The Journal of Organic Chemistry · 2015 · 18 citations · 41 references
Natural SciencesChemistryMaterials ScienceInorganic ChemistryOrganic ChemistryHeterocycle SynthesisHeterocyclic ChemistryHeterocyclic CompoundsMacrocycle SynthesisOrganic Electronic MaterialsOrganic SemiconductorsHost ChemistryOptoelectronic PropertiesOrganic ElectronicsQuinoxaline ChemistryQuinoxaline SynthesisSingle-crystal X-ray Diffraction
A series of fully conjugated quinoxaline-based oligophenylene macrocycles is synthesized by Ni(0)-mediated Yamamoto-type diaryl homocoupling of (fluorinated) 2,3-bis(4'-bromophenyl)quinoxaline precursors. Cyclotrimers and cyclotetramers are obtained as the dominant reaction products. The cyclooligomers are fully characterized, including single-crystal X-ray structures, and their optoelectronic properties are analyzed with respect to possible applications in host-guest chemistry and organic electronics.
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