Heterocyclic anthrazoline derivatives: a critical review

Santos, Giovanny Carvalho dos; Moreno, Vitor Fernandes; Silva, Bruno Henrique Sacoman Torquato da; Silva‐Filho, Luiz Carlos da

doi:10.1039/c9nj04995a

Cited by 7 publications

(6 citation statements)

References 73 publications

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“… , The reaction mainly afforded two isomeric products, namely, 4,7-phenanthroline derivative P1 and 1,6-anthrazoline derivative A1 . Contrary to previous studies, − a phenanthroline derivative ( P1 ) was obtained as the major product of the reaction. Compounds P1 (52% yield) and A1 (9% yield) could be isolated as analytically pure samples by careful column chromatography and recrystallization.…”

Section: Resultscontrasting

confidence: 66%

“…The Povarov reaction is regarded as an annulative π-extension reaction , and is used for the synthesis of aza-polycyclic aromatic hydrocarbons (aza-PAHs), which possess attractive optical and semiconducting properties. − To synthesize aza-PAHs, multiple Povarov reactions have to proceed on a single substrate, making site selectivity an issue. For example, the Povarov reaction of 1,4-diaminobenzene yields two types of products, 1,6-anthrazoline and 4,7-phenanthroline derivatives (Scheme b). − This study investigated the site selectivity of the Povarov reaction with simple diaminobenzenes to gain insights into the application of this reaction for the synthesis of aza-PAHs. Based on the insights, a 1,5,9-triazatriphenylene derivative was synthesized via a triple Povarov reaction.…”

Section: Introductionmentioning

confidence: 99%

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One-Pot Synthesis of Triazatriphenylene Using the Povarov Reaction

et al. 2021

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The Povarov reaction combines aromatic amines, aldehydes, and alkynes in a single step and is regarded as an annulative π-extension reaction of aromatic amines. In this study, the Povarov reaction was investigated as an efficient tool for the synthesis of aza-polycyclic aromatic hydrocarbons via multiple π-extensions. The double Povarov reaction of 1,4-diaminobenzene yielded the 4,7phenanthroline derivative as the major product, regardless of the steric repulsion in the product. The site selectivity mainly depended on the HOMO distribution of the intermediate rather than the steric factor. Based on these insights, a 1,5,9-triazatriphenylene derivative was synthesized via a triple Povarov reaction. The structures of the synthesized compounds were unambiguously determined by single-crystal X-ray diffraction analysis. The triazatriphenylene derivative formed a smooth and stable thin film upon vacuum vapor deposition and served as a hole-blocking material in organic light-emitting diodes.

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Section: Resultscontrasting

confidence: 66%

Section: Introductionmentioning

confidence: 99%

One-Pot Synthesis of Triazatriphenylene Using the Povarov Reaction

et al. 2021

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“…The Povarov reactions of aromatic diamines and triamines afford aza‐polycyclic aromatic hydrocarbons (aza‐PAHs) with large π‐conjugations [30–34] and attractive optical and semiconducting properties [35–39] . The multiple Povarov reactions of aromatic diamines face significant challenges: reduction of the imine intermediates [32] and regioselectivity (Scheme 1b) [30–34,40] . Because the imine substitutes receive hydrogens in the oxidation process on the other side, a second Povarov reaction does not occur [32] .…”

Section: Introductionmentioning

confidence: 99%

“…[17][18][19][20][21][22] In recent years, this methodology has been applied for the synthesis of quinoline-based polymers, [23][24][25] macrocycles, [26] porous cages, [27] and covalent organic frameworks. [28,29] The Povarov reactions of aromatic diamines and triamines afford aza-polycyclic aromatic hydrocarbons (aza-PAHs) with large π-conjugations [30][31][32][33][34] and attractive optical and semiconducting properties. [35][36][37][38][39] The multiple Povarov reactions of aromatic diamines face significant challenges: reduction of the imine intermediates [32] and regioselectivity (Scheme 1b).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Triazatriphenylene Derivative Through Multi‐Component Reaction of Aryl‐amine, Aldehyde, and Alkyne

et al. 2023

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The Povarov reaction is a representative multicomponent reaction used for synthesizing nitrogen‐containing aromatic compounds from aromatic amines, aldehydes, and dienophiles, such as electron‐rich alkenes and alkynes. In this study, we investigated a triple Povarov reaction of 1,3,5‐triaminobenzne with aromatic aldehydes and phenylacetylene to obtain triazatriphenylene derivatives. Reactions with arylaldehydes containing electron‐donating groups proceeded smoothly to provide triazatriphenylene derivatives. In contrast, reactions with arylaldehydes containing electron‐withdrawing groups resulted in low yields. Reactions with electron‐rich arylaldehydes are probably more favorable in terms of high stability of imine intermediates and smooth electrophilic cyclization. Single‐crystal X‐ray structure analysis revealed that the aryl groups derived from the aldehydes had small dihedral angles between with the triazatriphenylene core. The derivative with tertiary butyl groups (tBu‐TaT) had a high glass transition temperature, while that without tertiary butyl groups (H‐TaT) had a lower highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) level and served as an efficient hole‐blocking material with better electron transport properties than those of tBu‐TaT. This study provides insights into the scope and limitations of the multicomponent reactions based on the Povarov reaction, substituent dependence on the crystal structures, and physical properties of π‐extended nitrogen‐containing aromatic compounds.

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“…As humans explore the physical world, scientists are using more and more detection techniques. Initially, people observed macroscopic natural phenomena with the naked eye and summarized the laws of nature [1][2]. Humans then use magnifying glasses and microscopes to observe some microscopic objects.…”

Section: Introductionmentioning

confidence: 99%

Two-dimensional and Third-order Nonlinear Laser Spectroscopy of Fused Heterocyclic Derivatives

2022

IJFET

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In optical research, the birth of laser has brought unprecedented development to the field of optics. This technology has been fully developed and applied when lasers have been developed and studied for a long time in the field of traditional spectroscopy. In addition, a lot of very important information can be received that cannot be obtained by these classical methods. The purpose of this paper is to study the two-dimensional third-order nonlinear laser spectroscopy of fused heterocyclic derivatives. A new method for third-order nonlinear laser spectroscopy, and in order to judge the accuracy of the method, the cascaded equation of motion method is used for comparison. The experimental results show that the time non-local quantum master equation is a relatively accurate method for solving the time evolution of the density matrix, so the matching method can obtain accurate two-dimensional third-order spectrum when solving the spectrum.

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Heterocyclic anthrazoline derivatives: a critical review

Abstract: The anthrazolinic core is an important building block for several applications, especially those depending on the effect of light.

Cited by 7 publications

References 73 publications

One-Pot Synthesis of Triazatriphenylene Using the Povarov Reaction

One-Pot Synthesis of Triazatriphenylene Using the Povarov Reaction

Synthesis of Triazatriphenylene Derivative Through Multi‐Component Reaction of Aryl‐amine, Aldehyde, and Alkyne

Two-dimensional and Third-order Nonlinear Laser Spectroscopy of Fused Heterocyclic Derivatives

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