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Supramolecular chemistry

From Wikipedia, the free encyclopedia
Branch of chemistry

Supramolecular chemistry is the branch ofchemistry concerningchemical systems composed ofdiscrete numbers ofmolecules. The strength of the forces responsible for spatial organization of the system ranges from weakintermolecular forces,electrostatic charge, orhydrogen bonding to strongcovalent bonding, provided that the electronic coupling strength remains small relative to the energy parameters of the component.[1][2][page needed] While traditional chemistry concentrates on the covalent bond, supramolecular chemistry examines the weaker and reversible non-covalent interactions between molecules.[3] These forces include hydrogen bonding,metal coordination,hydrophobic forces,van der Waals forces,pi–pi interactions andelectrostatic effects.[4][5]

Important concepts advanced by supramolecular chemistry includemolecular self-assembly,molecular folding,molecular recognition,host–guest chemistry,mechanically-interlocked molecular architectures, anddynamic covalent chemistry.[6] The study ofnon-covalent interactions is crucial to understanding many biological processes that rely on these forces for structure and function.Biological systems are often the inspiration for supramolecular research.

History

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18-crown-6 can be synthesized from using potassium ion as the template cation

The existence of intermolecular forces was first postulated byJohannes Diderik van der Waals in 1873. However, Nobel laureateHermann Emil Fischer developed supramolecular chemistry's philosophical roots. In 1894,[16] Fischer suggested thatenzyme–substrate interactions take the form of a "lock and key", the fundamental principles ofmolecular recognition and host–guest chemistry. In the early twentieth century non-covalent bonds were understood in gradually more detail, with the hydrogen bond being described byLatimer and Rodebush in 1920.

With the deeper understanding of the non-covalent interactions, for example, the clear elucidation ofDNA structure, chemists started to emphasize the importance of non-covalent interactions.[17] In 1967, Charles J. Pedersen discovered crown ethers, which are ring-like structures capable of chelating certain metal ions. Then, in 1969,Jean-Marie Lehn discovered a class of molecules similar to crown ethers, called cryptands. After that,Donald J. Cram synthesized many variations to crown ethers, on top of separate molecules capable of selective interaction with certain chemicals. The three scientists were awarded the Nobel Prize in Chemistry in 1987 for "development and use of molecules with structure-specific interactions of high selectivity".[18] In 2016,Bernard L. Feringa, Sir J.Fraser Stoddart, andJean-Pierre Sauvage were awarded the Nobel Prize in Chemistry, "for the design and synthesis ofmolecular machines".[19]

Carboxylic aciddimers

The termsupermolecule (orsupramolecule) was introduced byKarl Lothar Wolfet al. (Übermoleküle) in 1937 to describehydrogen-bondedacetic aciddimers.[20][21] The term supermolecule is also used inbiochemistry to describe complexes ofbiomolecules, such aspeptides andoligonucleotides composed of multiple strands.[22]

Eventually, chemists applied these concepts to synthetic systems. One breakthrough came in the 1960s with the synthesis of thecrown ethers byCharles J. Pedersen. Following this work, other researchers such asDonald J. Cram,Jean-Marie Lehn andFritz Vögtle reported a variety of three-dimensional receptors, and throughout the 1980s research in the area gathered a rapid pace with concepts such as mechanically interlocked molecular architectures emerging.

The influence of supramolecular chemistry was established by the 1987Nobel Prize for Chemistry which was awarded to Donald J. Cram, Jean-Marie Lehn, and Charles J. Pedersen in recognition of their work in this area.[23] The development of selective "host–guest" complexes in particular, in which a host molecule recognizes and selectively binds a certain guest, was cited as an important contribution.

Concepts

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Aribosome is abiological machine that usesprotein dynamics onnanoscales.

Molecular self-assembly

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Molecular self-assembly is the construction of systems without guidance or management from an outside source (other than to provide a suitable environment). The molecules are directed to assemble through non-covalent interactions. Self-assembly may be subdivided into intermolecular self-assembly (to form asupramolecular assembly), and intramolecular self-assembly (orfolding as demonstrated byfoldamers and polypeptides). Molecular self-assembly also allows the construction of larger structures such asmicelles,membranes,vesicles,liquid crystals, and is important tocrystal engineering.[24]

Molecular recognition and complexation

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Molecular recognition is the specific binding of a guest molecule to a complementary host molecule to form a host–guest complex. Often, the definition of which species is the "host" and which is the "guest" is arbitrary. The molecules are able to identify each other using non-covalent interactions. Key applications of this field are the construction ofmolecular sensors andcatalysis.[25][26][27][28]

Template-directed synthesis

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Molecular recognition and self-assembly may be used with reactive species in order to pre-organize a system for a chemical reaction (to form one or more covalent bonds). It may be considered a special case of supramolecularcatalysis. Non-covalent bonds between the reactants and a "template" hold the reactive sites of the reactants close together, facilitating the desired chemistry. This technique is particularly useful for situations where the desired reaction conformation is thermodynamically or kinetically unlikely, such as in the preparation of large macrocycles. This pre-organization also serves purposes such as minimizing side reactions, lowering theactivation energy of the reaction, and producing desiredstereochemistry. After the reaction has taken place, the template may remain in place, be forcibly removed, or may be "automatically" decomplexed on account of the different recognition properties of the reaction product. The template may be as simple as a single metal ion or may be extremely complex.[citation needed]

Mechanically interlocked molecular architectures

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Mechanically interlocked molecular architectures consist of molecules that are linked only as a consequence of their topology. Some non-covalent interactions may exist between the different components (often those that were used in the construction of the system), but covalent bonds do not. Supramolecular chemistry, and template-directed synthesis in particular, is key to the efficient synthesis of the compounds. Examples of mechanically interlocked molecular architectures includecatenanes,rotaxanes,molecular knots,molecular Borromean rings,[29] 2D [c2]daisy chain polymer[30] and ravels.[31]

Dynamic covalent chemistry

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Indynamic covalent chemistry covalent bonds are broken and formed in a reversible reaction under thermodynamic control. While covalent bonds are key to the process, the system is directed by non-covalent forces to form the lowest energy structures.[32]

Biomimetics

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Many synthetic supramolecular systems are designed to copy functions of biological systems. Thesebiomimetic architectures can be used to learn about both the biological model and the synthetic implementation. Examples include photoelectrochemical systems, catalytic systems,protein design andself-replication.[33]

Imprinting

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Molecular imprinting describes a process by which a host is constructed from small molecules using a suitable molecular species as a template. After construction, the template is removed leaving only the host. The template for host construction may be subtly different from the guest that the finished host binds to. In its simplest form, imprinting uses onlysteric interactions, but more complex systems also incorporate hydrogen bonding and other interactions to improve binding strength and specificity.[34]

Molecular machinery

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Molecular machines are molecules or molecular assemblies that can perform functions such as linear or rotational movement, switching, and entrapment. These devices exist at the boundary between supramolecular chemistry andnanotechnology, and prototypes have been demonstrated using supramolecular concepts.[35]Jean-Pierre Sauvage,Sir J. Fraser Stoddart andBernard L. Feringa shared the 2016Nobel Prize in Chemistry for the 'design and synthesis of molecular machines'.[36]

Building blocks

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Supramolecular systems are rarely designed from first principles. Rather, chemists have a range of well-studied structural and functional building blocks that they are able to use to build up larger functional architectures. Many of these exist as whole families of similar units, from which the analog with the exact desired properties can be chosen.

Synthetic recognition motifs

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Macrocycles

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Macrocycles are very useful in supramolecular chemistry, as they provide whole cavities that can completely surround guest molecules and may be chemically modified to fine-tune their properties.

  • Cyclodextrins,calixarenes, cucurbiturils and crown ethers are readily synthesized in large quantities, and are therefore convenient for use in supramolecular systems.
  • More complexcyclophanes, andcryptands can be synthesised to provide more tailored recognition properties.
  • Supramolecular metallocycles are macrocyclic aggregates with metal ions in the ring, often formed from angular and linear modules.[37] Common metallocycle shapes in these types of applications include triangles, squares, and pentagons, each bearingfunctional groups that connect the pieces via "self-assembly."[38]
  • Metallacrowns are metallomacrocycles generated via a similarself-assembly approach from fusedchelate-rings.

Structural units

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Many supramolecular systems require their components to have suitable spacing and conformations relative to each other, and therefore easily employed structural units are required.[39]

  • Commonly used spacers and connecting groups includepolyether chains,biphenyls andterphenyls, and simplealkyl chains. The chemistry for creating and connecting these units is very well understood.
  • nanoparticles,nanorods,fullerenes anddendrimers offer nanometer-sized structure and encapsulation units.
  • Surfaces can be used as scaffolds for the construction of complex systems and also for interfacing electrochemical systems withelectrodes. Regular surfaces can be used for the construction ofself-assembled monolayers andmultilayers.
  • The understanding of intermolecular interactions in solids has undergone a major renaissance via inputs from different experimental and computational methods in the last decade. This includes high-pressure studies in solids and "in situ" crystallization of compounds which are liquids at room temperature along with the use of electron density analysis, crystal structure prediction and DFT calculations in solid state to enable a quantitative understanding of the nature, energetics and topological properties associated with such interactions in crystals.[40]

Photo-chemically and electro-chemically active units

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Biologically-derived units

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  • The extremely strong complexation betweenavidin andbiotin is instrumental inblood clotting, and has been used as the recognition motif to construct synthetic systems.
  • The binding ofenzymes with theircofactors has been used as a route to produce modified enzymes, electrically contacted enzymes, and even photoswitchable enzymes.
  • DNA has been used both as a structural and as a functional unit in synthetic supramolecular systems.

Applications

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Materials technology

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Supramolecular chemistry has found many applications,[41] in particular molecular self-assembly processes have been applied to the development of new materials. Large structures can be readily accessed usingbottom-up synthesis as they are composed of small molecules requiring fewer steps to synthesize. Thus most of the bottom-up approaches to nanotechnology are based on supramolecular chemistry.[42] This approach is applied in the synthesis ofmetallogels, one-dimensionalnanostructured materials formed from low molecular weight gelators and metal ions.[43] Manysmart materials[44] are based on molecular recognition.[45]

Catalysis

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Main article:Supramolecular catalysis

A major application of supramolecular chemistry is the design and understanding ofcatalysts and catalysis. Non-covalent interactions influence the binding reactants.[46]

Medicine

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Design based on supramolecular chemistry has led to numerous applications in the creation of functional biomaterials and therapeutics.[47] Supramolecular biomaterials afford a number of modular and generalizable platforms with tunable mechanical, chemical and biological properties. These include systems based on supramolecular assembly of peptides, host–guest macrocycles, high-affinity hydrogen bonding, and metal–ligand interactions.

A supramolecular approach has been used extensively to create artificial ion channels for the transport of sodium and potassium ions into and out of cells.[48]

Supramolecular chemistry is also important to the development of new pharmaceutical therapies by understanding the interactions at a drug binding site. The area ofdrug delivery has also made critical advances as a result of supramolecular chemistry providing encapsulation and targeted release mechanisms.[49] In addition, supramolecular systems have been designed to disruptprotein–protein interactions that are important to cellular function.[50]

Data storage and processing

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Supramolecular chemistry has been used to demonstrate computation functions on a molecular scale. In many cases, photonic or chemical signals have been used in these components, but electrical interfacing of these units has also been shown by supramolecularsignal transduction devices.Data storage has been accomplished by the use ofmolecular switches withphotochromic andphotoisomerizable units, byelectrochromic andredox-switchable units, and even by molecular motion. Syntheticmolecular logic gates have been demonstrated on a conceptual level. Even full-scale computations have been achieved by semi-syntheticDNA computers.

See also

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Reading

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References

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  30. ^Tang, Z.-B.; Bian, L.; Miao, X.; Gao, H.; Liu, L.; Jiang, Q.; Sheng, D.; Xu, L.; Sue, A. C.-H.; Zheng, X.; Liu, Z. C. (2025). "Synthesis of a crystalline two-dimensional [c2]daisy chain honeycomb network".Nature Synthesis.4:922–930.doi:10.1038/s44160-025-00791-x.
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  40. ^Chopra, Deepak, Royal Society of Chemistry (2019).Understanding intermolecular interactions in the solid state: approaches and techniques. London; Cambridge: Royal Society of Chemistry.ISBN 978-1-78801-079-5.OCLC 1103809341.{{cite book}}: CS1 maint: multiple names: authors list (link)
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  42. ^Gale, P.A. and Steed, J.W. (eds.) (2012)Supramolecular Chemistry: From Molecules to Nanomaterials. Wiley.ISBN 978-0-470-74640-0
  43. ^Picci, Giacomo; Caltagirone, Claudia; Garau, Alessandra; Lippolis, Vito; Milia, Jessica; Steed, Jonathan W. (2023-10-01)."Metal-based gels: Synthesis, properties, and applications".Coordination Chemistry Reviews.492 215225.doi:10.1016/j.ccr.2023.215225.ISSN 0010-8545.
  44. ^Smart Materials Book Series, Royal Soc. Chem. Cambridge UK .http://pubs.rsc.org/bookshop/collections/series?issn=2046-0066
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  46. ^Meeuwissen, J.; Reek, J. N. H. (2010). "Supramolecular catalysis beyond enzyme mimics".Nat. Chem.2 (8):615–21.Bibcode:2010NatCh...2..615M.doi:10.1038/nchem.744.PMID 20651721.{{cite journal}}: CS1 maint: multiple names: authors list (link)
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  48. ^Rodríguez-Vázquez, Nuria; Fuertes, Alberto; Amorín, Manuel; Granja, Juan R. (2016). "Chapter 14. Bioinspired Artificial Sodium and Potassium Ion Channels". In Sigel, Astrid; Sigel, Helmut; Sigel, Roland K.O. (eds.).The Alkali Metal Ions: Their Role in Life. Metal Ions in Life Sciences. Vol. 16. Springer. pp. 485–556.doi:10.1007/978-3-319-21756-7_14.ISBN 978-3-319-21755-0.PMID 26860310.
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  50. ^Bertrand, N.; Gauthier, M. A.; Bouvet, C. L.; Moreau, P.; Petitjean, A.; Leroux, J. C.; Leblond, J. (2011)."New pharmaceutical applications for macromolecular binders"(PDF).Journal of Controlled Release.155 (2):200–10.doi:10.1016/j.jconrel.2011.04.027.PMID 21571017.S2CID 41385952.

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