Naphthalenetetracarboxylic diimide

is a solid organic compound and one of the simplest naphthalenediimides (NDIs).

NTCDI is produced from the parent naphthalene via an intermediate compound naphthalenetetracarboxylic dianhydride.

NTCDI is redox-active, forming stable radical anions at –1.10 V vs. Fc/Fc+ in Dichloromethane.

NDI is used in supramolecular chemistry owing to its tendency to form charge-transfer complexes with crown ethers, e.g., to give rotaxanes and catenanes.

As another consequence of their planar structure and electron-acceptor properties, NDIs intercalate into DNA.

Synthesis of symmetric and unsymmetric NDIs.