Naphthalenetetracarboxylic diimide (NTCDI) is a solid

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

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 Crystal, crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 Parts-per notation ...

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 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 at –1.10 V vs. Fc/Fc⁺ in

Dichloromethane Dichloromethane (DCM, methylene chloride, or methylene bichloride) is an organochlorine compound with the formula . This colorless, volatile liquid with a chloroform-like, sweet odor is widely used as a solvent. Although it is not miscible with ...

. Its ability to accept electrons reflects the presence of an extended conjugated ring system and the

electron withdrawing group The electron (, or in nuclear reactions) is a subatomic particle with a negative one elementary electric charge. It is a fundamental particle that comprises the ordinary matter that makes up the universe, along with up and down quarks. E ...

s (carbonyl centers). NDI is used in

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

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., . Impor ...

s, e.g., to give

rotaxanes 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 trapped since ...

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 follo ...

into

DNA Deoxyribonucleic acid (; DNA) is a polymer composed of two polynucleotide chains that coil around each other to form a double helix. The polymer carries genetic instructions for the development, functioning, growth and reproduction of al ...

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

References

{{reflist Naphthalenes Imides Isoquinolinoisoquinolines