Synthesis, electrochemistry and photophysical properties of phenylenevinylene fullerodendrimers

Langa, Fernando; Gómez‐Escalonilla, María J.; Dı́ez-Barra, Enrique; Garcı́a-Martı́nez, Joaquín C.; Hoz, Antonio de la; Rodríguez‐López, Julián; González‐Cortés, Araceli; López-Arza, Vicente

doi:10.1016/s0040-4039(01)00484-1

Cited by 53 publications

(23 citation statements)

References 25 publications

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“…[19][20][21][22][23][24] As a further elaboration, electron donors, such as ferrocene etc. have been attached covalently to C 60 -oPPVs and the resulting conjugates have been probed by means of photophysical and electrochemical techniques.…”

Section: Introductionmentioning

confidence: 99%

Tuning the reorganization energy of electron transfer in supramolecular ensembles – metalloporphyrin, oligophenylenevinylenes, and fullerene – and the impact on electron transfer kinetics

et al. 2015

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Oligo(p-phenylenevinylene) (oPPV) wires of various lengths featuring pyridyls at one terminal and C 60 moieties at the other, have been used as molecular building blocks in combination with porphyrins to construct a novel class of electron donor-acceptor architectures. These architectures, which are based on non-covalent, directional interactions between the zinc centers of the porphyrins and the pyridyls, have been characterized by nuclear magnetic resonance spectroscopy and mass spectrometry. Complementary physico-chemical assays focused on the interactions between electron donors and acceptors in the ground and excited states. No appreciable electron interactions were noted in the ground state, which was being probed by electrochemistry, absorption spectroscopy, etc.; the electron acceptors are sufficiently decoupled from the electron donors. In the excited state, a different picture evolved. In particular, steady-state and time-resolved fluorescence and transient absorption measurements revealed substantial electron donor-acceptor interactions. These led, upon photoexcitation of the porphyrins, to tunable intramolecular electron-transfer processes, that is, the oxidation of porphyrin and the reduction of C 60 . In this regard, the largest impact stems from a rather strong distance dependence of the total reorganization energy in stark contrast to the distance independence seen for covalently linked conjugates.

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Section: Introductionmentioning

confidence: 99%

Tuning the reorganization energy of electron transfer in supramolecular ensembles – metalloporphyrin, oligophenylenevinylenes, and fullerene – and the impact on electron transfer kinetics

et al. 2015

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“…Langa et al applied this method to obtain fullerodendrimers (Scheme 23.21) [69]. Dendrimers with oligoarylenes show efficient absorption of light and can act as light-harvesting antennas to give PET processes when they are attached to a suitable acceptor, such as [60]fullerene.…”

Section: Nitrile Iminesmentioning

confidence: 99%

Application of Microwave Irradiation in Carbon Nanostructures

Langa

Cruz

2012

Microwaves in Organic Synthesis

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Fullerenes Under Microwave Irradiation IntroductionSince Krätschmer and co-workers discovered a procedure for the preparation of bulk quantities of C 60 [1] in the early 1990s, the physical properties of fullerenes have been intensively investigated. However, members of this new family of compounds are insoluble or sparingly soluble in most solvents [2] and, consequently, C 60 is difficult to handle. Chemical functionalization allows the preparation of soluble C 60 derivatives that maintain the electronic properties of fullerenes. For this reason, the chemistry and derivatization of fullerenes has continued to attract attention aimed at preparing derivatives with interesting physical properties and biological activities [3]. New materials based on C 60 derivatives have shown promise in the fields of material science [4], solar energy conversion [5], nonlinear optical behavior [6], superconductivity [7], ferromagnetism [8], medicinal chemistry [9], and HIV-1 protease inhibition [10].Among the suitable procedures for the functionalization of fullerenes (Scheme 23.1) [11], cycloadditions provide a powerful tool as C 60 behaves as an electron-deficient olefin with a relatively low-lying LUMO (−3.14 eV) [12,13].As a consequence, a large variety of cycloaddition reactions have been carried out [12, 14] in which C 60 (1) is the reactive 2π component. In this context, [1 + 2]-, [2 + 2]-, [3 + 2]-, and [4 + 2]-cycloadditions have all been performed (Scheme 23.2) and the conditions for cycloadduct formation depend strongly on the gap between the controlling orbitals. For this reason, it is frequently necessary to use harsh conditions involving several hours (or days) under reflux in high-boiling solvents. As microwave irradiation has been successfully used in cycloaddition reactions solving problems concerning reversibility and decomposition of reagents and/or products, it was evident to use this methodology in fullerene chemistry as most fullerene derivatives are prepared by Diels-Alder [15] or 1,3-dipolar cycloaddition reactions [16].Microwaves in Organic Synthesis, Third Edition.

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“…[101][102][103] A study on the thermal stabilities of pyrazolino [60]fullerenes has recently been reported. [104] …”

Section: Cycloadditions Of Azomethine Imines and Nitrile Iminesmentioning

confidence: 99%

Microwave‐Assisted 1,3‐Dipolar Cycloaddition: an Eco‐Friendly Approach to Five‐Membered Heterocycles

Piñeiro

Melo

2009

Eur J Org Chem

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The review describes the use of microwave technology to carry out 1,3-dipolar cycloaddition reactions, an important tool for the construction of five-membered heterocycles. Microwave methodology can be applied to generate 1,3-dipoles (nitrones, nitrile oxides, azomethine ylides, azomethine imines, nitrile imines, azides, carbonyl ylides) and to promote the subsequent cycloaddition and usually avoids harsh reaction conditions. This nonconventional energy source is able

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Synthesis, electrochemistry and photophysical properties of phenylenevinylene fullerodendrimers

Cited by 53 publications

References 25 publications

Tuning the reorganization energy of electron transfer in supramolecular ensembles – metalloporphyrin, oligophenylenevinylenes, and fullerene – and the impact on electron transfer kinetics

Tuning the reorganization energy of electron transfer in supramolecular ensembles – metalloporphyrin, oligophenylenevinylenes, and fullerene – and the impact on electron transfer kinetics

Application of Microwave Irradiation in Carbon Nanostructures

Microwave‐Assisted 1,3‐Dipolar Cycloaddition: an Eco‐Friendly Approach to Five‐Membered Heterocycles

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