Ferrocene-appended porphyrins: Syntheses and properties

Bucher, Christophe; Devillers, Charles H.; Moutet, Jean‐Claude; Royal, Guy; Saint‐Aman, Eric

doi:10.1016/j.ccr.2007.11.025

Cited by 119 publications

(17 citation statements)

References 111 publications

(159 reference statements)

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“…Ferrocene has also been used in monolayers on gold and silicon surfaces, which could be applied to charge storage and communication devices. Ferrocene‐appended porphyrins are potentially useful molecular materials in self‐assembled monolayers for charge separation upon photoinduced electron transfer …”

Section: Ferrocenes In Supramolecular Ensembles Liquid Crystals Andmentioning

confidence: 99%

Why is Ferrocene so Exceptional?

2016

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The appearance of ferrocene in the middle of the 20th century has revolutionized organometallic chemistry and is now providing applications in areas as varied and sometimes initially unexpected as optical and redox devices, battery and other materials, sensing, catalysis, including asymmetric and enantioselective catalysis, and medicine. The author presents here a general, although personal, view of ferrocene's chemistry, properties, functions, and applications through a literature survey involving both historical and up‐to‐date trends and including examples of his group's research in a number of these areas. The review gathers together general features of ferrocene chemistry and representative examples of the salient aspects. Its focus is on ferrocene's basic properties, ferrocene‐containing ligands, the ferrocene/ferricinium redox couple, ferrocene mixed‐valence and average‐valence systems, the ferricinium/ferrocene redox shuttle in catalysis, ligand‐exchange reactions, ferrocene‐containing polymers, ferrocene‐containing structures for cathodic battery and other materials, ferrocenes in supramolecular ensembles, liquid crystals, and nonlinear optical materials, ferrocene‐containing stars and their electrostatic effects, ferrocene‐containing dendrons, dendrimers, and nanoparticles (NPs) and their application in redox sensing and catalysis, and ferrocenes in nanomedicine.

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Section: Ferrocenes In Supramolecular Ensembles Liquid Crystals Andmentioning

confidence: 99%

Why is Ferrocene so Exceptional?

2016

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“…[21] Theire xcellent energy-and charge-transfer capability make them advantageousi nm imicking photosyntheticp rocesses. [22] Strong electron donors,s uch as ferrocenes (Fcs) and ruthenocenes (Rcs),a re often conjugated in the vicinity of electron-accepting moieties [23,24] or used as components to improve charge-transfer properties of biomimetic systems. [25,26] From as ynthetic perspective,F cm oieties have been attachedt ov arious chromophores through well-established syntheticr outes.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Aromaticity and Photophysical Behaviour of Ferrocene‐ and Ruthenocene‐Appended Semisynthetic Chlorin Derivatives

Nikkonen

Oliva

Taubert

et al. 2015

Chemistry A European J

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Two novel synthetic strategies to covalently link a metallocene electron-donor unit to a chlorin ring are presented. In one approach, pyropheophorbide a is readily converted into its 13(1) -ferrocenyl dehydro derivative by nucleophilic addition of the ferrocenyl anion to the 13(1) -carbonyl group. In another approach, the corresponding 13(1) -pentamethylruthenocenyl derivative is synthesised from 13(1) -fulvenylchlorin by a facile ligand exchange/deprotonation reaction with the [RuCp*(cod)Cl] (Cp*=pentamethylcyclopentadienyl; cod=1,5-cyclooctadiene) complex. The resulting metallocene-chlorins exhibit reduced aromaticity, which was unequivocally supported by ring-current calculations based on the gauge-including magnetically induced current (GIMIC) method and by calculated nucleus-independent chemical shift (NICS) values. The negative ring current in the isocyclic E ring suggests the antiaromatic character of this moiety and also clarifies the spontaneous reactivity of the complexes with oxygen. The oxidation products were isolated and their electrochemical and photophysical properties were studied. The ruthenocene derivatives turned out to be stable under light irradiation and showed photoinduced charge transfer with charge-separation lifetimes of 152-1029 ps.

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“…Nevertheless, development of a new strategy to prepare ferrocenetype complexes bearing p-extended ligands is still an important subject to be addressed. [5] As a remedy for the weak coordination ability of pextended Cp-type ligands, we had the idea to use a nitrogen-containing aromatic molecule that is isoelectronic to Cp ligands. Tridentate nitrogen ligands with a single negative charge, represented by tris(pyrazolyl)borate (Tp) and related scorpionate ligands, commonly show good coordination abilities.…”

Section: Motoki Toganoh Ayumi Sato and Hiroyuki Furuta*mentioning

confidence: 99%

“…In spite of extensive investigation, a limited number of examples has been reported of isolation and unequivocal characterization of ferrocene-type complexes possessing p-extended Cp-type ligands. [5] As a remedy for the weak coordination ability of pextended Cp-type ligands, we had the idea to use a nitrogen-containing aromatic molecule that is isoelectronic to Cp ligands. [3] Exceptionally, notable success was gained by the aid of nonplanar ligands such as C 70 derivatives and helicene-like ligands.…”

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confidence: 99%

Double‐Decker Ferrocene‐Type Complex of N‐Fused Porphyrin: A Model of π‐Extended Ferrocene?

2011

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Whopper sandwich: A double‐decker ferrocene‐type complex with N‐fused porphyrinato ligands (see picture) was synthesized from N‐fused porphyrin, and its structure and properties were characterized with X‐ray crystallographic analysis, variable‐temperature 1H NMR spectra, and electrochemical measurements. The unique three‐dimensional d–π conjugated system was elucidated with the aid of DFT studies.

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Ferrocene-appended porphyrins: Syntheses and properties

Cited by 119 publications

References 111 publications

Why is Ferrocene so Exceptional?

Why is Ferrocene so Exceptional?

Synthesis, Aromaticity and Photophysical Behaviour of Ferrocene‐ and Ruthenocene‐Appended Semisynthetic Chlorin Derivatives

Double‐Decker Ferrocene‐Type Complex of N‐Fused Porphyrin: A Model of π‐Extended Ferrocene?

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