Y. Fogel, L. Zhi, Ali Rouhanipour
Aug 28, 2009
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Quality indicators
Journal
Macromolecules
Abstract
A novel homologous series of five monodisperse ribbon-type polyphenylenes, with rigid dibenzo[e,l]pyrene cores in the repeat units, are synthesized by a microwave-assisted Diels−Alder reaction. The size of the obtained polyphenylene ribbons ranges from 132 to 372 carbon atoms in the aromatic backbone which incorporates up to six dibenzo[e,l]pyrene units, thus showing quite different aspect ratios. Because of the flexibility of the backbone and the peripheral substitution with dodecyl chains, the polyphenylene ribbons are well soluble in organic solvents and can be fully characterized by standard analytical techniques. Their unique structure is especially designed to produce a series of giant ribbon-type polycyclic aromatic hydrocarbons (PAHs) in a single further reaction step by cyclodehydrogenation. Therefore, the incorporated dibenzo[e,l]pyrene cores are an important feature because they facilitate the dehydrogenation and improve the reaction yields. The smallest representative of the completely dehydro...