Photoinduced electron transfer in a clicked fullerene–porphyrin conjugate

Iehl, Julien; Vartanian, Maida; Holler, Michel; Nierengarten, Jean‐François; Delavaux‐Nicot, Béatrice; Strub, Jean‐Marc; Dorsselaer, Alain Van; Wu, Yilei; Mohanraj, John; Yoosaf, K.; Armaroli, Nicola

doi:10.1039/c0jm02310h

Cited by 51 publications

(77 citation statements)

References 89 publications

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“…The latter corresponds to the hydrolysis of a malonic ester unit followed by a decarboxylation, leading to a loss of C 14 H 22 N 3 O 9 with respect to the parent peak. [32] Despite the high level of fragmentation observed in the MALDI-TOF spectrum of C 60 (C) 12 , no significant signals corresponding to defected products could be observed thus providing definitive conclusion about the monodispersity of the isolated product as already suggested from its IR spectrum in which no azide residues could be detected.…”

mentioning

confidence: 73%

The Inhibition of Liposaccharide Heptosyltransferase WaaC with Multivalent Glycosylated Fullerenes: A New Mode of Glycosyltransferase Inhibition

Durka

Buffet

Iehl

et al. 2011

Chemistry A European J

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L,D-Heptosides (L-glycero-D-manno-heptopyranoses) are found in important bacterial glycolipids such as lipopolysaccharide (LPS), the biosynthesis of which is targeted for the development of novel antibacterial agents. This work describes the synthesis of a series of fullerene hexa-adducts bearing 12 copies of peripheral sugars displaying the mannopyranose core structure of bacterial L,D-heptoside. The multimers were assembled through an efficient copper-catalyzed alkyne-azide cycloaddition reaction as the final step. The final fullerene sugar balls were assayed as inhibitors of heptosyltransferase WaaC, the glycosyltransferase catalyzing the incorporation of the first L-heptose into LPS. Interestingly, the inhibition of the final molecules was found in the low micromolar range (IC(50) =7-45 μM), whereas the corresponding monomeric glycosides displayed high micromolar to low millimolar inhibition levels (IC(50) always above 400 μM). When evaluated on a "per-sugar" basis, these inhibition data showed that, in each case, the average affinity of a single glycoside of the fullerenes towards WaaC was significantly enhanced when displayed as a multimer, thus demonstrating an unexpected multivalent effect. To date, such a multivalent mode of inhibition had never been evidenced with glycosyltransferases.

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confidence: 73%

The Inhibition of Liposaccharide Heptosyltransferase WaaC with Multivalent Glycosylated Fullerenes: A New Mode of Glycosyltransferase Inhibition

Durka

Buffet

Iehl

et al. 2011

Chemistry A European J

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100

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“…Additional cyclic and square wave voltammograms for 1 and a porphyrinic analog are provided in Supporting Information. [19]. This value ensures that recombination lies in the inverted region since reorganization energies were measured to be much less than 1 eV [5b].…”

Section: Electrochemistry In Solutionmentioning

confidence: 99%

Electron Transfer Rates in an Adsorbed C₆₀‐Porphyrin Dyad

Fortgang¹,

Urbani²,

Holler³

et al. 2015

Electroanalysis

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Association of C60 and porphyrin entities to build light harvesting systems is a promising alternative for future photovoltaic devices. Herein, we determine the electron transfer rates in a C60‐porphyrin dyad anchored onto a gold ultramicroelectrode via the porphyrin core. Similar rates are observed for both redox entities, suggesting a tilt of the molecules allowing an efficient through‐space communication between C60 and the electrode.

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“…[17,37] The electrochemical and photophysical properties of this multicomponent system have been investigated in detail. [37] In benzonitrile, compound 38 undergoes photoinduced electron transfer and the resulting charge-separated state is relatively long lived (τ=0.48 μs). In contrast, intramolecular energy transfer has been evidenced in toluene, with the generation of the fullerene triplet level upon selective excitation of the porphyrin moiety.…”

Section: Clicked Fullerene-porphyrin Conjugatesmentioning

confidence: 99%

“…Among them, a few examples have been prepared from clickable fullerene building blocks. [17,[36][37][38] Typical examples are shown in Figures 1 and 2.…”

Section: Clicked Fullerene-porphyrin Conjugatesmentioning

confidence: 99%

The Impact of Copper‐Catalyzed Alkyne–Azide 1,3‐Dipolar Cycloaddition in Fullerene Chemistry

Nierengarten

2014

The Chemical Record

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Click reactions largely cross the borders of organic synthetic chemistry and are now at the forefront of many interdisciplinary studies at the interfaces between chemistry, physics, and biology. As part of this research, our group is involved in a program on the development of clickable fullerene building blocks and their application in the preparation of a large variety of new advanced materials and bioactive compounds. Importantly, the introduction of the click chemistry concept in fullerene chemistry allowed us to produce compounds that would barely be accessible by using the classical tools of fullerene chemistry. This is particularly the case for the conjugation of fullerenes with other carbon nanoforms, such as carbon nanohorns and graphene. It is also the case for most of the sophisticated molecular ensembles constructed from clickable fullerene hexa-adduct building blocks. In this paper, we have summarized our ongoing progress in this particular field.

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Photoinduced electron transfer in a clicked fullerene–porphyrin conjugate

Cited by 51 publications

References 89 publications

The Inhibition of Liposaccharide Heptosyltransferase WaaC with Multivalent Glycosylated Fullerenes: A New Mode of Glycosyltransferase Inhibition

The Inhibition of Liposaccharide Heptosyltransferase WaaC with Multivalent Glycosylated Fullerenes: A New Mode of Glycosyltransferase Inhibition

Electron Transfer Rates in an Adsorbed C₆₀‐Porphyrin Dyad

The Impact of Copper‐Catalyzed Alkyne–Azide 1,3‐Dipolar Cycloaddition in Fullerene Chemistry

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Photoinduced electron transfer in a clicked fullerene–porphyrin conjugate

Cited by 51 publications

References 89 publications

The Inhibition of Liposaccharide Heptosyltransferase WaaC with Multivalent Glycosylated Fullerenes: A New Mode of Glycosyltransferase Inhibition

The Inhibition of Liposaccharide Heptosyltransferase WaaC with Multivalent Glycosylated Fullerenes: A New Mode of Glycosyltransferase Inhibition

Electron Transfer Rates in an Adsorbed C60‐Porphyrin Dyad

The Impact of Copper‐Catalyzed Alkyne–Azide 1,3‐Dipolar Cycloaddition in Fullerene Chemistry

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Electron Transfer Rates in an Adsorbed C₆₀‐Porphyrin Dyad