Naphthalenetetracarboxylic diimide (NTCDI) is a solid
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon- hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. Th ...
and one of the simplest naphthalenediimides (NDIs). NTCDI is produced from the parent
naphthalene via an intermediate compound
naphthalenetetracarboxylic dianhydride
Naphthalenetetracarboxylic dianhydride (NTDA) is an organic compound related to naphthalene. The compound is a beige solid. NTDA is most commonly used as a precursor to naphthalenediimides (NDIs) (such as napthalenetetracarboxylic diimide), a fam ...
.
Properties
NTCDI is redox-active, forming stable
radical anions near -1.10 V vs.
Fc/Fc+. Its ability to accept electrons reflects the presence of an extended
conjugated ring system and the
electron withdrawing groups (carbonyl centers). NDI is used in
supramolecular chemistry owing to its tendency to form
charge-transfer complexes with
crown ether
In organic chemistry, crown ethers are cyclic chemical compounds that consist of a ring containing several ether groups (). The most common crown ethers are cyclic oligomers of ethylene oxide, the repeating unit being ethyleneoxy, i.e., . I ...
s, e.g., to give
rotaxanes and
catenanes. As another consequence of their planar structure and electron-acceptor properties, NDIs
intercalate into
DNA. It is also suitable for fabrication of soft electronic devices.
References
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Naphthalenes