Iron Catalyzed Cascade Protocol for the Synthesis of Pyrrolo[1, 2‐<i>a</i>]quinoxalines: A Powerful Tool to Access Solid State Emissive Organic Luminophores

Lade, Jatin J.; Patil, Bhausaheb N.; Sathe, Pratima A.; Vadagaonkar, Kamlesh S.; Chetti, Prabhakar; Chaskar, Atul

doi:10.1002/slct.201701383

Cited by 26 publications

(7 citation statements)

References 34 publications

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“…The first step involved a Buchwald-type C−N coupling of bromoaldehyde (2) with phenoxazine (1) and phenothiazine (4). 21 The intermediates (3 and 5) were then condensed with 1-(2-aminophenyl)pyrrole (6) in the presence of Lewis-acid catalyst FeCl 3 to yield POZ−PQ and PTZ−PQ, respectively. 22 In addition, PTZ-SA was synthesized by a condensing intermediate (5) with 2-aminobenzenesulfonamide in the presence of NaHSO 3 .…”

Section: Methodsmentioning

confidence: 99%

Exciplex forming a Phenyl-Spaced Phenoxazine D–A Cohost for a Highly Efficient Red-Phosphorescent Organic Light-Emitting Diode

Ganesan,

Balasubramaniam,

Lade

et al. 2023

ACS Appl. Opt. Mater.

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Spaced bipolar D–A molecules were designed for application as host materials for phosphorescent organic light-emitting diode (PhOLED) devices. Three molecules (POZ–PQ, POZ-SA, and PTZ–PQ) with a phenyl linker between the donor (phenoxazine and phenothiazine) and acceptor were synthesized and characterized. Their thermal, photophysical, and electrochemical properties were studied and then applied in the emitting layer (EML) of the PhOLED device. A promising exciplex-forming tendency of the molecules led us to explore their application as cohosts in the EML. An excellent external quantum yield of 14.9% was achieved for the POZ–PQ:CN-T2T device.

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Section: Methodsmentioning

confidence: 99%

Exciplex forming a Phenyl-Spaced Phenoxazine D–A Cohost for a Highly Efficient Red-Phosphorescent Organic Light-Emitting Diode

Ganesan,

Balasubramaniam,

Lade

et al. 2023

ACS Appl. Opt. Mater.

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“…As an important class of nitrogen heterocyclic compounds, pyrrolo[1,2‐ α ]quinoxalines and their derivatives, contain two six‐membered rings and one five‐membered ring in their structures, and have excellent biological activities for compounds containing a pyrrolo[1,2‐ α ]quinoxaline fragment, such as anticancer, [1a] antitumor, antimalarial, [1b] inhibition of protein tyrosine phosphatase 1B, [1c] activation of Sirt2‐7, [1d] inhibition of the D‐ring activity of RAD51, [1e] etc. In addition, the three rings form a highly conjugated plane with large rigidity and exhibit extremely strong fluorescence, [2] and their modification by using different groups can modulate fluorescence of different colors, which can be used in organic electroluminescence, [3] chemical sensing detection, [4] fluorescent probe design, [5] etc, shown in Figure 1, therefore, the rapid construction of pyrrolo[1,2‐ α ]quinoxalines fragment is particularly important.…”

Section: Introductionmentioning

confidence: 99%

Recent Progress in the Catalytic Synthesis of Pyrrolo[1,2‐α]quinoxaline

Liu

Wang

2023

Asian J Org Chem

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Pyrrolo[1,2‐α]quinoxaline and its derivatives have excellent biological activity and photoelectric properties, and are widely used in the fields of pharmaceutical preparations and organic electroluminescence. This review starts from catalysts and summarizes the single metal catalysis of palladium, rhodium, iron, molybdenum, and copper, as well as the synergistic catalysis of iron molybdenum bimetallic and metal‐free catalytic systems for the synthesis of pyrrolo[1,2‐α]quinoxaline. The pyrrolo[1,2‐α]quinoxaline catalytic mechanism in the different catalytic systems was detailly introduced and analysed. By analysing the advantages and disadvantages of existing catalyst systems, the prospects of new catalysts and methods for synthesis of pyrrolo[1,2‐α]quinoxaline are presented.

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“…They can also act as human protein kinase CK2 inhibitors, glucagon receptor antagonists, and 5-HT 3 receptor antagonists . In addition to exhibiting biological activity, some derivatives of 4-aryl pyrrolo[1,2-α]quinoxalines have excellent fluorescence and photophysical properties that are of great importance in the synthesis of biomarkers, dyes, and materials …”

Section: Introductionmentioning

confidence: 99%

Synthesis of 4-Aryl Pyrrolo[1,2-α]quinoxalines via Iron-Catalyzed Oxidative Coupling from an Unactivated Methyl Arene

et al. 2021

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Herein, we describe the direct synthesis of pyrrolo[1,2-α]quinoxaline via oxidative coupling between methyl arene and 1-(2-aminophenyl) pyrroles. Oxidation of the benzylic carbon of the methyl arene was achieved by di-t-butyl peroxide in the presence of an iron catalyst, followed by conversion to an activated aldehyde in situ. Oxygen played a crucial role in the oxidation process to accelerate benzaldehyde formation. Subsequent Pictet–Spengler-type annulation completed the quinoxaline structure. The protocol tolerated various kinds of functional groups and provided 22 4-aryl pyrrolo[1,2-α]quinoxalines when various methyl arene derivatives were used. The developed method proceeded in air, and all catalysts, reagents, and solvents were easily accessible.

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Iron Catalyzed Cascade Protocol for the Synthesis of Pyrrolo[1, 2‐a]quinoxalines: A Powerful Tool to Access Solid State Emissive Organic Luminophores

Cited by 26 publications

References 34 publications

Exciplex forming a Phenyl-Spaced Phenoxazine D–A Cohost for a Highly Efficient Red-Phosphorescent Organic Light-Emitting Diode

Exciplex forming a Phenyl-Spaced Phenoxazine D–A Cohost for a Highly Efficient Red-Phosphorescent Organic Light-Emitting Diode

Recent Progress in the Catalytic Synthesis of Pyrrolo[1,2‐α]quinoxaline

Synthesis of 4-Aryl Pyrrolo[1,2-α]quinoxalines via Iron-Catalyzed Oxidative Coupling from an Unactivated Methyl Arene

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