Synthesis of Linearly Fused Benzodipyrrole Based Organic Materials

Vlasselaer, Maarten; Dehaen, Wim

doi:10.3390/molecules21060785

Cited by 34 publications

(14 citation statements)

References 111 publications

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“…Among the different synthetic routes (Vlasselaer & Dehaen, 2016), the twofold Cadogan reaction (Cadogan et al, 1965) is a very successful route to indolocarbazoles (Kistenmacher & Mü llen, 1992;Wrobel et al, 2013) and is also suitable for the preparation of higher oligomers (Srour et al, 2016). In a continuation of our studies on indolo-annulated heterocycles (Dassonneville et al, 2011;Nissen & Detert, 2011;Letessier & Detert, 2013), we present here the first X-ray structure of a linear diindolocarbazole (Fig.…”

Section: Structure Descriptionmentioning

confidence: 99%

1,4,9,12-Tetramethoxy-14-octyl-5,8-dihydrodiindolo[3,2-b;2′,3′-h]carbazole with an unknown solvent

et al. 2017

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The title compound, 2C36H39N3O4·H2O, is a linear π-conjugated ladder oligomer with an alkyl chain on the central nitrogen atom. This diindolocarbazole, preparedviaa twofold Cadogan reaction, adopts a sligthly convex shape,antito the disordered octyl group. The unit cell contains nine molecules of the title compound and half a water molecule per main molecule. The water molecule forms hydrogen bridges, connecting the carbazole-NH and methoxy groups of different molecules. The crystal contains solvent molecules which are located in a channel parallel to thecaxis. It was not possible to determine the position and nature of the solvent (a mixure of choroform,n-pentane and DMSO). The SQUEEZE [Spek (2015).Acta Cryst.C71, 9–18] option ofPLATONwas used to model the missing electron density. The given chemical formula and other crystal data do not take into account these solvent molecules.

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Section: Structure Descriptionmentioning

confidence: 99%

1,4,9,12-Tetramethoxy-14-octyl-5,8-dihydrodiindolo[3,2-b;2′,3′-h]carbazole with an unknown solvent

et al. 2017

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“…Although other possible configurations also exist, these are rather rare and usually not incorporated in the “classical” indolocarbazole concept [36] . In particular, the chemistry of indolo[3,2‐ b ]carbazole has frequently been reported in the literature, [37–41] evidencing a quinoidal character for its ground state [42, 43] and an easy modulation of their properties by the insertion of functional groups [44–48] . However, the introduction of dicyanomethylene terminal groups, a well‐known strategy to stabilize diradical species, has not been explored so far in these materials.…”

Section: Introductionmentioning

confidence: 99%

Dynamic Covalent Properties of a Novel Indolo[3,2‐b]carbazole Diradical

Badía-Domínguez

Peña-Álvarez

Wang

et al. 2021

Chemistry A European J

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This work describes the synthesis and properties of ad icyanomethylene-substituted indolo[3,2-b]carbazole diradical ICz-CN. This quinoidal system dimerises almost completely to (ICz-CN) 2 ,w hich contains two long C(sp 3)À C(sp 3) s-bonds between the dicyanomethylene units. The minor open-shell ICz-CN component in the solid-state mixture was identified by EPR spectroscopy.C yclic voltammetry and UV-visible spectroelectrochemical data, as well as comparison with reference monomerI Cz-Br reveal that the nature of the one-electrono xidation of (ICz-CN) 2 at ambient temperature and ICz-CN at elevated temperature is very similar in all these compounds due to the prevailing localization of their HOMO on the ICz backbone. The peculiar cathodic behaviour reflects the coexistence of (ICz-CN) 2 and ICz-CN. The involvement of the dicyanomethylene groupss tabilizes the close-lying LUMO and LUMO + 1o f(ICz-CN) 2 and especially ICz-CN comparedt oI Cz-Br,r esulting in ad istinctive cathodic response at low overpotentials. Differently from neutralI Cz-CN, its radicala nion and dianion are remarkably stable under ambient conditions. The UV/Vis(-NIR) electronic transitions in parent (ICz-CN) 2 and ICz-CN and their different redox forms have been assigned convincingly with the aid of TD-DFT calculations. The s-bond in neutral(ICz-CN) 2 is cleaved in solution and in the solid-state upon soft external stimuli (temperature, pressure), showing as trong chromism from light yellow to blue-green. Notably,i nt he solid state, the monomeric diradical species is predominantly formed under high hydrostatic pressure (> 1GPa).

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“…Small‐molecule organic semiconductors are of interest for a variety of electronic devices, including organic thin‐film transistors (TFTs) [1] . Among the large number of molecular motifs that have been explored for the fabrication of organic p‐channel TFTs are the indolocarbazoles (ICZs) [2,3] . Indolocarbazoles are typically characterized by good solubility in common organic solvents and good air stability, which can be attributed to their low‐lying HOMO‐energy level.…”

Section: Introductionmentioning

confidence: 99%

Gold Catalysis Meets Materials Science – A New Approach to π‐Extended Indolocarbazoles

et al. 2020

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Herein we describe a modular, convergent synthesis of substituted benzo[a]benzo[6,7]‐indolo[2,3‐h]carbazoles (BBICZs) using a bidirectional gold‐catalyzed cyclization reaction as a key step. A building block strategy enabled the easy variation of substituents at different positions of the core structure and a general analysis of substitution effects on the materials properties of the target compounds. All BBICZs were fully characterized and their optical and electronic properties were studied experimentally as well as by computational methods. Organic thin‐film transistors based on eight selected derivatives were fabricated by vacuum deposition and charge‐carrier mobilities up to 1 cm2/Vs were measured.

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Synthesis of Linearly Fused Benzodipyrrole Based Organic Materials

Cited by 34 publications

References 111 publications

1,4,9,12-Tetramethoxy-14-octyl-5,8-dihydrodiindolo[3,2-b;2′,3′-h]carbazole with an unknown solvent

1,4,9,12-Tetramethoxy-14-octyl-5,8-dihydrodiindolo[3,2-b;2′,3′-h]carbazole with an unknown solvent

Dynamic Covalent Properties of a Novel Indolo[3,2‐b]carbazole Diradical

Gold Catalysis Meets Materials Science – A New Approach to π‐Extended Indolocarbazoles

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