Supramolecular chemistry

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Supramolecular chemistry refers to the branch of chemistry concerning chemical systems composed of a discrete number of molecules. The strength of the forces responsible for spatial organization of the system range 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] [ 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 and electrostatic effects. [4] [5]

Contents

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.

History

18-crown-6 can be synthesized from using potassium ion as the template cation 18-crown-6 was synthesized using potassium ion as the template cation.png
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, [14] 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. [15] 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”. [16] 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". [17]

Carboxylic acid dimers Carboxylic acid dimers.png
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. [18] [19] The term supermolecule is also used in biochemistry to describe complexes of biomolecules, such as peptides and oligonucleotides composed of multiple strands. [20]

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. [21] 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 Protein translation.gif
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. [22]

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. [23] [24] [25] [26]

Template-directed synthesis

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 supramolecular catalysis. 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 the activation energy of the reaction, and producing desired stereochemistry. 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

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 [27] and ravels. [28]

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. [29]

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. [30]

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. [31]

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. [32] 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'. [33]

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

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.

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. [36]

Photo-chemically and electro-chemically active units

Biologically-derived units

Applications

Materials technology

Supramolecular chemistry has found many applications, [38] 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. [39] Many smart materials [40] are based on molecular recognition. [41]

Catalysis

A major application of supramolecular chemistry is the design and understanding of catalysts and catalysis. Non-covalent interactions influence the binding reactants. [42]

Medicine

Design based on supramolecular chemistry has led to numerous applications in the creation of functional biomaterials and therapeutics. [43] 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. [44]

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. [45] In addition, supramolecular systems have been designed to disrupt protein–protein interactions that are important to cellular function. [46]

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

Reading


Related Research Articles

An intermolecular force is the force that mediates interaction between molecules, including the electromagnetic forces of attraction or repulsion which act between atoms and other types of neighbouring particles, e.g. atoms or ions. Intermolecular forces are weak relative to intramolecular forces – the forces which hold a molecule together. For example, the covalent bond, involving sharing electron pairs between atoms, is much stronger than the forces present between neighboring molecules. Both sets of forces are essential parts of force fields frequently used in molecular mechanics.

<span class="mw-page-title-main">Molecular recognition</span> Type of non-covalent bonding

The term molecular recognition refers to the specific interaction between two or more molecules through noncovalent bonding such as hydrogen bonding, metal coordination, hydrophobic forces, van der Waals forces, π-π interactions, halogen bonding, or resonant interaction effects. In addition to these direct interactions, solvents can play a dominant indirect role in driving molecular recognition in solution. The host and guest involved in molecular recognition exhibit molecular complementarity. Exceptions are molecular containers, including, e.g., nanotubes, in which portals essentially control selectivity. Selective partioning of molecules between two or more phases can also result in molecular recognition. In partitioning-based molecular recognition the kinetics and equilibrium conditions are governed by the presence of solutes in the two phases.

<span class="mw-page-title-main">Host–guest chemistry</span> Supramolecular structures held together other than by covalent bonds

In supramolecular chemistry, host–guest chemistry describes complexes that are composed of two or more molecules or ions that are held together in unique structural relationships by forces other than those of full covalent bonds. Host–guest chemistry encompasses the idea of molecular recognition and interactions through non-covalent bonding. Non-covalent bonding is critical in maintaining the 3D structure of large molecules, such as proteins and is involved in many biological processes in which large molecules bind specifically but transiently to one another.

<span class="mw-page-title-main">Cucurbituril</span> Ring molecule able to store other molecules within itself

In host-guest chemistry, cucurbiturils are macrocyclic molecules made of glycoluril monomers linked by methylene bridges. The oxygen atoms are located along the edges of the band and are tilted inwards, forming a partly enclosed cavity (cavitand). The name is derived from the resemblance of this molecule with a pumpkin of the family of Cucurbitaceae.

In chemistry, a non-covalent interaction differs from a covalent bond in that it does not involve the sharing of electrons, but rather involves more dispersed variations of electromagnetic interactions between molecules or within a molecule. The chemical energy released in the formation of non-covalent interactions is typically on the order of 1–5 kcal/mol. Non-covalent interactions can be classified into different categories, such as electrostatic, π-effects, van der Waals forces, and hydrophobic effects.

<span class="mw-page-title-main">Salt bridge (protein and supramolecular)</span> Combination of hydrogen and ionic bonding in chemistry

In chemistry, a salt bridge is a combination of two non-covalent interactions: hydrogen bonding and ionic bonding. Ion pairing is one of the most important noncovalent forces in chemistry, in biological systems, in different materials and in many applications such as ion pair chromatography. It is a most commonly observed contribution to the stability to the entropically unfavorable folded conformation of proteins. Although non-covalent interactions are known to be relatively weak interactions, small stabilizing interactions can add up to make an important contribution to the overall stability of a conformer. Not only are salt bridges found in proteins, but they can also be found in supramolecular chemistry. The thermodynamics of each are explored through experimental procedures to access the free energy contribution of the salt bridge to the overall free energy of the state.

In chemistry, mechanically interlocked molecular architectures (MIMAs) are molecules that are connected as a consequence of their topology. This connection of molecules is analogous to keys on a keychain loop. The keys are not directly connected to the keychain loop but they cannot be separated without breaking the loop. On the molecular level, the interlocked molecules cannot be separated without the breaking of the covalent bonds that comprise the conjoined molecules; this is referred to as a mechanical bond. Examples of mechanically interlocked molecular architectures include catenanes, rotaxanes, molecular knots, and molecular Borromean rings. Work in this area was recognized with the 2016 Nobel Prize in Chemistry to Bernard L. Feringa, Jean-Pierre Sauvage, and J. Fraser Stoddart.

Supramolecular polymers are a subset of polymers where the monomeric units are connected by reversible and highly directional secondary interactions–that is, non-covalent bonds. These non-covalent interactions include van der Waals interactions, hydrogen bonding, Coulomb or ionic interactions, π-π stacking, metal coordination, halogen bonding, chalcogen bonding, and host–guest interaction. Their behavior can be described by the theories of polymer physics) in dilute and concentrated solution, as well as in the bulk.

<span class="mw-page-title-main">Molecular sensor</span>

A molecular sensor or chemosensor is a molecular structure that is used for sensing of an analyte to produce a detectable change or a signal. The action of a chemosensor, relies on an interaction occurring at the molecular level, usually involves the continuous monitoring of the activity of a chemical species in a given matrix such as solution, air, blood, tissue, waste effluents, drinking water, etc. The application of chemosensors is referred to as chemosensing, which is a form of molecular recognition. All chemosensors are designed to contain a signalling moiety and a recognition moiety, that is connected either directly to each other or through a some kind of connector or a spacer. The signalling is often optically based electromagnetic radiation, giving rise to changes in either the ultraviolet and visible absorption or the emission properties of the sensors. Chemosensors may also be electrochemically based. Small molecule sensors are related to chemosensors. These are traditionally, however, considered as being structurally simple molecules and reflect the need to form chelating molecules for complexing ions in analytical chemistry. Chemosensors are synthetic analogues of biosensors, the difference being that biosensors incorporate biological receptors such as antibodies, aptamers or large biopolymers.

<span class="mw-page-title-main">Molecular self-assembly</span> Movement of molecules into a defined arrangement without outside influence

In chemistry and materials science, molecular self-assembly is the process by which molecules adopt a defined arrangement without guidance or management from an outside source. There are two types of self-assembly: intermolecular and intramolecular. Commonly, the term molecular self-assembly refers to the former, while the latter is more commonly called folding.

In chemistry, a halogen bond occurs when there is evidence of a net attractive interaction between an electrophilic region associated with a halogen atom in a molecular entity and a nucleophilic region in another, or the same, molecular entity. Like a hydrogen bond, the result is not a formal chemical bond, but rather a strong electrostatic attraction. Mathematically, the interaction can be decomposed in two terms: one describing an electrostatic, orbital-mixing charge-transfer and another describing electron-cloud dispersion. Halogen bonds find application in supramolecular chemistry; drug design and biochemistry; crystal engineering and liquid crystals; and organic catalysis.

<span class="mw-page-title-main">Dynamic combinatorial chemistry</span>

Dynamic combinatorial chemistry (DCC); also known as constitutional dynamic chemistry (CDC) is a method to the generation of new molecules formed by reversible reaction of simple building blocks under thermodynamic control. The library of these reversibly interconverting building blocks is called a dynamic combinatorial library (DCL). All constituents in a DCL are in equilibrium, and their distribution is determined by their thermodynamic stability within the DCL. The interconversion of these building blocks may involve covalent or non-covalent interactions. When a DCL is exposed to an external influence, the equilibrium shifts and those components that interact with the external influence are stabilised and amplified, allowing more of the active compound to be formed.

Coordination cages are three-dimensional ordered structures in solution that act as hosts in host–guest chemistry. They are self-assembled in solution from organometallic precursors, and often rely solely on noncovalent interactions rather than covalent bonds. Coordinate bonds are useful in such supramolecular self-assembly because of their versatile geometries. However, there is controversy over calling coordinate bonds noncovalent, as they are typically strong bonds and have covalent character. The combination of a coordination cage and a guest is a type of inclusion compound. Coordination complexes can be used as "nano-laboratories" for synthesis, and to isolate interesting intermediates. The inclusion complexes of a guest inside a coordination cage show intriguing chemistry as well; often, the properties of the cage will change depending on the guest. Coordination complexes are molecular moieties, so they are distinct from clathrates and metal-organic frameworks.

<span class="mw-page-title-main">Two-dimensional polymer</span>

A two-dimensional polymer (2DP) is a sheet-like monomolecular macromolecule consisting of laterally connected repeat units with end groups along all edges. This recent definition of 2DP is based on Hermann Staudinger's polymer concept from the 1920s. According to this, covalent long chain molecules ("Makromoleküle") do exist and are composed of a sequence of linearly connected repeat units and end groups at both termini.

<span class="mw-page-title-main">Supramolecular catalysis</span> Field of chemistry

Supramolecular catalysis refers to an application of supramolecular chemistry, especially molecular recognition and guest binding, toward catalysis. This field was originally inspired by enzymatic system which, unlike classical organic chemistry reactions, utilizes non-covalent interactions such as hydrogen bonding, cation-pi interaction, and hydrophobic forces to dramatically accelerate rate of reaction and/or allow highly selective reactions to occur. Because enzymes are structurally complex and difficult to modify, supramolecular catalysts offer a simpler model for studying factors involved in catalytic efficiency of the enzyme. Another goal that motivates this field is the development of efficient and practical catalysts that may or may not have an enzyme equivalent in nature.

Cyclobis(paraquat-<i>p</i>-phenylene) Chemical compound

Cyclobis(paraquat-p-phenylene) belongs to the class of cyclophanes, and consists of aromatic units connected by methylene bridges. It is able to incorporate small guest molecule and has played an important role in host–guest chemistry and supramolecular chemistry.

Latticial metal complex or grid complex is a supramolecular complex of several metal atoms and coordinating ligands which form a grid-like structural motif. The structure formation usually occurs while on thermodynamic molecular self-assembly. They have properties that make them interesting for information technology as the future storage materials. Chelate ligands are used as ligands in tetrahedral or octahedral structures, which mostly use nitrogen atoms in pyridine like ring systems other than donor centers. Suitable metal ions are in accordance with octahedral coordinating transition metal ions such as Mn or rare tetrahedral Coordinating such as Ag used.

Metallogels are one-dimensional nanostructured materials, which constitute a growing class in the Supramolecular chemistry field. Non-covalent interactions, such as hydrophobic interactions, π-π interactions, and hydrogen bonding, are among the responsible forces for the formation of those gels from small molecules. However, the main driving force for the formation of a metallogel is the metal-ligand coordination. Once the structure has been established, it resists gravitational force when inverted.

<span class="mw-page-title-main">Polyrotaxane</span>

Polyrotaxane is a type of mechanically interlocked molecule consisting of strings and rings, in which multiple rings are threaded onto a molecular axle and prevented from dethreading by two bulky end groups. As oligomeric or polymeric species of rotaxanes, polyrotaxanes are also capable of converting energy input to molecular movements because the ring motions can be controlled by external stimulus. Polyrotaxanes have attracted much attention for decades, because they can help build functional molecular machines with complicated molecular structure.

<span class="mw-page-title-main">Roeland Nolte</span> Dutch chemist (1944–2024)

Roeland J. M. Nolte was a Dutch chemist, known for his work in the fields of organic chemistry, biochemistry, polymer chemistry, and supramolecular chemistry. He was an emeritus Royal Netherlands Academy of Arts and Sciences professor and an emeritus professor of organic chemistry at Radboud University in Nijmegen, The Netherlands. Until his death, he held a special chair, i.e. professor of molecular nanotechnology, at Radboud University. Nolte was considered to be one of the pioneers of the field of supramolecular chemistry, which encompasses the design and synthesis of new chemical structures from low molecular weight compounds and biopolymers using non-covalent interactions. He published many studies on supramolecular assembly and biomimetic catalysts, which find applications in the field of nanomaterials and medicine.

References

  1. ↑ Lehn, J. (1993). "Supramolecular Chemistry". Science. 260 (5115): 1762–23. Bibcode:1993Sci...260.1762L. doi:10.1126/science.8511582. PMID   8511582.
  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" (PDF). Angewandte Chemie International Edition. 46 (14): 2366–93. doi:10.1002/anie.200602815. PMID   17370285.
  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.
  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. Bibcode:2005Sci...309.2037D. doi:10.1126/science.1116579. PMID   16179474. S2CID   41468421.
  14. ↑ 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.
  15. ↑ "Supramolecular chemistry", Wikipedia, 2023-01-25, retrieved 2023-02-15
  16. ↑ "The Nobel Prize in Chemistry 1987". NobelPrize.org. Retrieved 2023-02-15.
  17. ↑ "The Nobel Prize in Chemistry 2016". NobelPrize.org. Retrieved 2023-02-15.
  18. ↑ Wolf, Κ. L.; Frahm, H.; Harms, H. (1937-01-01). "Über den Ordnungszustand der Moleküle in Flüssigkeiten" [The State of Arrangement of Molecules in Liquids]. Zeitschrift für Physikalische Chemie (in German). 36B (1). Walter de Gruyter GmbH: 237-287. doi:10.1515/zpch-1937-3618. ISSN   2196-7156.
  19. ↑ Historical Remarks on Supramolecular Chemistry – PDF (16 pg. paper)
  20. ↑ Lehninger, Albert L. (1966). "Supramolecular organization of enzyme and membrane systems". Die Naturwissenschaften. 53 (3). Springer Science and Business Media LLC: 57–63. doi:10.1007/bf00594748. ISSN   0028-1042.
  21. ↑ 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
  22. ↑ 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): 014109. Bibcode:2008STAdM...9a4109A. doi:10.1088/1468-6996/9/1/014109. PMC   5099804 . PMID   27877935. Open Access logo PLoS transparent.svg
  23. ↑ Kurth, D. G. (2008). "Metallo-supramolecular modules as a paradigm for materials science". Science and Technology of Advanced Materials. 9 (1): 014103. Bibcode:2008STAdM...9a4103G. doi:10.1088/1468-6996/9/1/014103. PMC   5099798 . PMID   27877929. Open Access logo PLoS transparent.svg
  24. ↑ 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.
  25. ↑ Bureekaew, S.; Shimomura, S.; Kitagawa, S. (2008). "Chemistry and application of flexible porous coordination polymers". Science and Technology of Advanced Materials. 9 (1): 014108. Bibcode:2008STAdM...9a4108B. doi:10.1088/1468-6996/9/1/014108. PMC   5099803 . PMID   27877934. Open Access logo PLoS transparent.svg
  26. ↑ 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.
  27. ↑ Ikeda, T.; Stoddart, J. F. (2008). "Electrochromic materials using mechanically interlocked molecules". Science and Technology of Advanced Materials. 9 (1): 014104. Bibcode:2008STAdM...9a4104I. doi:10.1088/1468-6996/9/1/014104. PMC   5099799 . PMID   27877930. Open Access logo PLoS transparent.svg
  28. ↑ 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: 205. Bibcode:2011NatCo...2..205L. doi: 10.1038/ncomms1208 . PMID   21343923.
  29. ↑ 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.
  30. ↑ Zhang, S. (2003). "Fabrication of novel biomaterials through molecular self-assembly". Nature Biotechnology. 21 (10): 1171–8. doi:10.1038/nbt874. PMID   14520402. S2CID   54485012.
  31. ↑ 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.
  32. ↑ Balzani, V.; Gómez-López, M.; Stoddart, J. F. (1998). "Molecular Machines". Accounts of Chemical Research. 31 (7): 405–414. doi:10.1021/ar970340y.
  33. ↑ "The Nobel Prize in Chemistry 2016". Nobelprize.org. Nobel Media AB 2014. Retrieved 14 January 2017.
  34. ↑ 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
  35. ↑ 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.
  36. ↑ Atwood, J. L.; Gokel, George W.; Barbour, Leonard J. (2017-06-22). Comprehensive Supramolecular Chemistry II. Amsterdam, Netherlands. p. 46. ISBN   9780128031995. OCLC   992802408.{{cite book}}: CS1 maint: location missing publisher (link)
  37. ↑ 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)
  38. ↑ Schneider, H.-J. ( Ed.) (2012) Applications of Supramolecular Chemistry, CRC Press Taylor & Francis Boca Raton etc,
  39. ↑ Gale, P.A. and Steed, J.W. (eds.) (2012) Supramolecular Chemistry: From Molecules to Nanomaterials. Wiley. ISBN   978-0-470-74640-0
  40. ↑ Smart Materials Book Series, Royal Soc. Chem. Cambridge UK . http://pubs.rsc.org/bookshop/collections/series?issn=2046-0066
  41. ↑ 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
  42. ↑ 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)
  43. ↑ Webber, Matthew J.; Appel, Eric A.; Meijer, E. W.; Langer, Robert (18 December 2015). "Supramolecular biomaterials". Nature Materials. 15 (1): 13–26. Bibcode:2016NatMa..15...13W. doi:10.1038/nmat4474. PMID   26681596.
  44. ↑ 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. PMID   26860310.
  45. ↑ Smart Materials for Drug Delivery: Complete Set (2013) Royal Soc. Chem. Cambridge UK http://pubs.rsc.org/en/content/ebook/9781849735520
  46. ↑ 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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