Insight into the Diindolo[3,2-b:2′,3′-h]carbazole Core as an Air-Stable Semiconductor for OTFTs

Abstract

Encouraged by the outstanding performance of pentacene, the perspective over enhanced organic semiconductors has been focused on studying analogous ladder-type materials. In this context, the case of the diindolo­[3,2-b:2′,3′-h]­carbazole core is a promising example of a semiconductor with improved stability. Herein, we report the synthesis of five diindolo­[3,2-b:2′,3′-h]­carbazole derivatives displaying different alkylation patterning, as well as their integration in organic thin-film transistors. The elucidation of the single-crystal structures of three of the derivatives, accomplished by means of powder X-ray diffraction (PXRD), provided further insight into the intermolecular disposition of this core. As a result, the relationship between the structural design and the performance of the final devices could be analyzed. Globally, a scope of mobility values from 10–6 to 10–3 cm2 V–1 s–1 was achieved by just fine-tuning the length of the alkyl chains and the type of passivation layer applied onto the SiO2 surface. Remarkably, all the fabricated devices excel in terms of temporal and air stability with a shelf lifetime up to years, a coveted feature in organic electronics that confirms the potential of this core.

Enhancement of Blue Doping-Free and Hyperfluorescent Organic Light Emitting Diode Performance through Triplet–Triplet Annihilation in the Derivatives of Anthracene and Carbazole

“…Absorption spectra of toluene solutions of the compounds (Figure a) consist of the signature absorption peaks of carbazole at a wavelength shorter than 350 nm and vibronic multipeak bands of anthracene in the longer wavelength range. , The carbazole-related absorption band of the low-energy π–π* transition around 300 nm is bathochromically shifted for An-MCz and An-ECz when compared to that for An-tBCz due to the attachments of alkoxy substituents to the carbazole moieties notably increasing π-conjugation . The anthracene-based vibronic bands are located almost at identical wavelengths for all the investigated compounds.…”

Preparation of Carbazoles Involving 6π‐Electrocyclization, Photoredox‐, Electrochemical‐, and Thermal Cyclization Reactions: Mechanistic Insights

“…The synthetic approach to diindolo[3,2‐ b :2’,3’‐ h ]carbazole core which is a promising example of a semiconductor with improved stability was based on a twofold Cadogan ring closure promoted by microwave irradiation on 3,6‐dinitrocarbazole derivatives and the cyclized products thus obtained were alkylated providing the desired final products in very modest yields [65] …”

Programming Positive Mechanofluorescence in Liquid Crystalline Elastomers

“…Carbazole is a recurrent and highly versatile scaffold within chemistry, biomedicine, and materials science because of its attractive luminescent and semiconductor properties, which can be fine-tuned through not only the subtle and rational modification of its molecular structure but also imparting control over the interactions established with the environment at the supramolecular level. − …”