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Cyclotriveratrylene (CTV) is an organic compound with the formula 6H2(OCH3)2CH2sub>3. It is a white solid that is soluble in organic solvents. The compound is a macrocycle and used in host–guest chemistry as a molecular host.
Operating via the same intermediates, an alternative synthesis involves the acid-catalyzed reaction of veratrole and formaldehyde. The method is similar to the reactions that give phenol formaldehyde resins except that the degree of polymerization is moderated by the methoxy substituents.
Synthesis
The compound can be synthesised fromveratrole 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.
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Operating via the same intermediates, an alternative synthesis involves the acid-catalyzed reaction of veratrole and formaldehyde. The method is similar to the reactions that give phenol formaldehyde resins except that the degree of polymerization is moderated by the methoxy substituents.
Host–guest behavior
CTV has a bowl shaped conformation, giving the molecule C3 symmetry. The ether groups are situated at the upper rim, but in contrast a crown ether typically do not interact with guests. The compound is related to calixarenes in terms of its host–guest properties and its synthesis CTV derivates are known to bind fullerenes 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 formliquid 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 spacer
A molecule is a group of two or more atoms held together by attractive forces known as chemical bonds; depending on context, the term may or may not include ions which satisfy this criterion. In quantum physics, organic chemistry, and bioche ...
s 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 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. AtwoodReferences
{{Reflist Macrocycles Catechol ethers Cyclophanes Nine-membered rings Methoxy compounds Tetracyclic compounds