Trans-Substituted porphyrin building blocks bearing iodo and ethynyl groups for applications in bioorganic and materials chemistry

Ravikanth, Mangalampalli; Strachan, Jon‐Paul; Li, Feirong; Lindsey, Jonathan S.

doi:10.1016/s0040-4020(98)00408-6

Cited by 56 publications

(51 citation statements)

References 26 publications

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“…Compound 6 was previously synthesised from commercially available 4-iodobenzaldehyde (5) in one step. [23] Similar conditions were used to remove the bromine atom with trimethylsilylacetylene. However, the target product was not obtained in any case.…”

Section: Resultsmentioning

confidence: 99%

p‐Phenyleneethynylene Molecular Wires: Influence of Structure on Photoinduced Electron‐Transfer Properties

Wielopolski

Atienza

Clark

et al. 2008

Chemistry A European J

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A series of donor-acceptor arrays (exTTF-oPPE-C60) containing pi-conjugated oligo(phenyleneethynylene) wires (oPPE) of different length between pi-extended tetrathiafulvalene (exTTF) as electron donor and fullerene (C60) as electron acceptor has been prepared by following a convergent synthesis. The key reaction in these approaches is the bromo-iodo selectivity of the Hagihara-Sonogashira reaction and the deprotecting of acetylenes with different silyl groups to afford the corresponding donor-acceptor conjugates in moderate yields. The electronic interactions between the three electroactive species were determined by using UV-visible spectroscopy and cyclic voltammetry. Our studies clearly confirm that, although the C60 units are connected to the exTTF donor through pi-conjugated oPPE frameworks, no significant electronic interactions are observed in the ground state. Theoretical calculations predict how a simple exchange from C=C double bonds (i.e., oligo(p-phenylenevinylene) to C triple chemical bond C triple bonds (i.e., oPPE) in the electron donor-acceptor conjugates considerably alters long-range electron transfer. Photoexcitation of exTTF-oPPE-C60 leads to the following features: a transient photoproduct with maxima at 660 and 1000 nm, which are unambiguously attributed to the photolytically generated radical-ion-pair state, [exTTF*+-oPPE-C60*]. Both charge-separation and charge-recombination processes give rise to a molecular-wire behaviour of the oPPE moiety with an attenuation factor (beta) of (0.2+/-0.05) A(-1).

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Section: Resultsmentioning

confidence: 99%

p‐Phenyleneethynylene Molecular Wires: Influence of Structure on Photoinduced Electron‐Transfer Properties

Wielopolski

Atienza

Clark

et al. 2008

Chemistry A European J

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“…Diiodo-substituted phthalocyanine 2 and 4-ethynylbenzaldehyde were prepared according to published procedures. [8,9] Photophysics: Steady-state fluorescence measurements were performed using a Fluoromax 3 (Horiba Jobin Yvon) instrument. Transient absorption experiments (based on nanosecond laser photolysis) were performed with the output of the third harmonics (i.e., 355 nm) of a Nd:YAG laser (Quanta-Ray GCR-11, Spectra Physics).…”

Section: Methodsmentioning

confidence: 99%

“…The synthesis of 3 was carried out starting from the diiodophthalocyanine precursor 2 [8] by means of Sonogashira cross-coupling reactions with 4-ethynylbenzaldehyde [9] in the presence of Et 3 N, THF, and a catalytic amount of [PdA C H T U N G T R E N N U N G (PPh 3 ) 2 Cl 2 ] and CuI, affording 3 in 58 % yield. Dimer 3 was finally subjected to a 1,3-dipolar cycloaddition with C 60 and sarcosine in refluxing toluene to give 1 in 21 % yield after purification by column chromatography on silica gel using toluene/ethyl acetate mixtures as eluent.…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

A Bis(C₆₀)–Bis(phthalocyanine) Nanoconjugate: Synthesis and Photoinduced Charge Transfer

et al. 2008

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A novel dimeric phthalocyanine-C60 nanoconjugate, consisting of a bisphthalocyanine core to which two fullerenes are attached, has been prepared. The synthetic strategy implemented the preparation of a diformyl butadiynyl-bridged bisphthalocynaninato-zinc(II) complex by means of palladium-catalyzed cross-coupling reactions and subsequent dipolar cycloaddition reactions. Photophysical experiments confirm that an intramolecular electron transfer, namely, from the photoexcited ZnPc moiety to the electron-accepting C60 unit, governs the overall photoreactivity of the nanoconjugate. Through-space charge-transfer interactions facilitated by the close proximity of the ZnPc and the C60 moieties play a decisive role in determining the lifetimes of the charge-separated state which range from 10(-10) to 10(-9) seconds.

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“…The porphyrins 6-8 were synthesized using Lindsey's method [47] by the reaction of aldehydes 1-3 and dipyrromethanes 4,5 in the presence of a catalytic amount of boron trifluoride-etherate complex with subsequent DDQ oxidation (Scheme 1). Compound 7 was identical in measured parameters to that described in the literature [35].…”

Section: Resultsmentioning

confidence: 99%

Design and studies of novel polyoxysterol-based porphyrin conjugates

et al. 2012

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a b s t r a c tNew types of steroid-porphyrin conjugates derived from 20-hydroxyecdysone (20E) and 24-epibrassinolide (EBl) were synthesized. An exceptional regioselectivity in the reaction of both steroids with porphyrin boronic acids was found to give side-chain-conjugated boronic esters as sole products. UV-Vis-, fluorescence and NMR spectroscopy yielded similar data for all the studied compounds confirming the solvent driven supramolecular assembly with formation of J-aggregates. CD measurements of water diluted solutions showed a clear difference between 20E and EBl conjugates. The latter showed a strong supramolecular chirality, whereas 20E J-aggregates did not.

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Trans-Substituted porphyrin building blocks bearing iodo and ethynyl groups for applications in bioorganic and materials chemistry

Cited by 56 publications

References 26 publications

p‐Phenyleneethynylene Molecular Wires: Influence of Structure on Photoinduced Electron‐Transfer Properties

p‐Phenyleneethynylene Molecular Wires: Influence of Structure on Photoinduced Electron‐Transfer Properties

A Bis(C₆₀)–Bis(phthalocyanine) Nanoconjugate: Synthesis and Photoinduced Charge Transfer

Design and studies of novel polyoxysterol-based porphyrin conjugates

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Trans-Substituted porphyrin building blocks bearing iodo and ethynyl groups for applications in bioorganic and materials chemistry

Cited by 56 publications

References 26 publications

p‐Phenyleneethynylene Molecular Wires: Influence of Structure on Photoinduced Electron‐Transfer Properties

p‐Phenyleneethynylene Molecular Wires: Influence of Structure on Photoinduced Electron‐Transfer Properties

A Bis(C60)–Bis(phthalocyanine) Nanoconjugate: Synthesis and Photoinduced Charge Transfer

Design and studies of novel polyoxysterol-based porphyrin conjugates

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A Bis(C₆₀)–Bis(phthalocyanine) Nanoconjugate: Synthesis and Photoinduced Charge Transfer