Synthesis Of Fullerene Derivatives Research Articles

Fullerene Building Blocks with Tailor-Made Solubility and New Insights into Their Hierarchical Self-Assembly.

Herein, the synthesis of fullerene derivatives with adjustable polarities and lyotropic aggregation properties is reported. The polarity range spans from superhydrophobic to hydrophilic, while simultaneously providing a further reactive position with a view to graft them onto other materials. The synthetic strategy relies on a selective protection with an isoxazoline moiety. The remaining octahedral positions were further functionalized with the desired groups to tune their solubility, yielding mixed [5:1] hexakisadducts. The subsequent deprotection by clean photolytic reaction led to fullerene pentakisadducts with an incomplete octahedral addition pattern, which are useful forerunners for the synthesis of building blocks. Their hydrophobic/hydrophilic behavior has been characterized both in solution and surface through octanol/water partition coefficients (log P) and contact angle measurements. Furthermore, these derivatives can form supramolecular constructions which have been studied by dynamic light scattering (DLS) and cryo‐TEM.

Synthesis and Characterization of Phenanthrene-substituted Fullerene Derivatives as Electron Acceptors for P3HT-based Polymer Solar Cells

E-mail: dohoonhwang@pusan.ac.krReceived December 3, 2013, Accepted February 6, 20149,10-Bis(bromomethyl)phenanthrene reacted with fullerenes via a Diels-Alder reaction to give phenanthrene-substituted fullerene mono-adducts (PCMA) and bis-adducts (PCBA) as electron acceptors for organicphotovoltaic cells (OPVs). The syntheses of the fullerene derivatives were confirmed by

ChemInform Abstract: Low‐Cost Synthesis of Fullerene Derivatives

Abstractusing refined mixed fullerenes instead of pure C60 as starting material

Low-Cost Synthesis of Fullerene Derivatives

Refined mixed fullerenes were used as a reagent in known organic reactions instead of the pure fullerene C60 with aim to find an alternative, low-cost method for the synthesis of fullerene derivatives potentially exhibiting photoconductive properties. The isolation of C60 or C70 in clean form without admixtures requires the use of large quantities of toluene or other nonpolar solvents, polluting the environment and multiplying the production cost. 1,3-Dipolar cycloaddition of azomethine ylide to fullerite was chosen because this reaction is one of the most widely used for fullerene functionalization, producing material possibly presenting photoinducing behavior. The data showed that the use of the cheaper mixed fullerenes instead of pure C60 leads to the isolation of the same expected products with similar yields. The photoelectric properties of mixed fullerenes and their organic derivatives were also examined. A slightly semiconductive behavior was confirmed as well as a noticeable photoresponse. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications® to view the free supplemental file.

Catalytic Enantioselective Synthesis of Fullerene Derivatives

Catalytic Enantioselective Synthesis of Fullerene Derivatives

Spectral characteristics of an atmospheric-pressure arc discharge during the synthesis of fullerene derivatives

The electron concentration and temperature are measured when elements having various ionization potentials are introduced into the carbon-helium plasma that forms in a high-frequency atmospheric-pressure arc discharge. The effect of the introduced elements on the relative fullerene content in a carbon condensate is also studied. The plasma parameters are determined by in situ emission spectral analysis during the synthesis of fullerene derivatives with scandium, sodium, and silicon. The variation of the atomic and molecular line intensities of the plasma radiation with the distance from the carbon-arc axis is investigated upon the introduction of various doping substances. The optimal temperature conditions for the synthesis of fullerene derivatives with Sc, Na, and Si are found.

Hypervalent Molecular Cluster: C<sub>28</sub>H<sub>4</sub>

A growing number of recent publications on clusters reflect a tremendous interest in these particles. These studies reveal new fundamental physical and chemical aspects of matter. Clusters are called the fifth state of matter: liquid, solid, cluster, gas and plasma. In this work, a carbon cluster was generated by a spark cluster source and detected by single focusing mass spectrometer in situ. We examined the effects of cluster source parameters on the generation of carbon cluster and report our initial results. This method should be useful for studying the mechanism of fullerene formation. In the case when carbon clusters generated in plasma arc are carried by the Ar or H2 gas flow downstream through a vacuum chamber to the ion source of mass spectrometer, we obtained a small binary carbon cluster C28H4 (hydrogenated fullerene). The empty fullerene is tetravalent and strongly binds four hydrogen atoms, which significantly weakens two different sets of bonds and leads to an open-shell electronic structure. Conclusion is that endohedral C28H4 are hypervalent. We have demonstrated how in situ mass spectrometry has led to the rapid development of an important branch of synthetic fullerene chemistry that has yielded many new small fullerenes and related derivatives with novel structures and properties. The impact of mass spectrometry on the synthesis of fullerene derivatives is the subject of this paper. Significantly, a large fraction of products could be condensed on a specially designed collection plate, which allows further spectroscopic characterization of new derivatives.

Synthesis of Fullerene Derivatives with Novel Structures. Liquid—Phase versus Solid—State Reactions

AbstractFor Abstract see ChemInform Abstract in Full Text.

Synthesis of Fullerene Derivatives with Novel Structures-Liquid-Phase versus Solid-State Reactions-

Reactions of C60 with various carbon nucleophiles, particularly those with substituted acetylide and fluorenide ions in the liquid phase, give various C60 derivatives. While the reaction with cyanide salts only affords the cyanated C60 in liquid phase, the solid-state mechanochemical reaction selectively gives the dumbbell-shaped dimer. As typically shown by this example, the solid-state reaction was found to be quite advantageous for the formation of various types of fullerene dimers. The reaction of C60 with phthalazine also results in formation of entirely different products depending on the reaction phase. While the solid-state reaction gives a fullerene dimer incorporated in a bicyclic framework, the liquid-phase thermal reaction affords a derivative of an open-cage fullerene. Utilizing this reaction, an attempt has been made for organic synthesis of endohedral fullerene encapsulating molecular hydrogen through a series of procedures, i.e., opening a hole on the fullerene cage, insertion of molecular hydrogen, and reduction of the size of the opening.

Synthesis of fullerene derivatives

This paper presents the results of plasmochemical synthesis of fullerene derivatives with hydrogen, iodine, iridium, platinum, and scandium. The synthesis is carried out under atmospheric pressure in a carbon-helium plasma stream formed by an ac arc in the rf range.

Synthesis of Fullerene Derivatives for Incorporation in Sol-Gel Glasses

We report on the synthesis of fullerene derivatives containing a trialkoxysilane moiety that exhibit enhanced solubility in solvents commonly used for sol-gel processing. These derivatives have been successfully embedded in glassy bulk samples and thin films that show very promising optical limiting properties.