Polycarbazoles: 25 Years of Progress

Morin, Jean‐François; Leclerc, Mario; Adès, D.; Siove, Alain

doi:10.1002/marc.200500096

Cited by 615 publications

(379 citation statements)

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“…Polymers containing carbazole moiety are very promising new materials [3] and are widely used in electronics and photonics [4][5][6][7]. Due to their interesting properties, the chemistry of carbazole derivatives has been studied at length [8][9][10].…”

Section: Introductionmentioning

confidence: 99%

Molecular modeling and experimental studies on structure and NMR parameters of 9-benzyl-3,6-diiodo-9H-carbazole

et al. 2015

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A combined experimental and theoretical study has been performed on 9-benzyl-3,6-diiodo-9H-carbazole. Experimental X-ray (100.0 K) and room-temperature 13 C nuclear magnetic resonance (NMR) studies were supported by advanced density functional theory calculations. The non-relativistic structure optimization was performed and the 13 C nuclear magnetic shieldings were predicted at the relativistic level of theory using the zeroth-order regular approximation. The changes in the benzene and pyrrole rings compared to the unsubstituted carbazole or the parent molecules were discussed in terms of aromaticity changes using the harmonic oscillator model of aromaticity and the nucleus independent chemical shift indexes. Theoretical relativistic calculations of chemical shifts of carbons C3 and C6, directly bonded to iodine atoms, produced a reasonable agreement with experiment (initial deviation from experiment of 41.57 dropped to 5.6 ppm). A good linear correlation between experimental and theoretically predicted structural and NMR parameters was observed. Graphical AbstractKeywords 9-Benzyl-3,6-diiodo-9H-carbazole Á X-ray structure Á 13 C NMR spectra Á ZORA Á GIAO NMR calculations Á HOMA Á NICS

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Section: Introductionmentioning

confidence: 99%

Molecular modeling and experimental studies on structure and NMR parameters of 9-benzyl-3,6-diiodo-9H-carbazole

et al. 2015

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“…Poly(2,7-carbazole) derivatives (PCzs) 5 represent another class of bridged phenylene-based polymers (Morin et al 2005; scheme 2). Owing to the substituted nitrogen in the polycyclic system, formation of oxidation defects is excluded, which led to stable materials with good solubility, high processability and optical properties covering the blue, green and red ranges (Morin & Leclerc 2002).…”

Section: Conjugated Polymersmentioning

confidence: 99%

Expanding benzene to giant graphenes: towards molecular devices

Müller

Müllen

2007

Phil. Trans. R. Soc. A.

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Phenylene-based conjugated materials provide versatile platforms for the development of molecular devices. Architectures of one-and two-dimensional polyphenylenes, which self-assemble into three-dimensional objects with advantageous electronic properties, have been investigated. Systematic relations between the size, substitution and shape with function were found, which enabled the further optimization of the materials. Hand in hand with the development of suitable methods for visualization and processing, promising results were obtained for performance of nanoscale electronic devices.

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“…Indeed, these materials have been widely used in optoelectronics [13] and particularly as emitters in OLEDs by several of us [14][15][16][17]. The main goal of our work is turned towards synthetic chemistry of luminescent organic materials belonging to the carbazole family.…”

Section: __________________ * Corresponding Authormentioning

confidence: 99%

Doped and non-doped organic light-emitting diodes based on a yellow carbazole emitter into a blue-emitting matrix

et al. 2007

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A new carbazole derivative with a 3,3'-bicarbazyl core 6,6'-substituted by dicyanovinylene groups (6,6'-bis(1-(2,2'-dicyano)vinyl)-N,N'-dioctyl-3,3'-bicarbazyl; named (OcCz2CN) 2 , was synthesized by carbonyl-methylene Knovenagel condensation, characterized and used as a component of multilayer organic light-emitting diodes (OLEDs). Due to its π-donor-acceptor type structure, (OcCz2CN) 2 was found to emit a yellow light at λ max =590 nm (with the CIE coordinates x=0.51; y = 0.47) and was used either as a dopant or as an ultra-thin layer in a blue-emitting matrix of 4,4'-bis(2,2'-diphenylvinyl)-1,1'-biphenyl (DPVBi). DPVBi (OcCz2CN) 2 -doped structure exhibited, at doping ratio of 1.5 weight %, a yellowish-green light with the CIE coordinates (x = 0.31; y = 0.51), an electroluminescence efficiency η EL =1.3 cd/A, an external quantum efficiency η ext = 0.4 % and a luminance L= 127 cd/m 2 (at 10 mA/cm 2 ) whereas for non-doped devices utilizing the carbazolic fluorophore as a thin neat layer, a warm white with CIE coordinates (x = 0.40; y= 0.43), η EL = 2.0 cd/A, η ext = 0.7 %, L = 197 cd/m 2 (at 10 mA/cm 2 ) and a color rendering index (CRI) of 74, were obtained. Electroluminescence performances of both the doped and non-doped devices were compared with those obtained with 5,6,11,12-tetraphenylnaphtacene (rubrene) taken as a reference of highly efficient yellow emitter..

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Polycarbazoles: 25 Years of Progress

Cited by 615 publications

References 166 publications

Molecular modeling and experimental studies on structure and NMR parameters of 9-benzyl-3,6-diiodo-9H-carbazole

Molecular modeling and experimental studies on structure and NMR parameters of 9-benzyl-3,6-diiodo-9H-carbazole

Expanding benzene to giant graphenes: towards molecular devices

Doped and non-doped organic light-emitting diodes based on a yellow carbazole emitter into a blue-emitting matrix

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