Organic Letters · 2022 · 15 citations · 33 references
Natural SciencesChemistryMaterials ScienceEnergy MaterialsMaterials ChemistrySemiconductor MaterialsOrganic Electronic MaterialsOrganic SemiconductorsPerovskite MaterialsPhotovoltaic MaterialsSolar Cell MaterialsSolar CellsHeterocycle FunctionalizationOrganic Photovoltaic MaterialsOrganic PhotovoltaicsOrganic Solar CellsOrganic-inorganic Hybrid PerovskitesPerovskite Solar CellsPyrazine ChemistrySelectivity
Repeated tandem electro-oxidative C–C and C–N coupling and aromatization were employed for the efficient construction of aza[7]helicene (BA7) as a key intermediate and the targeted pyrazine-fused bis-aza[7]helicene (PBBA7) derivatives in 90.0–93.2% isolated yields under a controlled potential. The electrosynthetic protocol showed high selectivity and enabled rapid access to functionalized organic conjugated materials from readily available polycyclic aromatic amines. A synthetic mechanistic study along with an investigation of the photoelectrical properties and application of PBBA7-C16 as a potential hole-transporting material for perovskite solar cells were performed.
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Polycyclic Arene Synthesis by Annulative π-Extension
Hideto Ito, Yasutomo Segawa, Kei Murakami et al. · Journal of the American Chemical Society · 2018 · 227 citations