Kinetic versus Thermodynamic Control Over Multiple Conformations of Di‐2,7‐naphthihexaphyrin(1.1.1.1.1.1)
Bartosz Szyszko, Paweł Rymut, Maksym Matviyishyn, Agata Białońska, Lechosław Latos‐Grażyński
Abstract
Di-2,7-naphthihexaphyrin(1.1.1.1.1.1), a non-aromatic carba-analogue of the hexaphyrin(1.1.1.1.1.1), incorporating two built-in 2,7-naphthylene moieties was synthesized as two separate, conformationally locked stereoisomers. Both conformers followed complex protonation pathways involving structurally different species, which can be targeted under kinetic and thermodynamic control. The neutralization of the ultimate dicationic product, accessible from both stereoisomers of the free base, allowed to realize the complex conformational switching cycle involving six structurally different species.
Topics & Concepts
Conformational isomerismProtonationChemistryKinetic controlStereochemistryKinetic energyMoleculeOrganic chemistryCatalysisPhysicsIonQuantum mechanicsPorphyrin and Phthalocyanine ChemistryPhotosynthetic Processes and MechanismsMetal-Catalyzed Oxygenation Mechanisms