Details

Autor(en) / Beteiligte

• Jebnouni, Achref
• Teka, Safa
• Heinrich, Benoit
• Majdoub, Mustapha
• Jaballah, Nejmeddine Smida
• Leclerc, Nicolas

Titel

Molecular semiconductors with Carbazole versus Triazatruxene endcaps: A matter of self-assembly

Ist Teil von

• Journal of molecular structure, 2024-12, Vol.1318, p.139241, Article 139241

Ort / Verlag

Elsevier B.V

Erscheinungsjahr

2024

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• •Novel carbazole and diketopyrrolopyrrole-based molecule (CAR-TzDPP) was synthesized.•A comparative study between the carbazole and triazatruxene endcaps was conducted.•Experimental and theoretical properties (DFT and TD-DFT) were found in good agreement.•Two-dimensional (2D) ambipolar charge transport was observed in CAR-TzDPP thin film.•Triazatruxene-based molecule (TAT-TzDPP) provides 3D unipolar charge transport. In this work, we describe the design and synthesis of a novel soluble conjugated molecule, CAR-TzDPP, consisting of a central diketopyrrolopyrrole core (DPP) connected to carbazole endcaps through thiazole rings. To evaluate its properties, a triazatruxene-based molecule (TAT-TzDPP) was used as a model for comparison. The electrochemical and the in-solution optical properties are in good agreement with those obtained from DFT calculations. However, the thin-film self-assemblies of CAR-TzDPP exhibited distinct differences, forming a more standard crystalline structure including insulating side-chains layers that disallowed side interactions between aromatic rings. This resulted in a reduced charge transport ability to a two-dimensional (2D) ambipolar charge transport in CAR-TzDPP, compared to the nearly isotropic unipolar charge transport in TAT-TzDPP. Despite this, CAR-TzDPP can be considered a viable alternative for device configurations requiring semiconducting pathways aligned in the substrate plane due to its simplified and high yield synthesis route, ease of processing, and reliable charge mobility in OFETs. This research highlights the significance of molecular units in small semiconducting organic molecules, not only in terms of their individual optoelectronic properties but also in terms of their self-assembly capabilities, which ultimately influence their charge transport properties. [Display omitted]