Synthesis and Reactivity of a Strained Silicon‐Bridged [1]Ferrocenophanium Ion

Masson, Georgeta; Herbert, David E.; Whittell, George R.; Holland, Jason P.; Lough, Alan J.; Green, Jennifer C.; Manners, Ian

doi:10.1002/anie.200901213

Cited by 17 publications

(29 citation statements)

References 40 publications

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“…This is consistent with the onset of LMCT-type transitions that lend ferrocenium its typical blue color. 44,52 Isosbestic points are evident at 431 and 518 nm. In addition, higher energy absorptions grow in intensity, with a prominent peak appearing at 265 nm and an intense shoulder at ∼364 nm.…”

Section: ■ Results and Discussionmentioning

confidence: 98%

Catalytic Synthesis of Donor-Acceptor-Donor (D-A-D) and Donor-Acceptor-Acceptor (D-A-A) Pyrimidine-Ferrocenes via Acceptorless Dehydrogenative Coupling: Synthesis, Structures, and Electronic Communication

et al. 2021

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The synthesis and full characterization of a series of ferrocene-decorated pyrimidines with donor-acceptor-donor (D-A-D) and donor-acceptor-acceptor (D-A-A) architectures are reported. The three novel compounds share a pyrimidine core and single ferrocenyl donor arm, with an additional substituent varied from donor ferrocene (1) to acceptor pyrenyl (2) to donor (4-diphenylamino)phenyl groups (3). The compounds could be easily constructed in acceptable yields in one-pot reactions via acceptorless dehydrogenative coupling reactions mediated by a ruthenium coordination complex supported by a simple bidentate P^N ligand. The solution and solid-state structures of the new pyrimidines are described along with photophysical and computational characterization. The lack of near IR (NIR) transitions upon single-electron oxidation of the compounds implies that the pyrimidinyl unit is less effective at mediating electronic communication compared with pyridine or pyrrole cores. Nevertheless, strong absorption in the far visible and NIR is observed upon formation of a dicationic species from 3 and is attributed to efficient charge transfer from the pyrimidine core to the oxidized donor units.

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Section: ■ Results and Discussionmentioning

confidence: 98%

Catalytic Synthesis of Donor-Acceptor-Donor (D-A-D) and Donor-Acceptor-Acceptor (D-A-A) Pyrimidine-Ferrocenes via Acceptorless Dehydrogenative Coupling: Synthesis, Structures, and Electronic Communication

et al. 2021

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“…Figure C shows the recorded UV‐visible spectra of ferrocenium ion stabilized with a polyelectrolyte in solution. The characteristic of the ferrocenium ion is Ligand‐to‐metal charge‐transfer (LMCT) absorption band at 620 nm wavelength, with low extinction coefficient [Figure C inset]. This band was assigned to a transition from the e 1u π orbitals of the cyclopentadienyl ligands to the hole in the metal‐based e 2g level, and its intensity is attributed to the charge‐transfer nature of the transition.…”

Section: Resultsmentioning

confidence: 99%

Ferrocenium Ion Confinement in Polyelectrolyte for Electrochemical Nitric Oxide Sensor

et al. 2019

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Manuscript reports on ferrocenium ion entangled in polyelectrolyte matrix as a redox platform for oxidative and reductive sensing of nitric oxide (NO). It was prepared by oxidation of ferrocene in diethyl ether followed by extraction with polystyrene sulfonic acid (PSS) and Nafion® solution. The presence of stable ferrocenium cation was confirmed by FT-IR, UV-visible spectra, 1 HNMR and XRD. It results into a stable cyclic voltammogram in 100 mM Phosphate buffer, pH 7 solution with Ag/AgCl reference and Pt wire counter electrodes. The electrode sensitivity towards NO was confirmed through the increase in oxidative current at + 750 mV and reductive current at À 800 mV by the addition of 100 μL saturated NO solution. The chronoamperometric response for NO oxidation followed linearity in the concentration range of 200 nM to 3.5 μM. The lower detection limit and sensitivity were found to be 200 nM and be 33.29 μA/μM/cm 2 respectively. The reductive response also followed a linear trend in the concentration range of 100 μM to 1.2 mM with 15.15 μA/μM/cm 2 sensitivity and 100 μM detection limit. It indicates ferrocenium ion entanglement within polyelectrolyte matrix and its viability as a redox platform for oxidative as well as reductive sensing of nitric oxide.

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“…The identity of the metal and bridging moiety in [ n ]metallocenophanes dictates their properties, affecting the nature and location of bond cleavage and the subsequent reactivity pathways. Furthermore, changes in the redox state of [ n ]metallocenophanes can play an important additional role by altering their ansa structure and electron distribution, as illustrated by studies describing the synthesis and reactivity of a [1]ferrocenophanium ion 8…”

Section: Methodsmentioning

confidence: 99%

MetalMetal Bond Formation Between [n]Metallocenophanes: Synthesis and Characterisation of a Dicarba[2]ruthenocenophanium Dimer

Russell

Gilroy

Lam

et al. 2012

Chemistry A European J

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Synthesis and Reactivity of a Strained Silicon‐Bridged [1]Ferrocenophanium Ion

Cited by 17 publications

References 40 publications

Catalytic Synthesis of Donor-Acceptor-Donor (D-A-D) and Donor-Acceptor-Acceptor (D-A-A) Pyrimidine-Ferrocenes via Acceptorless Dehydrogenative Coupling: Synthesis, Structures, and Electronic Communication

Catalytic Synthesis of Donor-Acceptor-Donor (D-A-D) and Donor-Acceptor-Acceptor (D-A-A) Pyrimidine-Ferrocenes via Acceptorless Dehydrogenative Coupling: Synthesis, Structures, and Electronic Communication

Ferrocenium Ion Confinement in Polyelectrolyte for Electrochemical Nitric Oxide Sensor

MetalMetal Bond Formation Between [n]Metallocenophanes: Synthesis and Characterisation of a Dicarba[2]ruthenocenophanium Dimer

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