Functionalized Corannulene Carbocations: A Structural Overview

摘要: A detailed structural overview of a family bowl-shaped polycyclic aromatic carbocations the type [C20H10R]+ with different R functionalities tethered to interior surface corannulene (C20H10) is provided. Changing identity surface-bound groups through alkyl chains spanning from one four carbon atoms and incorporating degree halogenation has led fine tuning bowl structures properties. The deformation core upon functionalization been revealed based on X-ray crystallographic analysis compared for series cations R=CH3, CH2Cl, CHCl2, CCl3, CH2CH3, CH2CH2Cl, CH2CH2Br. resulting have isolated several metal-based counterions, varying in size coordinating abilities ([AlCl4]−, [AlBr4]−, [(SnCl)(GaCl4)2]−, [Al(OC(CF3)3)4]−). variety aggregation patterns solid state intermolecular interactions ranging cation–anion π–π stacking halogen⋅⋅⋅π interactions. For [C20H10CH2Cl]+ ion crystallized conformation group attached central five-membered ring moiety was found depend solid-state environment defined by anions. Solution NMR UV/Vis investigations used complement diffraction studies this corannulene-based demonstrate their association solvent molecules.