Synthesis and characterisation of aromatic ethynyl-bridged ferrocenes

Chawdhury, Nazia; Long, Nicholas J.; Mahon, Mary F.; Ooi, Li‐ling; Raithby, Paul R.; Rooke, Stephanie J.; White, Andrew J. P.; Williams, David J.; Younus, Muhammad

doi:10.1016/j.jorganchem.2003.11.035

Cited by 47 publications

(15 citation statements)

References 64 publications

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“…Toluene was used instead of THF because of the poor solubility of diiodoanthraquinone in THF. Compound 1 was earlier synthesized by Chawdhury et al . but the crystal structure was not analysed .…”

Section: Resultsmentioning

confidence: 99%

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Ferrocene‐substituted bis(ethynyl)anthracene compounds as anticancer agents

Singh

Kumari

Raghuvanshi

et al. 2017

Applied Organom Chemis

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Three compounds (1–3) were synthesized, where ethynylferrocene is substituted at different positions of anthracene and anthraquinone, and their biological properties were investigated. Compounds 1–3 were characterized using NMR and mass spectroscopies and confirmed by their single‐crystal X‐ray structure. They were also characterized from electronic and photophysical properties. All three crystal structures were optimized using density functional theory calculations. The presence of C–H⋅⋅⋅π interactions in 1–3 leads to the formation of two‐ and three‐dimensional networks. The bioactivity of 1–3 was expressed by molecular docking with various cancerous proteins, which participated in progression of cancer. Compound 2 displayed the best interaction with cancer‐related Aurora A protein in terms of both binding energy (−10.61 kcal mol−1) as well as inhibition constant (16.74 nM). The molecular docking result also coincides with cytotoxicity on cancer cell lines (A375, HeLa) and DNA/protein binding affinity.

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Section: Resultsmentioning

confidence: 99%

“…Compound 1 was earlier synthesized by Chawdhury et al . but the crystal structure was not analysed . Compounds 1 , 2 and 3 were characterized using 1 H NMR and 13 C NMR spectroscopies and high‐resolution mass spectrometry (HRMS) and authenticated by single‐crystal X‐ray diffraction.…”

Section: Resultsmentioning

confidence: 99%

Ferrocene‐substituted bis(ethynyl)anthracene compounds as anticancer agents

Singh

Kumari

Raghuvanshi

et al. 2017

Applied Organom Chemis

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“…It is worth mentioning that optically induced intramolecular electron transfer processes have been previously reported in electrochemically active ferrocenyl-thiophene derivatives [ 46 – 50 ]. Moreover, it has also been reported that the intramolecular electron transfer phenomena can be monitored by the study of the intervalence charge-transfer bands (IVCT) occurring in the electrochemically oxidized state of this type of π-bridged systems [ 51 – 55 ].…”

Section: Resultsmentioning

confidence: 99%

Nitrogen-Rich Multinuclear Ferrocenophanes as Multichannel Chemosensor Molecules for Transition and Heavy-Metal Cations

Sola

Espinosa

Tárraga

et al. 2014

Sensors

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[m.n] Multinuclear ferrocenophanes prepared by aza-Wittig reaction of bisiminophosphoranes derived from 1,1′-diazidoferrocene and isophthaladelhyde or 2,5-diformylthiophene, behave as efficient electrochemical and chromogenic chemosensor molecules for Zn2+, Pb2+, and Hg2+ metal cations. Whereas the OSWV of receptor 3, bearing two m-phenylene units in the bridges, display one oxidation peak, receptor 4 incorporating two thiophene rings in the bridges, exhibits two well-separated oxidation peaks. In both receptors only the addition of Zn2+, Pb2+, and Hg2+ metal cations induced a remarkable anodic shift of ferrocene/ferrocenium redox couple. Likewise, in the absorption spectra of these receptors the low energy band is red-shifted by Δλ = 165 − 209 nm, and these changes promoted a significant color changes which could be used for the naked eye detection of these metal cations. The coordination modes for two representative cases were unveiled by DFT calculations that show an unsual coordination in the [42Pb]2+ complex with the Pb2+ cation in a distorted cubic N4S4 donor cage.

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“…Among the methods described, Sonogashira coupling has been the most extensively used due to its good yield and better quality of end product [35]. Furthermore, most of the terminal ethynyl compounds are not stable in air and at ambient temperature.…”

Section: Type I Ferrocene Materialsmentioning

confidence: 99%

Ferrocenylethynyl - a versatile platform for new molecules to novel materials

Shah

Al-Belushi

Khan

2014

SQU Journal for Science

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Ferrocenylethynyl is a key starting material for the synthesis of fascinating new molecules and novel functional materials. It combines the robust and redox-active ferrocene moiety with the rigid-rod ethynyl unit. The ferrocene center provides chemically and electrochemically switchable material properties whereas the ethynyl backbone facilitates electron delocalization along the molecule, yielding materials with the potential for a wide range of applications from sensors to bio-organometallics and pharmaceuticals, from catalysts to nonlinear optical materials, and from fuel additives to chelating agents. However, lifetime performances and costs still need to be optimized to make ferrocenylethynyl-based materials commercially competitive. Efficient synthetic methods are already in place which could play a key role in the progress of these materials. This review discusses the main approaches adopted in the synthesis of ferrocenylethynyl-based molecules and materials. Representative examples of each method are reported, highlighting its significant achievements together with the open issues and challenges to be faced by future researchers in this area.

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Synthesis and characterisation of aromatic ethynyl-bridged ferrocenes

Cited by 47 publications

References 64 publications

Ferrocene‐substituted bis(ethynyl)anthracene compounds as anticancer agents

Ferrocene‐substituted bis(ethynyl)anthracene compounds as anticancer agents

Nitrogen-Rich Multinuclear Ferrocenophanes as Multichannel Chemosensor Molecules for Transition and Heavy-Metal Cations

Ferrocenylethynyl - a versatile platform for new molecules to novel materials

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