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Cryptophane

Class of organic compounds

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Source updated July 9, 2026

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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 can also serve as containers in which organic chemists can carry out reactions that would otherwise be difficult to run under normal conditions. Due to their unique molecular recognition properties, cryptophanes also hold great promise as a potentially new way to study the binding of organic molecules with substrates, particularly as pertaining to biological and biochemical applications.

01Discovery

Cryptophanes were discovered by André Collet and Jacqueline Gabard in 1981 when these researchers created, using template-directed synthesis, the first cryptophane, now known as cryptophane-A.

02Structure

Cryptophane cages are formed by two cup-shaped [1.1.1], orthocyclophane units (see cyclotriveratrylene), connected by three bridges (denoted Y). There are also choices of the peripheral substitutes R1 and R2 attached to the aromatic rings of the units. Most cryptophanes exhibit two diastereomeric forms (syn and anti), distinguished by their symmetry type. This general scheme offers a variety of choices (Y, R1, R2, and symmetry type) by which the shape, volume and chemical properties of the generally hydrophobic pocket inside the cage can be modified, making cryptophanes suitable for encapsulating many types of small molecules and even chemical reactions.

03General classification

Depending on their structure, cryptophane cages are classified according to the following table.

**Classification of known cryptophane structures**
Structure			Name
Bridges Y	R1	R2	anti	syn	described in
3 × O(CX₂)₂O, where X is H or D	OCX₃	OCX₃	A		Brotin et al.
3 × O(CX₂)₂O	OCH₂CO₂H	OCH₂CO₂H	A3
3 × O(CX₂)₂O	OCH₃	H	C	D
3 × O(CH₂)₃O	OCH₃	OCH₃	E	F
3 × O(CH₂)₃O	OCH₂CO₂H	OCH₂CO₂H	E3
3 × O(CH₂)₅O	OCH₃	OCH₃	O	P
3 × O(CH₂)₅O	OCH₂CO₂H	OCH₂CO₂H	O3
3 × OCH₂C≡CC≡CH₂O	CH₃	CH₃	γ (gamma)	δ (delta)
2 × O(CH₂)₂O, 1 × O(CH₂)₃O	OCH₃	OCH₃	223
2 × O(CH₂)₃O, 1 × O(CH₂)₂O	OCH₃	OCH₃	233
2 × O(CH₂)₂O, 1 × O(CH₂)₄O	OCH₃	OCH₃	224

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Sources and credits

This article is adapted from the Wikipedia article “Cryptophane”, written by its contributors and licensed under CC BY-SA 4.0. Fathomly has changed the layout, removed citation markers, navigation and maintenance notices, and adjusted punctuation. This adapted version is shared under the same license. For references, see the original article.

Images, from Wikimedia Commons:

Cryptophane general structure.gif by Xenonice, Public domain

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