acridanbased

Acridanbased is a term used in organic chemistry to describe compounds that incorporate the acridan scaffold, a nitrogen-containing polycyclic framework related to acridine. The family centers on 9,10-dihydroacridine (acridan) and its derivatives, including N-substituted acridans and the oxidized acridanium salts. The label acridanbased encompasses a broad range of structural variations built on this core.

Structural and property features in acridanbased compounds arise from the rigid, tricyclic ring system and the presence of a tertiary amine at the core. Substitutions at the peri and other positions, as well as N-substitutions, tune redox potentials, photophysical properties, and solubility. The ability to oxidize acridan to a cationic acridinium form is a defining feature, offering facile access to powerful oxidants used in catalysis and materials science.

Applications of acridanbased compounds are diverse. In organocatalysis and photoredox chemistry, acridan-based cations serve as strong single-electron-oxidants under visible light, enabling a range of oxidation, dehydrogenation, and cross-coupling reactions. They are also explored in organic electronics, including light-emitting devices and dye chemistry, as well as in sensor and polymerization contexts where tunable fluorescence and redox properties are advantageous.

Synthesis and handling typically involve constructing the acridan core through cyclization or annulation strategies, followed by N-functionalization and subsequent oxidation to acridinium salts where needed. Acridanbased materials can be sensitive to air and light, particularly in their charged forms, necessitating careful, sometimes inert, handling.

see also acridinium, acridine, photoredox catalysis.