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. The ...

and one of the simplest naphthalenediimides (NDIs). NTCDI is produced from the parent

naphthalene Naphthalene is an organic compound with formula . It is the simplest polycyclic aromatic hydrocarbon, and is a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 ppm by mass. As an aromati ...

via an intermediate compound naphthalenetetracarboxylic dianhydride.

Properties

NTCDI is redox-active, forming stable

radical anion In organic chemistry, a radical anion is a free radical species that carries a negative charge. Radical anions are encountered in organic chemistry as reduced derivatives of polycyclic aromatic compounds, e.g. sodium naphthenide. An example of a ...

s 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 group In chemistry, an electron-withdrawing group (EWG) is a substituent that has some of the following kinetic and thermodynamic implications: *with regards to electron transfer, electron-withdrawing groups enhance the oxidizing power tendency of ...

s (carbonyl centers). NDI is used in

supramolecular chemistry Supramolecular chemistry refers to the branch of chemistry concerning chemical systems composed of a discrete number of molecules. The strength of the forces responsible for spatial organization of the system range from weak intermolecular forces, ...

owing to its tendency to form

charge-transfer complexes In chemistry, a charge-transfer (CT) complex or electron-donor-acceptor complex describes a type of supramolecular assembly of two or more molecules or ions. The assembly consists of two molecules that self-attract through electrostatic forces, ...

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., . Impo ...

s, e.g., to give

rotaxanes In chemistry, a rotaxane () is a mechanically interlocked molecular architecture consisting of a dumbbell-shaped molecule which is threaded through a macrocycle (see graphical representation). The two components of a rotaxane are kinetically t ...

and

catenane In macromolecular chemistry, a catenane () is a mechanically interlocked molecular architecture consisting of two or more interlocked macrocycles, i.e. a molecule containing two or more intertwined rings. The interlocked rings cannot be se ...

s. As another consequence of their planar structure and electron-acceptor properties, NDIs

intercalate Intercalation may refer to: *Intercalation (chemistry), insertion of a molecule (or ion) into layered solids such as graphite * Intercalation (timekeeping), insertion of a leap day, week or month into some calendar years to make the calendar foll ...

into DNA. It is also suitable for fabrication of soft electronic devices.

References

{{reflist Naphthalenes