Synthesis and photophysical studies of porphyrin-ferrocene conjugates

Mansour, Hanaa; El‐Khouly, Mohamed E.; Shaban, Shaban Y.; Ito, O.; Jux, Norbert

doi:10.1142/s1088424607000825

Cited by 14 publications

(11 citation statements)

References 6 publications

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“…In comparison, Fcs are also known as classical quenchers of the lowest energy excited states, generally the triplet state 19. 54…”

Section: Resultsmentioning

confidence: 99%

“…[55][56][57] Similarly,( pentamethylcyclopentadienyl)ruthenium p complexes and sitting-atop metalloporphycenes also underwent electron transfer. [54][55][56][57] To the best of our knowledge,t here are no examples in the literatureo faChl derivative attached to any metallocene.…”

Section: Introductionmentioning

confidence: 97%

“…[33,34] Several studies have shown that Fc can effectively quench the singlet excited state of porphyrint hrough photoinduced electron transfer. [18,19,23,54] Moreover,t he groups of Kadish, Fukuzumia nd Sessler studied (pentamethylcyclopentadienyl)ruthenium p complexes of metalloporphyrins and observed photoinduced electron transfer from the Rc unit to the singlet excited state of the metalloporphyrin. [55][56][57] Similarly,( pentamethylcyclopentadienyl)ruthenium p complexes and sitting-atop metalloporphycenes also underwent electron transfer.…”

Section: Introductionmentioning

confidence: 99%

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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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“…In comparison, Fcs are also known as classical quenchers of the lowest energy excited states, generally the triplet state 19. 54…”

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 99%

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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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“…It was also shown that ferrocene quenches porphyrin fluorescence significantly, due to the photo-induced electron transfer from ferrocene to porphyrin [43]. In fact, the quantum yields of porphyrin-ferrocenes are a tenth to a hundred times lower than the tetraphenylporphyrin reference and they decrease with the increase of ferrocene substituents [26,27,44]. For this reason, relatively few studies have been devoted to luminescent electroactive systems including porphyrin-ferrocene conjugates.…”

Section: Resultsmentioning

confidence: 99%

“…The synthesis and the investigation of the porphyrin-ferrocenes physico-chemical properties have received lots of attention in the last decade [26,27]. Porphyrin-ferrocenes were actively applied in photovoltaic light harvesting and energy conversion systems [28–30], and intelligent surface coatings [31,32].…”

Section: Introductionmentioning

confidence: 99%

A Ferrocene-Porphyrin Ligand for Multi-Transduction Chemical Sensor Development

Lvova

Galloni

Floris

et al. 2013

Sensors

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5,10,15,20-Tetraferrocenyl porphyrin, H 2 TFcP, a simple example of a donor-acceptor system, was tested as ligand for the development of a novel multi-transduction chemical sensors aimed at the determination of transition metal ions. The fluorescence energy transfer between ferrocene donor and porphyrin acceptor sub-units was considered. The simultaneously measured optical and potentiometric responses of solvent polymeric membranes based on H 2 TFcP permitted the detection of lead ions in sample solutions, in the concentration range from 2.7 × 10 −7 to 3.0 × 10 −3 M.The detection limit of lead determination was 0.27 μM, low enough to perform the direct analysis of Pb 2+ in natural waters.

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Photoinduced Charge Separation in Zinc–Porphyrin/Tungsten–Alkylidyne Dyads: Generation of Reactive Porphyrin and Metallo Radical States

Moravec

Hopkins

2013

Chemistry A European J

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The luminescent tungsten-alkylidyne metalloligand [WCl(≡C-4,4'-C6H4CC-py)(dppe)2] (1; dppe=1,2-bis(diphenylphosphino)ethane) and the zinc-tetraarylporphyrins ZnTPP and ZnTP(Cl)P (TPP=tetraphenylporphyrin, TP(Cl)P=tetra(p-chlorophenyl)porphyrin) self-assemble in fluorobenzene solution to form the dyads ZnTPP(1) and ZnTP(Cl)P(1), in which the metalloligand is axially coordinated to the porphyrin. Excitation of the porphyrin-centered S1 excited states of these dyads initiates intramolecular energy-transfer (ZnPor→1) and electron-transfer (1→ZnPor) processes, which together efficiently quench the S1 state (~90%). Transient-absorption spectroscopy and an associated kinetic analysis reveal that the net product of the energy-transfer process is the (3)[dπ*] state of coordinated 1, which is formed by S1→(1)[dπ*] singlet-singlet (Förster) energy transfer followed by (1)[dπ*]→(3)[dπ*] intersystem crossing. The data also demonstrate that coordinated 1 reductively quenches the porphyrin S1 state to produce the [ZnPor(-)][1(+)] charge-separated state. This is a rare example of the reductive quenching of zinc porphyrin chromophores. The presence in the [ZnPor(-)][1(+)] charge-separated states of powerfully reducing zinc-porphyrin radical anions, which are capable of sensitizing a wide range of reductive electrocatalysts, and the 1(+) ion, which can initiate the oxidation of H2, produces an integrated photochemical system with the thermodynamic capability of driving photoredox processes that result in the transfer of renewable reducing equivalents instead of the consumption of conventional sacrificial donors.

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Synthesis and photophysical studies of porphyrin-ferrocene conjugates

Cited by 14 publications

References 6 publications

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

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

A Ferrocene-Porphyrin Ligand for Multi-Transduction Chemical Sensor Development

Photoinduced Charge Separation in Zinc–Porphyrin/Tungsten–Alkylidyne Dyads: Generation of Reactive Porphyrin and Metallo Radical States

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