Cyclotriveratrylene (CTV) is an

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 ...

with the formula ₆H₂(OCH₃)₂CH₂sub>3. It is a white solid that is soluble in organic solvents. The compound is a

macrocycle Macrocycles are often described as molecules and ions containing a ring of twelve or more atoms. Classical examples include the crown ethers, calixarenes, porphyrins, and cyclodextrins. Macrocycles describe a large, mature area of chemistry. ...

and used in

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 che ...

as a molecular host.

Synthesis

The compound can be synthesised from

veratrole alcohol Veratrole alcohol (veratryl 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 which i ...

upon acid catalysis. : Cyclotriveratrylene synthesis

Operating via the same intermediates, an alternative synthesis involves the acid-catalyzed reaction of

veratrole 1,2-Dimethoxybenzene, commonly known as veratrole, is an organic compound with the formula CH(OCH). It is one of three isomers of dimethoxybenzene. It is a colorless liquid, with a pleasant odor and slight solubility in water. It is the dimethyl ...

and

formaldehyde Formaldehyde ( , ) (systematic name methanal) is a naturally occurring organic compound with the formula and structure . The pure compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde (refer to section F ...

. The method is similar to the reactions that give

phenol formaldehyde resin Phenol formaldehyde resins (PF) or phenolic resins (also infrequently called phenoplasts) are synthetic polymers obtained by the reaction of phenol or substituted phenol with formaldehyde. Used as the basis for Bakelite, PFs were the first commerc ...

s except that the

degree of polymerization The degree of polymerization, or DP, is the number of monomeric units in a macromolecule or polymer or oligomer molecule. For a homopolymer, there is only one type of monomeric unit and the ''number-average'' degree of polymerization is given by ...

is moderated by the methoxy substituents.

Host–guest behavior

CTV has a bowl shaped conformation, giving the molecule C₃ symmetry. The

ether In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula , where R and R′ represent the alkyl or aryl groups. Ethers can again be c ...

groups are situated at the upper rim, but in contrast a

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 ...

typically do not interact with guests. The compound is related to

calixarene A calixarene is a macrocycle or cyclic oligomer based on a methylene-linked phenols. With hydrophobic cavities that can hold smaller molecules or ions, calixarenes belong to the class of cavitands known in host–guest chemistry. Nomenclature Cal ...

s in terms of its host–guest properties and its synthesis CTV derivates are known to bind

fullerene A fullerene is an allotrope of carbon whose molecule consists of carbon atoms connected by single and double bonds so as to form a closed or partially closed mesh, with fused rings of five to seven atoms. The molecule may be a hollow sphere, ...

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 (LC) is a state of matter whose properties are between those of conventional liquids and those of solid crystals. For example, a liquid crystal may flow like a liquid, but its molecules may be oriented in a crystal-like way. T ...

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 spacers a molecular box is formed called a

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 po ...

. Cryptophanes are of interest in

molecular encapsulation In supramolecular chemistry, molecular encapsulation is the confinement of a guest molecule inside the cavity of a supramolecular host molecule (molecular capsule, molecular container or cage compounds). Examples of supramolecular host molecule ...

History

CTV was first synthesised by

Gertrude Robinson Gertrude Robinson (October 7, 1890 – March 19, 1962) was an American actress of the silent era. Biography She appeared in 164 films between 1908 and 1925. She was born in New York City and died in Hollywood, California. She was the fi ...

in 1915 but misdiagnosed as the dimer. In 1965, Lindsey identified the correct structure and coined cyclotriveratrylene as the name for the compound.''Supramolecular Chemistry'' Jonathan W. Steed, Jerry L. Atwood

References

{{Reflist Macrocycles Catechol ethers Cyclophanes Nine-membered rings Methoxy compounds Tetracyclic compounds