Naphthalenetetracarboxylic dianhydride

NTDA is most commonly used as a precursor to naphthalenediimides (NDIs) (such as napthalenetetracarboxylic diimide), a family of compounds with many uses.

The unsaturated tetrachloride hydrolyzes to enols that tautomerize to the bis-dione, which in turn can be oxidized to the tetracarboxylic acid.

[2] Symmetrical naphthalene diimides are synthesized by the condensation reaction of primary amines and the dianhydride.

These diimides are members of a broader class of compounds called rylenes, oligomers of naphthalene with bonds between the 1 and 1' and 8 and 8' positions.

NDIs are used in supramolecular chemistry due to their tendency to form charge-transfer complexes with crown ethers, e.g. to give rotaxanes and catenanes.

NTDA
Synthesis of NTDA
Synthesis of NTDA
Structure of NTDA. Distances in angstroms: O1 – C4, 1.182; O2 – C4, 1.375; O2 – C5, 1.365; O3 – C5, 1.189; C4 – C6, 1.494; C5 – C7, 1.494. [ 3 ]
Synthesis of symmetric and unsymmetric NDIs