Various Synthetic Routes to a Gable‐Like Bis(porphyrin) Constructed on a 1,10‐Phenanthroline Chelate

Beyler, Maryline; Beemelmanns, Christine; Heitz, Valérie; Sauvage, Jean‐Pierre

doi:10.1002/ejoc.200900149

Cited by 11 publications

(12 citation statements)

References 36 publications

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“…Materials: All solvents and chemicals were of reagent-grade quality, purchased, and used without further purification. 4-Iodobenzenediazonium tetrafluoroborate, [23] 5-(pinacolboryl)-10,15,20-tris(3,5-di-tert-butylphenyl)porphyrinatozinc(II), [35] and 5-phenyl-10,15,20-tris(3,5-di-tert-butylphenyl)porphyrinatozinc(II) [36] (ZnP-ref) were prepared according to the reported procedures. An optically transparent fluorine-doped tin oxide electrode (denoted as FTO; AGC Fabritech) was washed by sonication in 2-propanol and cleaned in an O 3 atmosphere in advance.…”

Section: Methodsmentioning

confidence: 99%

Preparation and Photophysical and Photoelectrochemical Properties of a Covalently Fixed Porphyrin–Chemically Converted Graphene Composite

Umeyama

Mihara

Tezuka

et al. 2012

Chemistry A European J

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Chemically converted graphene (CCG) covalently linked with porphyrins has been prepared by a Suzuki coupling reaction between iodophenyl-functionalized CCG and porphyrin boronic ester. The covalently linked CCG-porphyrin composite was designed to possess a short, rigid phenylene spacer between the porphyrin and the CCG. The composite material formed stable dispersions in DMF and the structure was characterized by spectroscopic, thermal, and microscopic measurements. In steady-state photoluminescence spectra, the emission from the porphyrin linked to the CCG was quenched strongly relative to that of the porphyrin reference. Fluorescence lifetime and femtosecond transient absorption measurements of the porphyrin-linked CCG revealed a short-lived porphyrin singlet excited state (38 ps) without yielding the porphyrin radical cation, thereby substantiating the occurrence of energy transfer from the porphyrin excited state to the CCG and subsequent rapid decay of the CCG excited state to the ground state. Consistently, the photocurrent action spectrum of a photoelectrochemical device with a SnO(2) electrode coated with the porphyrin-linked CCG exhibited no photocurrent response from the porphyrin absorption. The results obtained here provide deep insight into the interaction between graphenes and π-conjugated systems in the excited and ground states.

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Section: Methodsmentioning

confidence: 99%

Preparation and Photophysical and Photoelectrochemical Properties of a Covalently Fixed Porphyrin–Chemically Converted Graphene Composite

Umeyama

Mihara

Tezuka

et al. 2012

Chemistry A European J

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“…Details on the preparation of the complexes and characterization of association parameters have been reported previously 28. 48 Absorption spectra were recorded by using a Perkin–Elmer Lambda 9 spectrophotometer and emission spectra, uncorrected if not otherwise specified, were detected by using a Spex Fluorolog II spectrofluorimeter equipped with a Hamamatsu R928 photomultiplier. Luminescence quantum yields were evaluated from the area of the luminescence spectra, corrected for the photomultiplier response, with reference to TPP (5,10,15,20‐tetraphenyl‐porphyrin) in aerated toluene ( Φ fl =0.11) 49.…”

Section: Methodsmentioning

confidence: 99%

Unusual Photoinduced Electron Transfer from a Zinc Porphyrin to a Tetrapyridyl Free‐Base Porphyrin in a Noncovalent Multiporphyrin Array

Ventura

Flamigni

Beyler

et al. 2010

Chemistry A European J

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Excitation of the peripheral Zn porphyrin units in a noncovalent five-porphyrin array, formed by gable-like zinc(II) bisporphyrins and a central free-base meso-tetrakis(4-pyridyl)porphyrin in a 2:1 ratio, (ZnP(2))(2).(TPyP), does not lead to a quantitative sensitization of the luminescence of the free-base porphyrin acceptor, even though there is an effective energy transfer. Time resolution of the luminescence evidences a quenching of TPyP upon sensitization by the peripheral ZnP(2). The time evolution of the TPyP fluorescence in the complex can be described by a bi-exponential fitting with a major component of 180 ps and a minor one of 5 ns, compared to an isolated TPyP lifetime of 9.4 ns. The two quenched lifetimes are shown to be correlated to the presence of 2:1 and 1:1 complexes, respectively. No quenching of TPyP fluorescence occurs in (ZnP(2))(2).(TPyP) at 77 K in a rigid solvent for which only an energy-transfer process (tau=150+/-10 ps) from peripheral ZnP(2) to the central TPyP is observed. An unusual HOMO-HOMO electron-transfer reaction from ZnP(2) to the excited TPyP units, responsible for the observed phenomena, is detected. The resulting charge-separated state, (ZnP(2))(+)(2).(TPyP)(-) is found to recombine to the ground state with a lifetime of 11 ns.

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“…11 coupling reactions and allowing more efficient yields were reported. 12 Both dipyridyl-incorporating chelates 2 and 3 were obtained thanks to a double-Suzuki cross-coupling reaction.…”

Section: Resultsmentioning

confidence: 99%

Coordination Chemistry-Assembled Porphyrinic Catenanes

2010

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Non covalent [2]catenanes were synthesized in high yield as kinetic products or as thermodynamic products after completion of an equilibrium. These sophisticated architectures were assembled in two steps, from an oblique bis-zinc(II) porphyrin and two different dipyridyl chelates, by using Cu(I)-N interactions to assemble acyclic complexes and Zn(II)-N interactions to generate rings. (1)H NMR including 2D COSY and ROESY experiments were used to characterize each compound. Spectrophotometric titrations highlight the influence of geometry in terms of distances and angles in non covalent coordinated assemblies. In fact, it was proved that a perfect fit leads to highly stable coordination chemistry-assembled species.

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Various Synthetic Routes to a Gable‐Like Bis(porphyrin) Constructed on a 1,10‐Phenanthroline Chelate

Cited by 11 publications

References 36 publications

Preparation and Photophysical and Photoelectrochemical Properties of a Covalently Fixed Porphyrin–Chemically Converted Graphene Composite

Preparation and Photophysical and Photoelectrochemical Properties of a Covalently Fixed Porphyrin–Chemically Converted Graphene Composite

Unusual Photoinduced Electron Transfer from a Zinc Porphyrin to a Tetrapyridyl Free‐Base Porphyrin in a Noncovalent Multiporphyrin Array

Coordination Chemistry-Assembled Porphyrinic Catenanes

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