Anthracene-based Ni(II) thiosemicarbazones with novel intramolecular π–π stackings

Nguyen, Minh-Viet; Khuat, Thi-Thuy-Ha; Do, Danh-Quang; Nguyen, Hoai Thuong; Dinh, Thi-Hien

doi:10.1016/j.inoche.2020.107994

Cited by 8 publications

(3 citation statements)

References 38 publications

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“…Besides, the disappearance of proton signals arising from H1,8,2,7 is detected. The abnormal signal pattern is understandable in view of reported X-ray structures of similar Ni(II) complexes [7]. In the reported structures, anthracene rings are in cis arrangement with intramolecular π-π stacking.…”

Section: Synthesismentioning

confidence: 64%

“…Indeed, weak interactions such as π-π stackings among the thiosemicarbazone ligands are needed to sustain the cis arrangements [4,5]. Our group also reported anthracene-based and pyrenebased Ni(II) thiosemicarbazone complexes which showed cis geometries cemented by intramolecular π-π interactions [6,7]. In this paper, a new Ni(II) complex with anthracenebased thiosemicarbazone (NiL) is presented.…”

Section: Introductionmentioning

confidence: 98%

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Synthesis and Spectroscopic Characterizations of Ni(II) Thiosemicarbazone Bearing Anthracene

Hien¹,

Ha²,

Đạt³

et al. 2021

NST

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The X-ray structure of 9-anthraldehyde-4-methyl-3-thiosemicarbazone was firstly determined. The Ni(II) complex with this ligand was prepared upon reaction with chloride salt. Mass spectrometry result confirms correct formulation of the complex. Unusual 1H NMR signal pattern of anthracene moiety reveal cis arrangement cemented by intramolecular p–p stackings between aromatic rings. As a result of this interaction, the electronic structure of anthracene ring is perturbed and gives rise to structureless and broad absorption and emission bands.

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Section: Synthesismentioning

confidence: 64%

Section: Introductionmentioning

confidence: 98%

Synthesis and Spectroscopic Characterizations of Ni(II) Thiosemicarbazone Bearing Anthracene

Hien¹,

Ha²,

Đạt³

et al. 2021

NST

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“…9-Anthraldehydes or anthracene-9-carbaldehydes ( 1 ) are important intermediates for dyes, sensors, and pharmaceutical ingredients (Figure ). In addition, some 9-anthraldehydes have been employed as building blocks for supramolecular assemblies and in the preparation of Schiff bases ( 2 – 3 ) as well as other functionalized ligands. , Moreover, 9-anthraldehyde oxime ( 4 ), prepared from 9-anthraldehyde, has served as a starting material for various functionalizations …”

Section: Introductionmentioning

confidence: 99%

Substituted 9-Anthraldehydes from Dibenzocycloheptanol Epoxides via Acid-Catalyzed Epoxide Opening/Semipinacol Rearrangement

et al. 2021

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Starting from benzaldehyde derivatives, the corresponding dibenzocycloheptenol could be prepared in five steps. Under both substrate (secondary vs tertiary alcohol and the substituents on the aromatic ring(s)) and condition control, the subsequent epoxidation and acid-catalyzed epoxide opening/semipinacol rearrangement/aromatization afforded the corresponding 9-anthraldehydes in good yields, up to 88% over two steps. The presence of the electron-withdrawing group(s) on the aromatic ring(s) suppressed the rate of the epoxidation while the subsequent semipinacol rearrangement step required heating; the presence of the electron-donating group(s), on the other hand, frequently led to the decomposition during the epoxidation. From the mechanistic studies, the semipinacol rearrangement of the epoxide could precede the ionization at the bisbenzylic position, yielding the aldehyde intermediate. The ensuing dehydrative aromatization led to the formation of 9-anthraldehyde. Conversely, nucleophilic addition to the aldehyde and dehydrative aromatization with concomitant loss of formic acid led to anthracene.

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Functionalised anthracene chemosensors: kinetics and molecular logic gate operations

Ashwathi,

Bhuvanesh,

Basheer

2024

Res Chem Intermed

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Anthracene-based Ni(II) thiosemicarbazones with novel intramolecular π–π stackings

Cited by 8 publications

References 38 publications

Synthesis and Spectroscopic Characterizations of Ni(II) Thiosemicarbazone Bearing Anthracene

Synthesis and Spectroscopic Characterizations of Ni(II) Thiosemicarbazone Bearing Anthracene

Substituted 9-Anthraldehydes from Dibenzocycloheptanol Epoxides via Acid-Catalyzed Epoxide Opening/Semipinacol Rearrangement

Functionalised anthracene chemosensors: kinetics and molecular logic gate operations

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