Scalable synthesis of [8]cycloparaphenyleneacetylene carbon nanohoop using alkyne metathesis
Xin Zhou, Hyejin Kwon, Richard R. Thompson, Robert J. Herman, Frank R. Fronczek, Carson J. Bruns, Semin Lee
Abstract
-stilbene-based building block is subjected to alkyne metathesis macrocylization. The following sequence of alkene-selective bromination and dehydrobromination afforded a [8]cycloparaphenyleneacetylene derivative in high yield with good scalability. X-Ray crystal structure and computational analysis revealed a unique same-rim conformation for the eight methyl groups on the nanohoop.
Topics & Concepts
AlkyneAromatizationAlkeneMetathesisHalogenationYield (engineering)ChemistryScalabilityCombinatorial chemistryDerivative (finance)Organic chemistryMaterials scienceCatalysisComputer scienceDatabasePolymerizationFinancial economicsMetallurgyEconomicsPolymerSynthesis and Properties of Aromatic CompoundsSynthetic Organic Chemistry MethodsPolydiacetylene-based materials and applications