Heterocyclic heptacene analogs – 8H-16,17-epoxydinaphto[2,3-c:2′,3′-g]carbazoles as charge transport materials

Rimkus, Renaldas; Tumkevičius, Sigitas; Serevičius, Tomas; Komskis, Regimantas; Adomenas, P. V.; Gruodis, Alytis; Jankauskas, Vygintas; Kazlauskas, Karolis; Juršėnas, Saulius

doi:10.1016/j.dyepig.2015.08.029

Cited by 10 publications

(6 citation statements)

References 46 publications

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“… a Reagents and conditions: (a) Pd(OAc) 2 , dppm, CsO 2 CCMe 3 , DMF, 110 °C; (b) Pd(OAc) 2 , Cs 2 CO 3 , TBAB, DMF, 100 °C, 2 h; (c) Cu, Cs 2 CO 3 , pyridine, 150 °C, 24 h; (d) photochemical, benzene; (e) NaOH, dioxane/EtOH/water, reflux, 30 min; (f) Cu bronze diethyl phthalate, 94% as picrate; (g) PCl 3 , 1,2-DCE, 80 °C, 12 h. …”

Section: Nonbenzenoid Fusionmentioning

confidence: 99%

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

et al. 2016

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Two-dimensionally extended, polycyclic heteroaromatic molecules (heterocyclic nanographenes) are a highly versatile class of organic materials, applicable as functional chromophores and organic semiconductors. In this Review, we discuss the rich chemistry of large heteroaromatics, focusing on their synthesis, electronic properties, and applications in materials science. This Review summarizes the historical development and current state of the art in this rapidly expanding field of research, which has become one of the key exploration areas of modern heterocyclic chemistry.

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Section: Nonbenzenoid Fusionmentioning

confidence: 99%

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

et al. 2016

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“…Compounds 7 , 8 , 9 , 10 , 11 , 12 , and 13 were synthesized according to previously reported procedures. Carbazole trimers 1 – 6 were obtained in modest‐to‐good yields from Pd/Cu‐catalyzed Sonogashira cross‐coupling reactions between terminal alkynes 7 , 9 , and 12 and dihalides 8 , 10 , 11 , and 13 , as shown in Scheme .…”

Section: Resultsmentioning

confidence: 99%

“…3‐Ethynyl‐9‐hexyl‐9 H ‐carbazole ( 7 ) and 9‐hexyl‐3,6‐diiodo‐9 H ‐carbazole ( 8 ) were prepared from 9‐hexyl‐9 H ‐carbazole according to the corresponding literature procedure. 3,6‐di‐ tert ‐Butyl‐9‐ethyl‐1‐ethynyl‐9 H ‐carbazole ( 9 ), 9‐ethyl‐3,6‐diiodo‐9 H ‐carbazole ( 10 ), and 3,6‐di‐ tert ‐butyl‐9‐ethyl‐1,8‐diiodo‐9 H ‐carbazole ( 11 ) were prepared from commercially available 9 H ‐carbazoles according to the corresponding literature procedure. 9‐Ethyl‐3‐ethynyl‐9 H ‐carbazole ( 12 ) was prepared from 9‐ethyl‐9 H ‐carbazole according to a literature procedure.…”

Section: Methodsmentioning

confidence: 99%

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Ethynylene‐Bridged Conjugate Carbazole Trimers: Synthesis and their Structural, Photophysical, and Electrochemical Properties

et al. 2017

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A series of six new ethynylene‐bridged conjugate carbazole trimers (1–6) were synthesized through sequential Pd‐catalyzed Sonogashira cross‐coupling reactions. The structural properties of these trimers were examined by using DFT calculations. Compound 6, in which the two terminal carbazole moieties were substituted at the 1‐position, exhibited the longest‐wavelength UV/Vis absorption maximum in CH2Cl2, whereas compound 1, in which the two terminal carbazole moieties were substituted at the 3‐position, exhibited the shortest‐wavelength absorption maximum. These trends were rationalized by using TDDFT calculations. Electrochemical measurements and DFT calculations revealed that trimers 1–6 had smaller HOMO–LUMO gaps compared with that for the corresponding monomer (14), which was caused by a lowering of the LUMO levels, rather than by a raising of the HOMO levels. Trimers 2–6 exhibited excellent emission properties with high fluorescence quantum yields, which were derived from their rigid structures.

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“…8), similarly to one of the recent V--shaped π--extended carbazoles. 41 The experimental data shown on For the calculation of the hole mobility of 3 the following equation was used: μ=d 2 /U·•t tr , where d is thickness of the film (1.5 μm), t tr is the transit time, and U is the applied voltage. The transit times were determined from the intersection of the asymptotes to the plateau and tail of the transient signal in the double logarithmic plots.…”

Section: Homo Lumomentioning

confidence: 99%

Nine-ring angular fused biscarbazoloanthracene displaying a solid state based excimer emission suitable for OLED application

et al. 2016

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A new biscarbazoloanthracene consisting of nine fused aromatic rings, including two pyrrole units, has been obtained in a straightforward and convergent synthesis. Computational chemistry and conformational analysis revealed that the semiconductor's molecule is not planar, the two carbazole moieties being helical twisted from the plane of the anthracene unit. Photophysical and electrochemical measurements showed that this angular fused heteroacene has a low lying HOMO energy level with a wide band gap despite its extended π--conjugated molecular framework. Based on its relatively low--lying HOMO level, the titled compound semiconductor promises a high environmental stability in comparison to other related linear fused acenes and heteroacenes. The biscarbazoloanthracene has been applied as the light emitting layer in a white light emitting diode (WOLED). It is proposed that the white OLED feature is due to dual light emission properties from the active semiconductor layer being based on both the molecular luminescence of the small molecule and a discrete excimer emission made possible by suitable aggregates in the solid state. Noteworthy, this is the first reported example of such a behavior observed in a small molecule heteroacene rather than an oligomer or a polymer.

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Heterocyclic heptacene analogs – 8H-16,17-epoxydinaphto[2,3-c:2′,3′-g]carbazoles as charge transport materials

Cited by 10 publications

References 46 publications

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

Ethynylene‐Bridged Conjugate Carbazole Trimers: Synthesis and their Structural, Photophysical, and Electrochemical Properties

Nine-ring angular fused biscarbazoloanthracene displaying a solid state based excimer emission suitable for OLED application

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