Organofullerene Materials

Tagmatarchis, Nikos; Prato, Maurizio

doi:10.1007/b94377

Cited by 16 publications

(10 citation statements)

References 288 publications

(326 reference statements)

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“…In addition, these results are also consistent with the current understanding of the electron affinity of fullerenes. Fullerenes are widely known to have a very high electron affinity, as they are capable of accepting at least 6 electrons upon reduction (i.e., act as an electron acceptor). − The detection of C 60 2– , C 60 3– , C 60 4– , C 60 5– , and C 60 6– ions electrochemically provides experimental evidence of the triple degeneracy of the lowest unoccupied molecular orbital (LUMO) of fullerene . Similarly, theoretical and experimental results show that the oxidation (i.e., donation of an electron) of C 60 is more challenging .…”

Section: Resultsmentioning

confidence: 98%

Controlling Non-Covalent Interactions to Modulate the Dispersion of Fullerenes in Polymer Nanocomposites

et al. 2011

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Polymer nanocomposites (PNCs) are materials based on a class of filled plastics that contain relatively small amounts of nanoparticles, which can impart improved structural, mechanical, and thermal properties relative to the neat polymer. However, the homogeneous dispersion of the nanoparticles into a polymer matrix is critical and an impeding factor for the controlled enhancement of PNC properties. In this work, we provide new insight into the importance of polymer chain connectivity and nanoparticle shape and curvature on the formation of noncovalent electron donor–acceptor (EDA) interactions between polymers and nanoparticles. This is accomplished by experimentally monitoring the dispersion of nanoparticles in copolymers containing varying amounts of functional moieties that can form noncovalent interactions with carbon nanoparticles with corroboration through density functional calculations. The results show that the presence of a minority of interacting functional groups within a polymer chain leads to an optimum interaction between the polymer and fullerene. Density functional theory calculations that identify the binding energy and geometry of the interaction between the functional monomers and fullerenes correspond very well with the experimental results. Moreover, comparison of these results to similar studies with single-walled carbon nanotubes (SWNT) indicate a distinct difference in the ability of EDA interactions to improve the dispersion of fullerenes relative to their impact on SWNT. Thus, the polymer chain connectivity, the polymer chain conformation, and size and shape of the nanoparticle modulate the formation of intermolecular interactions and directly impact the dispersion of the resultant nanocomposite.

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Section: Resultsmentioning

confidence: 98%

Controlling Non-Covalent Interactions to Modulate the Dispersion of Fullerenes in Polymer Nanocomposites

et al. 2011

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“…11,12 Among the various fullerene derivatives that have been reported in the literature, fulleropyrrolidines, such as N-methyl-3,4-fulleropyrrolidine (NMFP), play an important role in designing new fullerene derivatives and biologically active compounds. [13][14][15][16][17][18][19] In particular, the NMFP derivatives have attracted significant attention for chemists, and they are widely used in photo-electronic applications and photovoltaic devices. [20][21][22][23][24][25][26][27] In contrast to the experimental results for metal-free dye sensitizers, the theoretical investigations of these compounds are still relatively limited.…”

Section: Introductionmentioning

confidence: 99%

Photo‐physical Properties of N‐methyl‐3,4‐fulleropyrrolidine and Its Derivatives: A DFT and TD‐DFT Investigation

Tai¹,

Hsieh²,

Yeh³

et al. 2012

J Chinese Chemical Soc

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A series of N-methyl-3,4-fulleropyrrolidine (NMFP) derivatives were designed by selecting different pconjugated linkers and electron-donating groups as D-p-A and D-A systems. The optimised structures and photo-physical properties of NMFP and its derivatives have been determined using density functional theory (DFT) and time-dependent density functional theory (TD-DFT) methods with the B3LYP functional and the 6-31G basis set. According to the computation analysis, both the p-conjugated linkers and the electron-donating groups can influence the electronic and photo-physical properties of the NMFP derivatives. Our calculated results demonstrated that the electron-donating groups, with significant electron-donating ability, had the tendency to increase the highest occupied molecular orbital (HOMO) energy. The p-conjugated linkers with lower resonance energy decreased the lowest occupied molecular orbital (LUMO) energy and caused a significant decrease in the energy gap (E g ) between the E HOMO and E LUMO . A Natural Bond Orbital (NBO) analysis examines the effect of the electron-donating group, p conjugated linker, and electron-withdrawing group for these NMFP derivatives. For the NMFP derivatives, a projected density of state (PDOS) analysis demonstrated that the electron density of HOMO and LUMO are concentrated on the electron-donating group and the p-conjugated linker, respectively. A TD-DFT/ B3LYP calculation was performed to calculate the electronic absorption spectra of these NMFP derivatives. Both the electron-donating group and the p-conjugated linker contribute to the major absorption peaks, which are assigned as HOMO to LUMO transitions and are red-shifted relative to those of non-substituted NMFP. CHEMICAL SOCIETY* r and a were defined as the bond length (bond angle) between the C atom of pyrrolidine moiety (NMFP) and substituted group and the calculated E HOMO and E LUMO values of NMFP are -5.850 and -3.212 eV, respectively.

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“…However, the activation of the C 60 –H bond is still in its infancy and is achieved mainly with the utilization of strong bases by taking advantage of the acidic property of the fullerenyl H atom due to the strong electron deficiency of C 60 . Considering the diversity of the protocols that have been developed for C–H activations during the past several decades and the promising potential of organofullerenes for various applications, it is of both interest and importance to explore new methodologies for the activation of C 60 –H bond, which has a relative low bond dissociation energy of about 70 kcal/mol. , …”

Section: Introductionmentioning

confidence: 99%

Formation of Singly Bonded PhCH₂C₆₀–C₆₀CH₂Ph Dimers from 1,2-(PhCH₂)HC₆₀ via Electroreductive C₆₀–H Activation

Yang

Gao

2011

J. Org. Chem.

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Organofullerene Materials

Cited by 16 publications

References 288 publications

Controlling Non-Covalent Interactions to Modulate the Dispersion of Fullerenes in Polymer Nanocomposites

Controlling Non-Covalent Interactions to Modulate the Dispersion of Fullerenes in Polymer Nanocomposites

Photo‐physical Properties of N‐methyl‐3,4‐fulleropyrrolidine and Its Derivatives: A DFT and TD‐DFT Investigation

Formation of Singly Bonded PhCH₂C₆₀–C₆₀CH₂Ph Dimers from 1,2-(PhCH₂)HC₆₀ via Electroreductive C₆₀–H Activation

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Organofullerene Materials

Cited by 16 publications

References 288 publications

Controlling Non-Covalent Interactions to Modulate the Dispersion of Fullerenes in Polymer Nanocomposites

Controlling Non-Covalent Interactions to Modulate the Dispersion of Fullerenes in Polymer Nanocomposites

Photo‐physical Properties of N‐methyl‐3,4‐fulleropyrrolidine and Its Derivatives: A DFT and TD‐DFT Investigation

Formation of Singly Bonded PhCH2C60–C60CH2Ph Dimers from 1,2-(PhCH2)HC60 via Electroreductive C60–H Activation

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Formation of Singly Bonded PhCH₂C₆₀–C₆₀CH₂Ph Dimers from 1,2-(PhCH₂)HC₆₀ via Electroreductive C₆₀–H Activation