the chemical structure. A study of their gelation properties has also been explored, and models of the organization of molecules within the individual fiber in the gel network have been proposed in agreement with X-ray diffraction studies. These two sets of low band gap ambipolar materials have significant potential to be used in the fabrication of various optoelectronic devices.

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“…9). 109 The resulting Het-OXD DLCs showed a room-temperature Col h mesophase that persisted even up to a temperature of 260 °C. This demonstrated the ability of the oxadiazole units to stabilize the columnar architecture over wide temperature ranges by averting disorder in the assembly.…”

Section: Exploring Different Cores Self-assemblies and Techniquesmentioning

confidence: 96%

Self-assembled discotics as molecular semiconductors

Pal

2023

Chem. Commun.

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Oxadiazole-integrated heterocoronene discotics as ambipolar organic semiconductors

Abstract: Development in modern technologies has enforced a quest for new semiconducting materials in optoelectronics where self-assembled liquid crystalline (LCs) materials can play a potential role. Molecular engineering of disc-shaped LCs...

Cited by 10 publications

References 39 publications

Effect of Hydrogen Bonding and Chirality in Star-Shaped Molecules with Peripheral Triphenylamines: Liquid Crystal Semiconductors and Gels

Effect of Hydrogen Bonding and Chirality in Star-Shaped Molecules with Peripheral Triphenylamines: Liquid Crystal Semiconductors and Gels

Exploring the Ambipolar Charge Carrier Mobility, Mesomorphic, and Gel Properties in Nitrile Extended Quinoxaline and Phenanthro[a]phenazine Discotic Liquid Crystals

Self-assembled discotics as molecular semiconductors

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