Synthesis of carbazole derivatives with high quantum yield and high glass transition temperature

Zhang, Xiqi; Chi, Zhenguo; Yang, Zhiyong; Chen, Meina; Xu, Bingjia; Zhou, Lin; Wang, Yuming; Zhang, Yi; Liu, Siwei; Xu, Jiarui

doi:10.1016/j.optmat.2009.06.009

Cited by 26 publications

(10 citation statements)

References 13 publications

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“…These sulfides displayed a trend similar to analogous biphenyl-based dyes previously reported in literature; the small red-shifted absorption and fluorescence emission maxima observed among these series of related compounds is due to an increase in the electron mobility, influenced by the end-capping group, generally, an electron donating group [29][30][31][32]. From the onset of the absorption peaks ( onset = 390-400 nm), the optical band gap E g (E g = 1240/ onset )…”

supporting

confidence: 83%

Synthesis and photophysical characterization of novel π-conjugated vinyl sulfides

Bassaco¹,

Monçalves²,

Rinaldi³

et al. 2014

Journal of Photochemistry and Photobiology A: Chemistry

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supporting

confidence: 83%

Synthesis and photophysical characterization of novel π-conjugated vinyl sulfides

Bassaco¹,

Monçalves²,

Rinaldi³

et al. 2014

Journal of Photochemistry and Photobiology A: Chemistry

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“…The emission bands for D2 and D3 each show several peaks, most likely from transitions into different vibronic states of the electronic ground state. Only one main emission band can be observed for compound D1 in the polar solvent CH 3 CN, with a very high Φ F of 90 %, coincidently with an emission due to the carbazole moiety,29 whereas for D2 and D3 the emissions are very weak.…”

Section: Resultsmentioning

confidence: 95%

Arylamine‐Modified Thiazoles as Donor–Acceptor Dyes: Quantum Chemical Evaluation of the Charge‐Transfer Process and Testing as Ligands in Ruthenium(II) Complexes

et al. 2012

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A series of new 4‐hydroxy‐1,3‐thiazole‐based chromophores bearing different arylamine components (triarylamines, carbazole, and phenothiazine) as electron donors and azaheterocycle components (pyridine, pyrazine and pyrimidine) as electron‐acceptor moieties have been synthesized. Elaborate quantum chemical calculations were carried out with two selected compounds to identify the natures of the HOMO/LUMO transition and of the intramolecular charge‐transfer state. The electrochemical properties were investigated: the dyes show reversible first oxidation and reduction peaks, with the former strongly dominated by the type of arylamine. The donor moieties were synthesized under Buchwald–Hartwig conditions. Several of the presented X‐ray structures provide deeper insight into the geometries of the ligands. The bidentate nature of the chromophores makes them suitable as ligands in transition metal complexes. The corresponding ruthenium(II) polypyridine complexes – Ru(dmbpy)2(L)(PF6)2 (dmbpy = 4,4′‐dimethyl‐2,2′‐bipyridine) – were successfully synthesized for seven of the ligands. The MLCT bands in these complexes are significantly broadened, resulting in improved light‐harvesting efficiencies.

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“…4-(9H-carbazol-9-yl)benzaldehyde was synthesized by the reported procedure [17][18][19]. To the mixture of cabazole 50 mmol (8.40 g) and potassium tertbutoxide 50 mmol (5.60 g) were stirring in 200 ml DMF at 110 • C. After 30 min, 4-fluorobenzaldehyde 50 mmol (6.20g) was added dropwise during the reaction.…”

Section: 21mentioning

confidence: 99%

“…Cabazole derivative (1), namely 4-(9H-carbazol-9-yl)benzaldehyde, was easily synthesized by the reported procedure [17][18][19]. The designed novel D-π -A dyes (2)(3)(4) were synthesized by the onestep condensation of 4-(9H-carbazol-9-yl)benzaldehyde as a electron-donating unit with malononitrile for 2, 1-indanone for 3, and 1,3-indanedione for 4 as a electron-withdrawing unit, respectively.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Solvatofluorochromism Behaviors on Intramolecular Charge Transfer System of Novel D-π-A Dyes

Kim

Son

2012

Molecular Crystals and Liquid Crystals

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Solvatochromic donor-π -acceptor (D-π -A) charge transfer dyes have been great attention from the viewpoint of their applicability as probes for the determination of solvent polarity and colorimetric chemosensors. In this work, novel solvatochromic fluorophore dyes based on D-π -A charge transfer system were designed and synthesized containing a strong electron-donating unit as a carbazole moiety and three different strong electronwithdrawing units. The corresponding molecular design and the optical properties of the D-π -A dyes were examined in various solutions with widely different polarity. The prepared dyes were found to exhibit a positive fluorescence solvatochromism. Furthermore, the energy properties of these dyes were also computationally optimized and calculated by computational simulation approaches using Material Studio 4.3 and electrochemical measurement.

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Synthesis of carbazole derivatives with high quantum yield and high glass transition temperature

Cited by 26 publications

References 13 publications

Synthesis and photophysical characterization of novel π-conjugated vinyl sulfides

Synthesis and photophysical characterization of novel π-conjugated vinyl sulfides

Arylamine‐Modified Thiazoles as Donor–Acceptor Dyes: Quantum Chemical Evaluation of the Charge‐Transfer Process and Testing as Ligands in Ruthenium(II) Complexes

Synthesis and Solvatofluorochromism Behaviors on Intramolecular Charge Transfer System of Novel D-π-A Dyes

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