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

ABSTRACT: Acridine derivatives have attracted considerable interest in numerous areas owing to their attractive physical and chemical properties. Herein, starting from readily available anthranilic acid, an efficient synthesis of 2,4-bis(arylethynyl)-9-chloro-5,6,7,8-tetrahydroacridine derivatives was accomplished via a one-pot double Sonogashira cross-coupling method. The UV-visible absorption and emission properties of the synthesized molecules have been examined. Additionally, theoretical studies based on density functional theory (DFT/B3LYP/6-31G(d)) were carried out.

SUBMITTER: Tka N

PROVIDER: S-EPMC8290096 | biostudies-literature | 2021

REPOSITORIES: biostudies-literature

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

Tka Najeh N Ayed Mohamed Adnene Hadj MAH Braiek Mourad Ben MB Jabli Mahjoub M Chaaben Noureddine N Alimi Kamel K Jopp Stefan S Langer Peter P

Beilstein journal of organic chemistry 20210716

Acridine derivatives have attracted considerable interest in numerous areas owing to their attractive physical and chemical properties. Herein, starting from readily available anthranilic acid, an efficient synthesis of 2,4-bis(arylethynyl)-9-chloro-5,6,7,8-tetrahydroacridine derivatives was accomplished via a one-pot double Sonogashira cross-coupling method. The UV-visible absorption and emission properties of the synthesized molecules have been examined. Additionally, theoretical studies based ...[more]

PMID: 34354771

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

Project description: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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Design and Synthesis of New 5-aryl-4-Arylethynyl-1H-1,2,3-triazoles with Valuable Photophysical and Biological Properties.

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Synthesis and photophysical properties of novel bis-quinolin-3-yl-chalcones.

Project description:A novel series of unsymmetrical bis-quinolin-3-yl chalcones has been synthesized under visible light using a Claisen-Schmidt condensation reaction between the 2-(morpholine-piperidine-pyrrolidine-thiomorpholine) substituted quinoline-3-carbaldehyde and 1-(2-methyl-4-phenylquinolin-3-yl) ethan-1-one derivatives, conducted at room temperature in the presence of NaOH/EtOH. The structures of the synthesized compounds have been confirmed by NMR spectroscopy and high-resolution mass spectroscopy. The synthesized compounds exhibit λ max values ranging from 215 nm to 290 nm in non-polar to polar solvents, demonstrating positive solvatochromism. Compounds containing nitro group substituent exhibit a significant blue shift owing to their strong electron-withdrawing ability, which also contributes to fluorescence quenching. Geometrical optimization and the calculation of HOMO, LUMO, and energy gap are calculated by using the DFT/B3LYP/6-31G(d) method.

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Synthesis and Photophysical Properties of Polycarbo-Substituted Quinazolines Derived from the 2-Aryl-4-chloro-6-iodoquinazolines.

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4,5-Bis(arylethynyl)-1,2,3-triazoles-A New Class of Fluorescent Labels: Synthesis and Applications.

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Dinuclear Rhenium Complexes with a Bridging Helicene-bis-bipyridine Ligand: Synthesis, Structure, and Photophysical and Chiroptical Properties.

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(E,E)-2,5-Bis(5-chloro-2-methoxyphenyl)-3,4-diazahexa-2,4-diene.

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Photophysical and Photobiological Properties of Dinuclear Iridium(III) Bis-tridentate Complexes.

Project description:A series of cationic dinuclear iridium(III) complexes (Ir1-Ir5) bearing terpyridine-capped fluorenyl bridging ligands and different polypyridyl or cyclometalating terminal tridentate ligands were synthesized, characterized, and evaluated for their photophysical and photobiological activities. The influence of the bridging and terminal ligands on the photophysical properties of the complexes was investigated by UV-vis absorption, emission, and transient absorption spectroscopy and simulated by TDDFT calculations. All of the complexes displayed strong bridging-ligand localized visible 1π,π* absorption and red- or near-infrared phosphorescence as well as broad triplet excited-state absorption across both visible and NIR wavelengths. These triplet states were assigned as predominantly 3π,π* for Ir1 (τ = 3.1 μs) and Ir4 (τ = 48 μs) and 3CT (charge transfer) for Ir2, Ir3, and Ir5 (τ = 1.7-2.7 μs). Complexes Ir1-Ir5 acted as in vitro photodynamic therapy (PDT) agents toward human SK-MEL-28 melanoma cells when activated with visible light, with submicromolar photocytotoxicity and phototherapeutic indices ranging from 20 to almost 300. The in vitro PDT effects with visible light did not correlate with singlet oxygen (1O2) quantum yields or DNA photocleaving capacity probed under cell-free conditions. All of the Ir(III) complexes phosphoresced brightly when associated with compromised cells (with or without light treatment) and exhibited photoactivated cellular uptake, highlighting the theranostic potential of this new class of Ir(III) complex photosensitizers.

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