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A pyrogallolarene (also calix yrogallolarene) is a
Pyrogallol rene is simply made by mixing a solvent-free dispersion of
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.
...
, or a cyclic
Cycle, cycles, or cyclic may refer to:
Anthropology and social sciences
* Cyclic history, a theory of history
* Cyclical theory, a theory of American political history associated with Arthur Schlesinger, Sr.
* Social cycle, various cycles in s ...
oligomer, based on the condensation of pyrogallol
Pyrogallol is an organic compound with the formula C6H3(OH)3. It is a water-soluble, white solid although samples are typically brownish because of its sensitivity toward oxygen. It is one of three isomers of benzenetriols.
Production and reac ...
(1,2,3-trihydroxybenzene) and an aldehyde
In organic chemistry, an aldehyde () is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl grou ...
. Pyrogallolarenes are a type of 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 ...
, and a subset of resorcinarenes that are substituted with a hydroxyl
In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydro ...
at the 2-position.
Pyrogallolarenes, like all resorcinarenes, form inclusion complexes with other molecules forming a host–guest complex. Pyrogallolarenes (like resorcinarenes) self-assemble into larger supramolecular structures forming a hydrogen-bonded hexamer. The pyrogallolarene hexamer is unique from those formed from resorcinarene, in that it does not incorporate solvent molecules into the structure. Both in the crystalline state and in organic solvent
A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for ...
s, six molecules will form an assembly with an internal volume of around one cubic nanometer (nanocapsules) and shapes similar to the Archimedean solids. A number of solvent or other molecules may reside in the capsule interior. The pyrogallolarene hexamer is generally more stable than the resorcinarene hexamer, even in polar solvents.
Synthesis
The pyrogallolarene macrocycle is typically prepared by condensation ofpyrogallol
Pyrogallol is an organic compound with the formula C6H3(OH)3. It is a water-soluble, white solid although samples are typically brownish because of its sensitivity toward oxygen. It is one of three isomers of benzenetriols.
Production and reac ...
and an aldehyde
In organic chemistry, an aldehyde () is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl grou ...
in concentrated acid solution in the presence of an alcohol solvent, usually methanol or ethanol
Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an alcohol with the chemical formula . Its formula can be also written as or (an ethyl group linked to a ...
. The reaction conditions can usually be carefully adjusted to precipitate the pure product or the product may be purified by recrystallization.
Pyrogallol rene is simply made by mixing a solvent-free dispersion of isovaleraldehyde
Isovaleraldehyde organic compound, also known as 3-methylbutanal, with the formula (CH3)2CHCH2CHO. It is an aldehyde, a colorless liquid at STP, and found in low concentrations in many types of food. It can be produced commercially and is used as ...
with pyrogallol, and a catalytic amount of ''p''-toluenesulfonic acid, in a mortar and pestle
Mortar and pestle is a set of two simple tools used from the Stone Age to the present day to prepare ingredients or substances by crushing and grinding them into a fine paste or powder in the kitchen, laboratory, and pharmacy. The ''mortar'' ( ...
.{{cite journal , vauthors=Antesberger J, Cave GW, Ferrarelli MC, Heaven MW, Raston CL, Atwood JL , title=Solvent-free, direct synthesis of supramolecular nano-capsules , journal=Chemical Communications , volume=. , issue=7 , year=2005 , pages=892–894 , pmid=15700072 , doi=10.1039/b412251h
References