2,4-Bis(arylethynyl)-9-chloro-5,6,7,8-tetrahydroacridines: synthesis and photophysical properties

Tka, Najeh; Ayed, Mohamed Adnene Hadj; Braiek, Mourad Ben; Jabli, Mahjoub; Chaaben, N.; Alimi, K.; Jopp, Stefan; Langer, Peter

doi:10.3762/bjoc.17.115

Cited by 6 publications

(3 citation statements)

References 70 publications

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“…74 The Sonogashira reaction of 209 with two equivalents of alkynes gave 2,4-dialkynyl-9-chloro-5,6,7,8-tetrahydroacridines 211a – g in good to excellent yields. 75 The regioselectivity can be explained by the better leaving group ability of bromide as compared to chloride, despite the effect that the chloride is located in a rather activated position in the pyridine moiety. It is interesting to note that trifold coupling reactions could not be realized at all.…”

Section: Miscellaneousmentioning

confidence: 99%

Cross-Coupling Reactions of Polyhalogenated Heterocycles

Langer

2022

Synlett

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Palladium-catalyzed cross-coupling reactions of polyhalogenated heterocycles provide a convenient access to multifold arylated and alkynylated ring systems with a broad spectrum of physical and medicinal properties. Products include thiophenes, selenophenes, pyrroles, indoles, furans, benzofurans, pyrazoles, pyridines, quinolines, pyrimidines, pyrazines, naphthyridines, quinoxalines, and others. The regioselectivity of the coupling reactions is controlled by a combination of electronic and steric parameters. While a number of couplings can be carried out essentially under standard conditions, others require the use of more sophisticated ligands and a thorough optimization of the conditions, such as solvent, temperature, or reaction time. The present Account provides a personalized overview of coupling reactions of polyhalogenated heterocycles.1 Introduction2 Thiophenes3 Selenophenes4 Pyrroles and Indoles5 Furans and Benzofurans6 Pyrazoles7 Pyridines8 Quinolines9 Pyrimidines and Pyrazines10 Naphthyridines and Quinoxalines11 Miscellaneous12 Conclusions

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Section: Miscellaneousmentioning

confidence: 99%

Cross-Coupling Reactions of Polyhalogenated Heterocycles

Langer

2022

Synlett

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“…Density functional theory (DFT) that was revealed in accordance with this goal uses the electron density to identify the reactivity or stability [ 11 – 17 ]. It should be noted that hybrid functional such as B3LYP and M062 are widely preferred in the studies regarding the explanation of reactivity properties of molecules [ 18 – 24 ]. Additionally, in the studies also researching organic light emitting diode performances of various molecules, the aforementioned functional have been used [ 25 – 31 ].…”

Section: Introductionmentioning

confidence: 99%

Theoretical analysis of OLED performances of some aromatic nitrogen-containing ligands

ELİK

2023

Turkish Journal of Chemistry

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It is well-known that tris(8-hydroxyquinoline) aluminum (Alq3) complex and N,N′diphenyl-N,N′-bis(3-methylphenyl)-1,1′-diphenyl-4,4′-diamine compound (TPD) are widely used as electron transfer material (ETL) and hole transfer material (HTL) in organic light emitting diode (OLED) structure, respectively. Considering the reference materials, in the present work, the OLED performances of some cyclic aromatic structures such as 4,4′azopyridine [AZPY], 4,4′-bipyridine [BIPY], 1,2-bis[4′-(4-methylphenyl)2,2′:6′2″-terpyridin6-yl]ethyne (BISTERPY), 5,5′-diamino-2,2′-bipyridine (DABP), dipyrido[3,2-a:2′,3′c]phenazine (DPP), 4,7-phenanthroline (PHEN) including nitrogen atom have been theoretically analyzed. It is important to note that B3LYP/6-31G(d) and B3LYP/TZP levels of the theory were taken into account for the calculations about monomeric and dimeric structures, respectively. Additionally, the calculations of the mentioned monomeric form were performed at B3LYP-D3/6-31G, CAM-B3LYP/6-31G and ωB97X-D/6-31G(d) levels. For a detailed theoretical analysis, the reorganization energies (λe and λh), adiabatic and vertical ionization potentials and electron affinities, the effective transfer integrals (Ve and Vh), and the charge transfer rates (We and Wh) of all compounds were computed by means of computational chemistry tools. In the light of calculated parameters, it is determined that these mentioned aromatic cyclic structures will be used in which layers of OLED structure. The results obtained in this study will be helpful in the design and applications of new molecules as OLED materials in the future.

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“…Recently, considerable attention has been given to acridines in our laboratory and we developed new synthetic methods for dibenzoacridines and acridones based on Pd-catalyzed cross-coupling reactions [ 55 – 56 ]. More recently, we have reported the synthesis of alkynylated 5,6,7,8-tetrahydroacridines [ 57 ]. In continuation to our previous work and as a part of our interest in new organic materials [ 58 – 60 ], we report herein the synthesis of hitherto unknown 2,4-diaryl-9-chloro-5,6,7,8-tetrahydroacridine derivatives and their optical and electrochemical properties investigation by the use of UV–vis and emission spectroscopy, CV measurements as well as DFT calculations.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and investigation on optical and electrochemical properties of 2,4-diaryl-9-chloro-5,6,7,8-tetrahydroacridines

Tka¹,

Ayed²,

Braiek³

et al. 2021

Beilstein J. Org. Chem.

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A facile synthesis of 2,4-diaryl-9-chloro-5,6,7,8-tetrahydroacridine derivatives is reported which is based on POCl3-mediated cyclodehydration followed by double Suzuki–Miyaura cross-coupling. The absorption and fluorescence properties of the obtained products were investigated and their HOMO/LUMO energy levels were estimated by cyclic voltammetry measurements. Besides, density functional theory calculations were carried out for further exploration of their electronic properties.

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2,4-Bis(arylethynyl)-9-chloro-5,6,7,8-tetrahydroacridines: synthesis and photophysical properties

Cited by 6 publications

References 70 publications

Cross-Coupling Reactions of Polyhalogenated Heterocycles

Cross-Coupling Reactions of Polyhalogenated Heterocycles

Theoretical analysis of OLED performances of some aromatic nitrogen-containing ligands

Synthesis and investigation on optical and electrochemical properties of 2,4-diaryl-9-chloro-5,6,7,8-tetrahydroacridines

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