Cyclotriveratrylene is a macrocycle

Macrocycle

A macrocycle is, as defined by IUPAC, "a cyclic macromolecule or a macromolecular cyclic portion of a molecule." In the chemical literature, organic chemists may consider any molecule containing a ring of nine or more atoms to be a macrocycle...

 and used in host-guest chemistry

Host-guest chemistry

In supramolecular chemistry, host-guest chemistry describes complexes that are composed of two or more molecules or ions that are held together in unique structural relationships by forces other than those of full covalent bonds. Host-guest chemistry encompasses the idea of molecular recognition...

 as a molecular host . The compound can be synthesised from veratrole alcohol

Veratrole alcohol

Veratrole alcohol, is an organic compound related to veratrole and also to benzyl alcohol. It can be obtained by reduction of Veratraldehyde . Veratrole alcohol is the raw material for the synthesis of cyclotriveratrylene, of some relevance to host-guest chemistry....

 by addition of a suitable acid which can be perchloric acid

Perchloric acid

Perchloric acid is the inorganic compound with the formula HClO4. Usually encountered as an aqueous solution, this colourless compound is a strong acid comparable in strength to sulfuric and nitric acids. It is a powerful oxidizer, but its aqueous solutions up to appr. 70% are remarkably inert,...

 in methanol or formic acid

Formic acid

Formic acid is the simplest carboxylic acid. Its chemical formula is HCOOH or HCO2H. It is an important intermediate in chemical synthesis and occurs naturally, most notably in the venom of bee and ant stings. In fact, its name comes from the Latin word for ant, formica, referring to its early...

 or sulfuric acid

Sulfuric acid

Sulfuric acid is a strong mineral acid with the molecular formula . Its historical name is oil of vitriol. Pure sulfuric acid is a highly corrosive, colorless, viscous liquid. The salts of sulfuric acid are called sulfates...

 in acetic acid

Acetic acid

Acetic acid is an organic compound with the chemical formula CH3CO2H . It is a colourless liquid that when undiluted is also called glacial acetic acid. Acetic acid is the main component of vinegar , and has a distinctive sour taste and pungent smell...

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An alternative is synthesis from veratrole and formaldehyde

Formaldehyde

Formaldehyde is an organic compound with the formula CH2O. It is the simplest aldehyde, hence its systematic name methanal.Formaldehyde is a colorless gas with a characteristic pungent odor. It is an important precursor to many other chemical compounds, especially for polymers...

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The ether

Ether

Ethers are a class of organic compounds that contain an ether group — an oxygen atom connected to two alkyl or aryl groups — of general formula R–O–R'. A typical example is the solvent and anesthetic diethyl ether, commonly referred to simply as "ether"...

 groups are situated at the upper rim. CTV has a bowl shaped conformation just like a crown ether

Crown ether

Crown ethers are cyclic chemical compounds that consist of a ring containing several ether groups. The most common crown ethers are oligomers of ethylene oxide, the repeating unit being ethyleneoxy, i.e., -CH2CH2O-. Important members of this series are the tetramer , the pentamer , and the hexamer...

. The compound is related to calixarene

Calixarene

A calixarene is a macrocycle or cyclic oligomer based on a hydroxyalkylation product of a phenol and an aldehyde. The word calixarene is derived from calix or chalice because this type of molecule resembles a vase and from the word arene that refers to the aromatic building block...

s.

CTV derivates are known to bind fullerene

Fullerene

A fullerene is any molecule composed entirely of carbon, in the form of a hollow sphere, ellipsoid, or tube. Spherical fullerenes are also called buckyballs, and they resemble the balls used in association football. Cylindrical ones are called carbon nanotubes or buckytubes...

s and the use of CTV's in the separation of mixtures of fullerenes has been demonstrated. They have also been used in the solubilizing and immobilizing of fullerene compounds. CTV derivatives are also known to form liquid crystal

Liquid crystal

Liquid crystals are a state of matter that have properties between those of a conventional liquid and those of a solid crystal. For instance, an LC may flow like a liquid, but its molecules may be oriented in a crystal-like way. There are many different types of LC phases, which can be...

s and they are used as structural units for polymer networks (gels) and polymers. With suitable metal complexes CTV's can form metallo-supramolecular oligomers or polymers.

When two CTV units are connected though molecular spacer

Molecular spacer

A Molecular spacer or simply a spacer in chemistry is any flexible part of a molecule providing a connection betweentwo other parts of a molecule....

s a molecular box is formed called a cryptophane

Cryptophane

Cryptophanes are a class of organic supramolecular compounds studied and synthesized primarily for molecular encapsulation and recognition. One possible noteworthy application of cryptophanes is encapsulation and storage of hydrogen gas for potential use in fuel cell automobiles...

. Cryptophanes are of interest in molecular encapsulation

Molecular encapsulation

Molecular encapsulation in supramolecular chemistry is the confinement of a guest molecule inside the cavity of a supramolecular host molecule...

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History

CTV was first synthesised by Gertrude Robinson (the first wife of Sir Robert Robinson) in 1915 but misdiagnosed as the dimer. In 1965 Lindsey identified the correct structure and coined cyclotriveratrylene as the name for the compound .