Supramolecular chemistry

Short description: Branch of chemistry

Supramolecular chemistry is the branch of chemistry concerning chemical systems composed of a discrete numbers of molecules. The strength of the forces responsible for spatial organization of the system ranges from weak intermolecular forces, electrostatic charge, or hydrogen bonding to strong covalent bonding, provided that the electronic coupling strength remains small relative to the energy parameters of the component.[1][2] 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 and electrostatic effects.[4][5] Important concepts advanced by supramolecular chemistry include molecular self-assembly, molecular folding, molecular recognition, host–guest chemistry, mechanically-interlocked molecular architectures, and dynamic covalent chemistry.[6] The study of non-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.

* Self-assembly of a circular double helicate[7]

* Host–guest complex within another host (cucurbituril)[8]

* Mechanically-interlocked molecules (rotaxane)[9]

* An example of a host–guest chemistry[10]

* Host–guest complex with a p-xylylenediammonium bound within a cucurbituril[11]

* Intramolecular self-assembly of a foldamer[12]

* Two pyrene butyric acids bound within a C-hexylpyrogallol[4]arenes nanocapsule. The side chains of the pyrene butyric acids are omitted.[13]

* Structure of two isophthalic acids bound to a host molecule through hydrogen bonds[14]

* Structure of a short peptide L-Lys-D-Ala-D-Ala (bacterial cell wall precursor) bound to the antibiotic vancomycin[15]

## Contents

* 1 History
* 2 Concepts
* 2.1 Molecular self-assembly
* 2.2 Molecular recognition and complexation
* 2.3 Template-directed synthesis
* 2.4 Mechanically interlocked molecular architectures
* 2.5 Dynamic covalent chemistry
* 2.6 Biomimetics
* 2.7 Imprinting
* 2.8 Molecular machinery
* 3 Building blocks
* 3.1 Synthetic recognition motifs
* 3.2 Macrocycles
* 3.3 Structural units
* 3.4 Photo-chemically and electro-chemically active units
* 3.5 Biologically-derived units
* 4 Applications
* 4.1 Materials technology
* 4.2 Catalysis
* 4.3 Medicine
* 4.4 Data storage and processing
* 5 See also
* 6 Reading
* 7 References
* 8 External links

## History

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

The existence of intermolecular forces was first postulated by Johannes Diderik van der Waals in 1873. However, Nobel laureate Hermann Emil Fischer developed supramolecular chemistry's philosophical roots. In 1894,[16] Fischer suggested that enzyme–substrate interactions take the form of a "lock and key", the fundamental principles of molecular 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 by Latimer and Rodebush in 1920.

With the deeper understanding of the non-covalent interactions, for example, the clear elucidation of DNA 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, and Jean-Pierre Sauvage were awarded the Nobel Prize in Chemistry, "for the design and synthesis of molecular machines".[19]

Carboxylic acid dimers

The term supermolecule (or supramolecule) was introduced by Karl Lothar Wolf et al. (Übermoleküle) in 1937 to describe hydrogen-bonded acetic acid dimers.[20][21] The term supermolecule is also used in biochemistry to describe complexes of biomolecules, such as peptides and oligonucleotides composed of multiple strands.[22]

Eventually, chemists applied these concepts to synthetic systems. One breakthrough came in the 1960s with the synthesis of the crown ethers by Charles J. Pedersen. Following this work, other researchers such as Donald J. Cram, Jean-Marie Lehn and Fritz 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 1987 Nobel 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

A ribosome is a biological machine that uses protein dynamics on nanoscales.

### Molecular self-assembly

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 a supramolecular assembly), and intramolecular self-assembly (or folding as demonstrated by foldamers and polypeptides). Molecular self-assembly also allows the construction of larger structures such as micelles, membranes, vesicles, liquid crystals, and is important to crystal engineering.[24]

### Molecular recognition and complexation

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 of molecular sensors and catalysis.[25][26][27][28]

### Template-directed synthesis

### Mechanically interlocked molecular architectures

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 include catenanes, rotaxanes, molecular knots, molecular Borromean rings,[29] 2D [c2]daisy chain polymer[30] and ravels.[31]

### Dynamic covalent chemistry

In dynamic 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

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

### Imprinting

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 only steric interactions, but more complex systems also incorporate hydrogen bonding and other interactions to improve binding strength and specificity.[34]

### Molecular machinery

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 and nanotechnology, and prototypes have been demonstrated using supramolecular concepts.[35] Jean-Pierre Sauvage, Sir J. Fraser Stoddart and Bernard L. Feringa shared the 2016 Nobel Prize in Chemistry for the 'design and synthesis of molecular machines'.[36]

## Building blocks

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

* The pi-pi charge-transfer interactions of bipyridinium with dioxyarenes or diaminoarenes have been used extensively for the construction of mechanically interlocked systems and in crystal engineering.
* The use of crown ether binding with metal or ammonium cations is ubiquitous in supramolecular chemistry.
* The formation of carboxylic acid dimers and other simple hydrogen bonding interactions.
* The complexation of bipyridines or terpyridines with ruthenium, silver or other metal ions is of great utility in the construction of complex architectures of many individual molecules.
* The complexation of porphyrins or phthalocyanines around metal ions gives access to catalytic, photochemical and electrochemical properties in addition to the complexation itself. These units are used a great deal by nature.

### Macrocycles

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 complex cyclophanes, and cryptands 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 bearing functional groups that connect the pieces via "self-assembly."[38]
* Metallacrowns are metallomacrocycles generated via a similar self-assembly approach from fused chelate-rings.

### Structural units

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 include polyether chains, biphenyls and terphenyls, and simple alkyl chains. The chemistry for creating and connecting these units is very well understood.
* nanoparticles, nanorods, fullerenes and dendrimers 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 with electrodes. Regular surfaces can be used for the construction of self-assembled monolayers and multilayers.
* 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

* Porphyrins, and phthalocyanines have highly tunable photochemical and electrochemical activity as well as the potential to form complexes.
* Photochromic and photoisomerizable groups can change their shapes and properties, including binding properties, upon exposure to light.
* Tetrathiafulvalene (TTF) and quinones have multiple stable oxidation states, and therefore can be used in redox reactions and electrochemistry.
* Other units, such as benzidine derivatives, viologens, and fullerenes, are useful in supramolecular electrochemical devices.

### Biologically-derived units

* The extremely strong complexation between avidin and biotin is instrumental in blood clotting, and has been used as the recognition motif to construct synthetic systems.
* The binding of enzymes with their cofactors 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

### Materials technology

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 using bottom-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 of metallogels, one-dimensional nanostructured materials formed from low molecular weight gelators and metal ions.[43] Many smart materials[44] are based on molecular recognition.[45]

### Catalysis

Main article: Chemistry:Supramolecular catalysis

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

### Medicine

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 of drug 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 disrupt protein–protein interactions that are important to cellular function.[50]

### Data storage and processing

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 supramolecular signal transduction devices. Data storage has been accomplished by the use of molecular switches with photochromic and photoisomerizable units, by electrochromic and redox-switchable units, and even by molecular motion. Synthetic molecular logic gates have been demonstrated on a conceptual level. Even full-scale computations have been achieved by semi-synthetic DNA computers.

## See also

* Organic chemistry
* Nanotechnology

## Reading

* Cook, T. R.; Zheng, Y.; Stang, P. J. (2013). "Metal-organic frameworks and self-assembled supramolecular coordination complexes: Comparing and contrasting the design, synthesis, and functionality of metal-organic materials". Chem. Rev. 113 (1): 734–77. doi:10.1021/cr3002824. PMID 23121121.
* Desiraju, G. R. (2013). "Crystal engineering: From molecule to crystal". J. Am. Chem. Soc. 135 (27): 9952–67. doi:10.1021/ja403264c. PMID 23750552. Bibcode: 2013JAChS.135.9952D.
* Seto, C. T.; Whitesides, G. M. (1993). "Molecular self-assembly through hydrogen bonding: Supramolecular aggregates based on the cyanuric acid-melamine lattice". J. Am. Chem. Soc. 115 (3): 905–916. doi:10.1021/ja00056a014. Bibcode: 1993JAChS.115..905S.

## References

1. ↑ Lehn, J. (1993). "Supramolecular Chemistry". Science 260 (5115): 1762–23. doi:10.1126/science.8511582. PMID 8511582. Bibcode: 1993Sci...260.1762L.
2. ↑ Lehn, J. (1995). Supramolecular Chemistry. Wiley-VCH. ISBN 978-3-527-29311-7.
3. ↑ Schneider, H. (2009). "Binding Mechanisms in Supramolecular Complexes". Angew. Chem. Int. Ed. Engl. 48 (22): 3924–77. doi:10.1002/anie.200802947. PMID 19415701.
4. ↑ Biedermann, F.; Schneider, H.J. (2016). "Experimental Binding Energies in Supramolecular Complexes". Chem. Rev. 116 (9): 5216–5300. doi:10.1021/acs.chemrev.5b00583. PMID 27136957.
5. ↑ Steed, Jonathan W.; Atwood, Jerry L. (2009). Supramolecular Chemistry (2nd ed.). Wiley. doi:10.1002/9780470740880. ISBN 978-0-470-51234-0.
6. ↑ Oshovsky, G. V.; Reinhoudt, D. N.; Verboom, W. (2007). "Supramolecular Chemistry in Water". Angewandte Chemie International Edition 46 (14): 2366–93. doi:10.1002/anie.200602815. PMID 17370285. https://ris.utwente.nl/ws/files/6610143/Oshovsky07supra.pdf.
7. ↑ Hasenknopf, B.; Lehn, J. M.; Kneisel, B. O.; Baum, G.; Fenske, D. (1996). "Self-Assembly of a Circular Double Helicate". Angewandte Chemie International Edition in English 35 (16): 1838–1840. doi:10.1002/anie.199618381.
8. ↑ Day, A. I.; Blanch, R. J.; Arnold, A. P.; Lorenzo, S.; Lewis, G. R.; Dance, I. (2002). "A Cucurbituril-Based Gyroscane: A New Supramolecular Form". Angewandte Chemie International Edition 41 (2): 275–7. doi:10.1002/1521-3773(20020118)41:2<275::AID-ANIE275>3.0.CO;2-M. PMID 12491407.
9. ↑ Bravo, J. A.; Raymo, F. I. M.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. (1998). "High Yielding Template-Directed Syntheses of [2]Rotaxanes". European Journal of Organic Chemistry 1998 (11): 2565–2571. doi:10.1002/(SICI)1099-0690(199811)1998:11<2565::AID-EJOC2565>3.0.CO;2-8.
10. ↑ Anderson, S.; Anderson, H. L.; Bashall, A.; McPartlin, M.; Sanders, J. K. M. (1995). "Assembly and Crystal Structure of a Photoactive Array of Five Porphyrins". Angewandte Chemie International Edition in English 34 (10): 1096–1099. doi:10.1002/anie.199510961.
11. ↑ Freeman, W. A. (1984). "Structures of the p-xylylenediammonium chloride and calcium hydrogensulfate adducts of the cavitand 'cucurbituril', C36H36N24O12". Acta Crystallographica Section B 40 (4): 382–387. doi:10.1107/S0108768184002354. Bibcode: 1984AcCrB..40..382F.
12. ↑ Schmitt, J. L.; Stadler, A. M.; Kyritsakas, N.; Lehn, J. M. (2003). "Helicity-Encoded Molecular Strands: Efficient Access by the Hydrazone Route and Structural Features". Helvetica Chimica Acta 86 (5): 1598–1624. doi:10.1002/hlca.200390137.
13. ↑ Dalgarno, S. J.; Tucker, S. A.; Bassil, D. B.; Atwood, J. L. (2005). "Fluorescent Guest Molecules Report Ordered Inner Phase of Host Capsules in Solution". Science 309 (5743): 2037–9. doi:10.1126/science.1116579. PMID 16179474. Bibcode: 2005Sci...309.2037D.
14. ↑ "A modular approach to constructing multi-site receptors for isophthalic acid". Chemical Communications (12): 1313–4. 1998. doi:10.1039/a707262g.
15. ↑ "Different modes of vancomycin and D-alanyl-D-alanine peptidase binding to cell wall peptide and a possible role for the vancomycin resistance protein". Antimicrobial Agents and Chemotherapy 34 (7): 1342–1347. July 1990. doi:10.1128/AAC.34.7.1342. PMID 2386365.
16. ↑ Fischer, E. (1894). "Einfluss der Configuration auf die Wirkung der Enzyme". Berichte der Deutschen Chemischen Gesellschaft 27 (3): 2985–2993. doi:10.1002/cber.18940270364. https://zenodo.org/record/1425780.
17. ↑ "Supramolecular chemistry" (in en), Wikipedia, 2023-01-25, https://en.wikipedia.org/w/index.php?title=Supramolecular_chemistry&oldid=1135615476, retrieved 2023-02-15
18. ↑ "The Nobel Prize in Chemistry 1987" (in en-US). https://www.nobelprize.org/prizes/chemistry/1987/summary/.
19. ↑ "The Nobel Prize in Chemistry 2016" (in en-US). https://www.nobelprize.org/prizes/chemistry/2016/summary/.
20. ↑ Wolf, Κ. L.; Frahm, H.; Harms, H. (1937-01-01). "Über den Ordnungszustand der Moleküle in Flüssigkeiten" (in de). Zeitschrift für Physikalische Chemie (Walter de Gruyter GmbH) 36B (1): 237-287. doi:10.1515/zpch-1937-3618. ISSN 2196-7156.
21. ↑ Historical Remarks on Supramolecular Chemistry – PDF (16 pg. paper)
22. ↑ Lehninger, Albert L. (1966). "Supramolecular organization of enzyme and membrane systems". Die Naturwissenschaften (Springer Science and Business Media LLC) 53 (3): 57–63. doi:10.1007/bf00594748. ISSN 0028-1042. PMID 5983868. Bibcode: 1966NW.....53...57L.
23. ↑ Schmeck, Harold M. Jr. (October 15, 1987) "Chemistry and Physics Nobels Hail Discoveries on Life and Superconductors; Three Share Prize for Synthesis of Vital Enzymes". New York Times
24. ↑ Ariga, K.; Hill, J. P.; Lee, M. V.; Vinu, A.; Charvet, R.; Acharya, S. (2008). "Challenges and breakthroughs in recent research on self-assembly". Science and Technology of Advanced Materials 9 (1). doi:10.1088/1468-6996/9/1/014109. PMID 27877935. Bibcode: 2008STAdM...9a4109A.
25. ↑ Kurth, D. G. (2008). "Metallo-supramolecular modules as a paradigm for materials science". Science and Technology of Advanced Materials 9 (1). doi:10.1088/1468-6996/9/1/014103. PMID 27877929. Bibcode: 2008STAdM...9a4103G.
26. ↑ Daze, K. (2012). "Supramolecular hosts that recognize methyllysines and disrupt the interaction between a modified histone tail and its epigenetic reader protein". Chemical Science 3 (9): 2695. doi:10.1039/C2SC20583A.
27. ↑ Bureekaew, S.; Shimomura, S.; Kitagawa, S. (2008). "Chemistry and application of flexible porous coordination polymers". Science and Technology of Advanced Materials 9 (1). doi:10.1088/1468-6996/9/1/014108. PMID 27877934. Bibcode: 2008STAdM...9a4108B.
28. ↑ Lehn, J. M. (1990). "Perspectives in Supramolecular Chemistry—From Molecular Recognition towards Molecular Information Processing and Self-Organization". Angewandte Chemie International Edition in English 29 (11): 1304–1319. doi:10.1002/anie.199013041.
29. ↑ Ikeda, T.; Stoddart, J. F. (2008). "Electrochromic materials using mechanically interlocked molecules". Science and Technology of Advanced Materials 9 (1). doi:10.1088/1468-6996/9/1/014104. PMID 27877930. Bibcode: 2008STAdM...9a4104I.
30. ↑ Tang, Z.-B.; Bian, L.; Miao, X.; Gao, H.; Liu, L.; Jiang, Q.; Sheng, D.; Xu, L. et al. (2025). "Synthesis of a crystalline two-dimensional [c2]daisy chain honeycomb network". Nature Synthesis 4. doi:10.1038/s44160-025-00791-x.
31. ↑ Li, F.; Clegg, J. K.; Lindoy, L. F.; MacQuart, R. B.; Meehan, G. V. (2011). "Metallosupramolecular self-assembly of a universal 3-ravel". Nature Communications 2. doi:10.1038/ncomms1208. PMID 21343923. Bibcode: 2011NatCo...2..205L.
32. ↑ Rowan, S. J.; Cantrill, S. J.; Cousins, G. R. L.; Sanders, J. K. M.; Stoddart, J. F. (2002). "Dynamic Covalent Chemistry". Angewandte Chemie International Edition 41 (6): 898–952. doi:10.1002/1521-3773(20020315)41:6<898::AID-ANIE898>3.0.CO;2-E. PMID 12491278.
33. ↑ Zhang, S. (2003). "Fabrication of novel biomaterials through molecular self-assembly". Nature Biotechnology 21 (10): 1171–8. doi:10.1038/nbt874. PMID 14520402.
34. ↑ Dickert, F. (1999). "Molecular imprinting in chemical sensing". TrAC Trends in Analytical Chemistry 18 (3): 192–199. doi:10.1016/S0165-9936(98)00123-X.
35. ↑ Balzani, V.; Gómez-López, M.; Stoddart, J. F. (1998). "Molecular Machines". Accounts of Chemical Research 31 (7): 405–414. doi:10.1021/ar970340y.
36. ↑ "The Nobel Prize in Chemistry 2016". Nobel Media AB 2014. https://www.nobelprize.org/nobel_prizes/chemistry/laureates/2016/.
37. ↑ Functional Metallosupramolecular Materials, Editors: John George Hardy, Felix H Schacher, Royal Society of Chemistry, Cambridge 2015, https://pubs.rsc.org/en/content/ebook/978-1-78262-267-3
38. ↑ Lee, S. J.; Lin, W. (2008). "Chiral Metallocycles: Rational Synthesis and Novel Applications". Accounts of Chemical Research 41 (4): 521–37. doi:10.1021/ar700216n. PMID 18271561.
39. ↑ Atwood, J. L.; Gokel, George W.; Barbour, Leonard J. (2017-06-22). Comprehensive Supramolecular Chemistry II. Amsterdam, Netherlands. p. 46. ISBN 978-0-12-803199-5. OCLC 992802408.
40. ↑ Chopra, Deepak, Royal Society of Chemistry (2019) (in English). Understanding intermolecular interactions in the solid state: approaches and techniques. London; Cambridge: Royal Society of Chemistry. ISBN 978-1-78801-079-5. OCLC 1103809341.
41. ↑ Schneider, H.-J. ( Ed.) (2012) Applications of Supramolecular Chemistry, CRC Press Taylor & Francis Boca Raton etc, [1]
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. doi:10.1016/j.ccr.2023.215225. ISSN 0010-8545. https://www.sciencedirect.com/science/article/pii/S001085452300214X.
44. ↑ Smart Materials Book Series, Royal Soc. Chem. Cambridge UK . http://pubs.rsc.org/bookshop/collections/series?issn=2046-0066
45. ↑ Chemoresponsive Materials /Stimulation by Chemical and Biological Signals, Schneider, H.-J. ; Ed:, (2015) The Royal Society of Chemistry, Cambridge https://dx.doi.org/10.1039/9781782622420
46. ↑ Meeuwissen, J.; Reek, J. N. H. (2010). "Supramolecular catalysis beyond enzyme mimics". Nat. Chem. 2 (8): 615–21. doi:10.1038/nchem.744. PMID 20651721. Bibcode: 2010NatCh...2..615M.
47. ↑ Webber, Matthew J.; Appel, Eric A.; Meijer, E. W.; Langer, Robert (18 December 2015). "Supramolecular biomaterials". Nature Materials 15 (1): 13–26. doi:10.1038/nmat4474. PMID 26681596. Bibcode: 2016NatMa..15...13W.
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.. The Alkali Metal Ions: Their Role in Life. Metal Ions in Life Sciences. 16. Springer. pp. 485–556. doi:10.1007/978-3-319-21756-7_14. ISBN 978-3-319-21755-0.
49. ↑ Smart Materials for Drug Delivery: Complete Set (2013) Royal Soc. Chem. Cambridge UK http://pubs.rsc.org/en/content/ebook/9781849735520
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". Journal of Controlled Release 155 (2): 200–10. doi:10.1016/j.jconrel.2011.04.027. PMID 21571017. https://hal.archives-ouvertes.fr/hal-02512499/file/1-s2.0-S0168365911002422-main.pdf.

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