Synthesis, Structure and Properties of Fused π‐Extended Acridone Derivatives

Gao, Hongshuai; Zhang, Gang

doi:10.1002/ejoc.202000871

Cited by 12 publications

(5 citation statements)

References 76 publications

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“…Acridone and its derivatives have very similar structures as xanthone and thioxanthone, and they have been widely applied in pharmaceutical development, − new materials, − and biological probes. − Their fluorescence quantum yields were reported to be higher than those of xanthone and thioxanthone. , Recently, one acridone derivative ( N -methyl-difluoro-acridone), which emits blue fluorescence with a quantum yield of 0.87 in methanol, has been shown to have the ability to covert both singlet and triplet exactions into light even though no singlet–triplet equilibrium state is observed and thus it is potentially suitable as a blue OLED emitter . A previous theoretical study by Marian and Rai-Constapel suggested that equilibrium between 1 ππ* and 3 n O π* states could exist in acridone since ISC and rISC can take place on a picosecond timescale when it is in acetonitrile .…”

Section: Introductionmentioning

confidence: 99%

Direct Observation of Ultrafast Access to a Solvent-Independent Singlet–Triplet Equilibrium State in Acridone Solutions

Wang

Pan

et al. 2021

J. Phys. Chem. B

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Acridone and its derivatives have potential application as emitters for highly efficient blue organic light-emitting diodes (OLEDs). In this paper, we demonstrated ultrafast access of a solvent-independent singlet−triplet equilibrium state in acridone solutions by using femtosecond time-resolved spectroscopy. Our spectral data show that due to highly effective forward and reverse intersystem crossing (both k ISC and k rISC over 10 10 s −1 ), a singlet−triplet equilibrium state is always populated in acridone in all solvents studied. However, the lifetimes of the equilibrium state varied a lot in different solvent environments and the final decay pathway of this state can switch between high quantum yield fluorescence emission and further internal conversion to the lowest triplet state. These findings provide direct experimental evidence to understand the distinct photophysical behaviors of acridone and also provide guidance for further design of acridone and its derivatives as blue OLED emitters.

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Section: Introductionmentioning

confidence: 99%

Direct Observation of Ultrafast Access to a Solvent-Independent Singlet–Triplet Equilibrium State in Acridone Solutions

Wang

Pan

et al. 2021

J. Phys. Chem. B

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“…However, such method often leads to the generation of pyridone-doped aromatic system in the angular shape with weakened conjugation of benzene at the turning region. [11] To access the acenes in the linear fashion, the palladium-catalyzed Buchwald-Hartwig amination was utilized to build the pyridone unit. [12] Treatment of the dibrominated compound 1 with Turbo Grignard reagent afforded the mono-Grignard reagent, which underwent the nucleophilic addition to the ortho-brominated aldehydes to generate the alcohols 2 in 33-52 % yields.…”

Section: Resultsmentioning

confidence: 99%

Pyridone‐Doped Acenes with Improved Stability

Yan

Ding

Zhang

2023

Chemistry A European J

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Besides the peripheral modification, the introduction of heteroatoms to modulate the property of longer acenes with improved chemical stability has been extensively studied for their potential applications in organic electronics. However, the utilization of 4‐pyridone, a common unit in the air‐ and photo‐stable acridone and quinacridone, to decorate higher acenes with increased stability has not been realized yet. Here we present the synthesis of a series of monopyridone‐doped acenes up to heptacene via the palladium‐catalyzed Buchwald‐Hartwig amination of aniline and dibromo‐ketone. The effect of pyridone on the property of doped acenes were investigated experimentally and computationally. With the π‐extension of doped acenes, the pyridone ring shows the weakened conjugation and gradual loss of aromaticity. The doped acenes demonstrate enhanced stability in solution and maintain the electronic communication between the acene planes.

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“…The acid-catalyzed intramolecular cyclization of diarylamine derivatives bearing ester function represents a valuable strategy for the construction of quinolone frameworks via Friedel-Crafts-type reaction [30]. Hence, we decided to adopt this methodology for the synthesis of azuleno [2,1-b]quinolones.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Azuleno[2,1-b]quinolones and Quinolines via Brønsted Acid-Catalyzed Cyclization of 2-Arylaminoazulenes

Shoji,

Takeuchi,

Uda

et al. 2023

Molecules

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Quinolone and quinoline derivatives are frequently found as substructures in pharmaceutically active compounds. In this paper, we describe a procedure for the synthesis of azuleno[2,1-b]quinolones and quinolines from 2-arylaminoazulene derivatives, which are readily prepared via the aromatic nucleophilic substitution reaction of a 2-chloroazulene derivative with several arylamines. The synthesis of azuleno[2,1-b]quinolones was established by the Brønsted acid-catalyzed intramolecular cyclization of 2-arylaminoazulene derivatives bearing two ester groups at the five-membered ring. The halogenative aromatization of azuleno[2,1-b]quinolones with POCl3 yielded azuleno[2,1-b]quinolines with a chlorine substituent at the pyridine moiety. The aromatic nucleophilic substitution reaction of azuleno[2,1-b]quinolines bearing chlorine substituent with secondary amines was also investigated to afford the aminoquinoline derivatives. These synthetic methodologies reported in this paper should be valuable in the development of new pharmaceuticals based on the azulene skeleton.

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Synthesis, Structure and Properties of Fused π‐Extended Acridone Derivatives

Cited by 12 publications

References 76 publications

Direct Observation of Ultrafast Access to a Solvent-Independent Singlet–Triplet Equilibrium State in Acridone Solutions

Direct Observation of Ultrafast Access to a Solvent-Independent Singlet–Triplet Equilibrium State in Acridone Solutions

Pyridone‐Doped Acenes with Improved Stability

Synthesis of Azuleno[2,1-b]quinolones and Quinolines via Brønsted Acid-Catalyzed Cyclization of 2-Arylaminoazulenes

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