ChemInform Abstract: Elements for a Rational Polymer Approach Towards Carbon Nanostructures

École Polytechnique Fédérale de Lausanne, Institute of Materials, EPFL - STI - IMX - LMOM, MXG 037, Station 12, 1015 Lausanne, Switzerland.
Angewandte Chemie International Edition (Impact Factor: 11.26). 07/2012; 51(27):6569-71. DOI: 10.1002/anie.201201423
Source: PubMed


Growth spurt: A recent series of publications promises to pave the way for a polymer approach towards well-defined carbon nanostructures by combining the stepwise organic synthesis of carbon nanotube (CNT) end caps and their use as templates for CNT growth by Diels-Alder addition of nitroethylene as a masked acetylene derivative.

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    ABSTRACT: Since the first successful synthesis in 2008, methods to prepare the [n]cycloparaphenylenes have evolved rapidly. The aim of this synopsis is to provide an overview of recent advancements in this emerging field. The optoelectronic properties and supramolecular chemistry of these unique structures are presented as well.
    The Journal of Organic Chemistry 11/2012; 77(23). DOI:10.1021/jo302186h · 4.72 Impact Factor
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    ABSTRACT: Two novel arene-bridged cycloparaphenylene dimers (1 and 2) were prepared using a functionalized precursor, bromo-substituted macrocycle 7. The preferred conformations of these dimeric structures were evaluated computationally in the solid-state, as well as in the gas and solution phases. In the solid-state, the "trans" configuration of 1 is preferred by 34 kcal/mol due to the denser crystal packing structure that is achieved. In contrast, in the gas phase and in solution, the "cis" conformation is favored by 7 kcal/mol (dimer 1) and 10 kcal/mol (dimer 2), with a "cis" to "trans" activation barrier of 20 kcal/mol. The stabilization seen in the "cis" conformations is attributed to the increased van der Waals interactions between the two cycloparaphenylene rings. These calculations indicate that that the "cis" conformation is accessible in solution, which is promising for future efforts towards the synthesis of short carbon nanotubes (CNTs) via cycloparaphenylene monomers. In addition, the optoelectronic properties of these dimeric cycloparaphenylenes were characterized both experimentally and computationally for the first time.
    Journal of the American Chemical Society 11/2012; 134(48). DOI:10.1021/ja307373r · 12.11 Impact Factor
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    ABSTRACT: To meet the ever growing demand for carbon nanomaterials with tailored properties, Diels–Alder reactions are emerging as an efficient alternative to other synthetic methods. From an application perspective, the development of convenient surface functionalization strategies for carbon nanostructures is of paramount importance. Pristine carbon nanostructures display a natural tendency to undergo Diels–Alder reactions with a range of functional dienes and dienophiles without the need of a catalyst. This has sparked significant scientific interest in exploiting the Diels–Alder reaction as a powerful strategy for their synthesis as well as for their subsequent surface functionalization. The present review highlights the remarkable role of Diels–Alder reactions for the synthesis of fullerenes, carbon nanotubes and graphene, and its promise as a facile carbon nanostructure functionalization strategy with small molecules and polymer chains. A critical overview of the recent developments evidencing the potential of Diels–Alder reactions as an efficient route to carbon based functional materials is presented.
    04/2013; 4(15):-. DOI:10.1039/C3PY00232B
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