Host–guest chemistry

Short description: Supramolecular structures held together other than by covalent bonds

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In supramolecular chemistry,[1] 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.

Although non-covalent interactions could be roughly divided into those with more electrostatic or dispersive contributions, there are few commonly mentioned types of non-covalent interactions: ionic bonding, hydrogen bonding, van der Waals forces and hydrophobic interactions.[2]

Host–guest interaction has raised significant attention since it was discovered. Many biological processes and material designs require the host–guest interaction. There are several typical host molecules, such as, cyclodextrin, crown ether, et al..

Crystal structure of a host–guest complex with a p-xylylenediammonium bound within a cucurbituril [3] A guest N2 is bound within a host hydrogen-bonded capsule [4]

"Host molecules" usually have a "pore-like" structure that is able to capture a "guest molecule." Although called molecules, hosts and guests are often ions. The driving forces of the interaction vary, such as hydrophobic effect and van der Waals forces.[5][6][7][8]

Binding between host and guest can be highly selective, in which case the interaction is called molecular recognition. Often, a dynamic equilibrium exists between the unbound and the bound states:

H+G⇌ HG
H ="host", G ="guest", HG ="host–guest complex"

The "host" component is often the larger molecule, and it encloses the smaller, "guest" molecule. In biological systems, the terms of host and guest are commonly referred to as enzyme and substrate respectively.[9]

## Contents

* 1 Inclusion and clathrate compounds
* 2 Molecular encapsulation
* 3 Macrocyclic hosts
* 3.1 Calixarenes
* 3.2 Cyclodextrins and cucurbiturils
* 3.3 Cryptophanes
* 3.4 Crown ethers and cryptands
* 3.5 Chiral capsules
* 4 Polymeric hosts
* 5 Thermodynamics of host–guest interactions
* 5.1 Experimental techniques
* 6 Aspiration applications
* 6.1 Self-healing
* 6.2 Encapsulation and release: fragrances and drugs
* 6.3 Encryption
* 6.4 Mechanical properties
* 6.5 Sensing
* 6.6 Conformational switching
* 6.7 Environmental applications
* 6.8 Alcohol
* 7 See also
* 8 Further reading
* 9 References

## Inclusion and clathrate compounds

Cd(CN)2·CCl4: Cadmium cyanide clathrate framework (in blue) containing carbon tetrachloride (C atoms in gray and disordered Cl positions in green)

Closely related to host–guest chemistry are inclusion compounds (also known as an inclusion complexes). Here, a chemical complex in which one chemical compound (the "host") has a cavity into which a "guest" compound can be accommodated. The interaction between the host and guest involves van der Waals bonding. The definition of inclusion compounds is very broad, extending to channels formed between molecules in a crystal lattice in which guest molecules can fit.

IUPAC definition

The IUPAC Gold Book defines an inclusion compound as a complex in which a host forms a cavity or lattice of channels that accommodates a guest species; the association is non-covalent and generally driven by van der Waals forces.[10]

Another related class of compounds are clathrates, which often consist of a lattice that traps or contains molecules.[11] The word clathrate is derived from the Latin clathratus (clatratus), meaning 'with bars, latticed'.[12]

## Molecular encapsulation

Molecular encapsulation concerns the confinement of a guest within a larger host. In some cases, true host–guest reversibility is observed. In other cases, the encapsulated guest cannot escape.[13]

Molecular encapsulation of a nitrobenzene bound within a hemicarcerand[14]

An important implication of encapsulation (and host–guest chemistry in general) is that the guest behaves differently than when in solution. Guest molecules that would react by bimolecular pathways are often stabilized because they cannot combine with other reactants. Compounds, like cyclobutadiene,[15] arynes or cycloheptatetraene, that are normally highly unstable in solution have been isolated at room temperature when molecularly encapsulated.[16][17] Large metalla-assemblies, known as metallaprisms, contain a conformationally flexible cavity that allows them to host a variety of guest molecules. These assemblies have shown promise as agents of drug delivery to cancer cells.

Encapsulation can control reactivity. For instance, excited state reactivity of free 1-phenyl-3-tolyl-2-proponanone (abbreviated A-CO-B) yields products A-A, B-B, and AB, which result from decarbonylation followed by random recombination of radicals A• and B•. Whereas, the same substrate upon encapsulation reacts to yield the controlled recombination product A-B, and rearranged products (isomers of A-CO-B).[18]

## Macrocyclic hosts

Organic hosts are occasionally called cavitands. The original definition proposed by Cram includes many classes of molecules: cyclodextrins, calixarenes, pillararenes and cucurbiturils.[19]

### Calixarenes

Calixarenes and related formaldehyde-arene condensates (resorcinarenes and pyrogallolarenes) form a class of hosts that form inclusion compounds.[5][20] Pillararenes (pillered arenes) are a related family of formaldehyde-derived oligomeric rings. One famous illustration of the stabilizing effect of host–guest complexation is the stabilization of cyclobutadiene by such an organic host.[21]

### Cyclodextrins and cucurbiturils

Chemical structure of pillar[5]arene

Cyclodextrins (CDs) are tubular molecules composed of several glucose units connected by ether bonds. The three kinds of CDs--α-CD (six units), β-CD (seven units), and γ-CD (eight units)--differ in their cavity sizes: 5, 6, and 8 Å, respectively. α-CD can thread onto one PEG chain, while γ-CD can thread onto two PEG chains. β-CD can bind with thiophene-based molecules.[5] Cyclodextrins are well established hosts for the formation of inclusion compounds.[1][2][3] An example is when ferrocene is inserted into the cyclodextrin at 100°C under hydrothermal conditions.[22]

Cucurbiturils are macrocyclic molecules made of glycoluril (=C

2=) monomers, linked by methylene bridges (–CH
2–). The oxygen atoms are located along the edges of the band and are tilted inwards, forming a partly enclosed cavity (cavitand). Cucurbit[n]urils have similar size of γ-CD, which also behave similarly (e.g., one cucurbit[n]uril can thread onto two PEG chains).[5]

### Cryptophanes

a) Structure of Cryptophanes. b) Structure of Resorcinarenes and Pyrogallolarenes. c) Structure of cucurbit[n]urils. Redrawn from source material.[5]

The structure of cryptophanes contain six phenyl rings, mainly connected in four ways. Due to the phenyl groups and aliphatic chains, the cages inside cryptophanes are highly hydrophobic, suggesting the capability of capturing non-polar molecules. Based on this, cryptophanes can be employed to capture xenon in aqueous solution to help biological studies.[5]

### Crown ethers and cryptands

a) Structure of 18-crown-6. b) Threading of crown ether and 1,2,3-triazole (rotaxane). Redrawn from source material. c) Inclusion of a-CD and polyethylene glycol (PEG) d) Threading of b-cyclodextrin and thiophene-based molecule. Redrawn from source material.[5]

Crown ethers bind cations. Small crown ethers, e.g. 12-crown-4, bind well to small ions such as Li+. Large crowns, such as 24-crown-8, bind better to larger ions.[5] Crown ethers also bind to some neutral molecules, e.g., 1, 2, 3- triazole. Crown ethers can also be threaded with slender linear molecules and/or polymers, creating supramolecular structures called rotaxanes. Given that the crown ethers are not bound to the chains, they can move up and down the threading molecule.[8] Crown ether complexes of metal cations (and the corresponding complexes of cryptands) are not considered to be inclusion complexes, since the guest is bound by forces stronger than van der Waals bonding.

### Chiral capsules

The "egg shell" molecular capsuleFigure 7. Interlacing salt bridges that connect the two halves of the molecular capsule

Molecular capsules have been developed with a chiral interiors.[23] This capsule is made of two halves, like a plastic easter egg (Figure 6). Salt bridge interactions between the two halves cause them to self-assemble in solution (Figure 7). They are stable even when heated to 60 °C.

## Polymeric hosts

Zeolites have open framework structures with cavities where guest species can reside. Zeolites are rigid due to Aluminosilicates being their composition. Many structures are known, some of which are used as catalysts and for separations.[11]

Silica clathrasil are compounds that are structurally similar to clathrate hydrates with a SiO2 framework and can be found in a range of marine sediments.[24]

Clathrate compounds, with formula A8B16X30, where A is an alkaline earth metal, B is a group III element, and X is an element from group IV, have been explored for thermoelectric devices. Thermoelectric materials follow a design strategy called the phonon glass electron crystal concept.[25][26] Low thermal conductivity and high electrical conductivity is desired to produce the Seebeck Effect. When the guest and host framework are appropriately tuned, clathrates can exhibit low thermal conductivity, i.e., phonon glass behavior, while electrical conductivity through the host framework is undisturbed, allowing clathrates to exhibit electron crystal.

Hofmann clathrates are coordination polymers, with the formula Ni(CN)4·Ni(NH3)2(arene). These materials crystallize with small aromatic guests (benzene, certain xylenes), and this selectivity has been commercially exploited for the separation of these hydrocarbons.[11] Metal organic frameworks (MOFs) form clathrates.

Urea, a small molecule with the formula O=C(NH

2, has the property of crystallizing in open but rigid networks. The cost of efficient molecular packing is compensated by hydrogen-bonding. Ribbons of hydrogen-bonded urea molecules form a tunnel-like host into which many organic guests bind. Urea-clathrates have been well investigated for separations.[27] Several other organic molecules form clathrates: thiourea, hydroquinone, and Dianin's compound.[11]

## Thermodynamics of host–guest interactions

Main article: Chemistry:Determination of equilibrium constants

When the host and guest molecules combine to form a single complex, the equilibrium is represented as

H+G⇋HG

and the equilibrium constant, K, is defined as

K=[HG][H][G]

where [X] denotes the concentration of a chemical species X (all activity coefficients are assumed to have a numerical values of 1). The mass-balance equations, at any data point,

TH=[H]+K[H][G]
TG=[G]+K[H][G]

where TG and TH represent the total concentrations, of host and guest, can be reduced to a single quadratic equation in, say, [G] and so can be solved analytically for any given value of K. The concentrations [H] and [HG] can then derived.

[H]=TH−TG+[G]
[HG]=K[H][G]

The next step in the calculation is to calculate the value, Xicalc, of a quantity corresponding to the quantity observed Xiobs. Then, a sum of squares, U, over all data points, np, can be defined as

U=∑i=1,np(Xiobs−Xicalc)2

and this can be minimized with respect to the stability constant value, K, and a parameter such as the chemical shift of the species HG (nmr data) or its molar absorbency (uv/vis data). This procedure is applicable to 1:1 adducts.

### Experimental techniques

Set of NMR spectra from a host–guest titration Typical ultraviolet–visible spectra for a host–guest system

With nuclear magnetic resonance (NMR) spectra, the observed chemical shift value, δ, arising from a given atom contained in a reagent molecule and one or more complexes of that reagent, will be the concentration-weighted average of all shifts of those chemical species. Chemical exchange is assumed to be rapid on the NMR time-scale.

Using UV-vis spectroscopy, the absorbance of each species is proportional to the concentration of that species, according to the Beer–Lambert law.

Aλ=ℓ∑i=1Nεi,λci

Where λ is a wavelength, ℓ is the optical path length of the cuvette which contains the solution of the N compounds (chromophores), εi,λ is the molar absorbance (also known as the extinction coefficient) of the ith chemical species at the wavelength λ, and ci is its concentration. When the concentrations have been calculated and absorbance has been measured for samples with various concentrations of host and guest, the Beer–Lambert law provides a set of equations, at a given wavelength, that can be solved by a linear least-squares process for the unknown extinction coefficient values at that wavelength.

Host–guest structures can be probed by their luminescence. A rigid matrix protects emitters from being quenched, extending the lifetime of phosphorescence.[28] In this circumstance, α-CD and CB can be used,[29][30] in which the phosphor serves as a guest to interact with the host. For example, when 4-phenylpyridium derivatives interacted with CB, and copolymerized with acrylamide, the resulting polymer yielded ~2 s of phosphorescence lifetime. Additionally, Zhu et al. used crown ether and potassium ions to modify the polymer and enhance the emission of phosphorescence.[31]

Another technique for evaluating host–guest interactions is calorimetry.

## Aspiration applications

Host guest complexation is pervasive in biochemistry. Many protein hosts recognize and hence selectively bind other biomolecules. When the protein host is an enzyme, the guests are called substrates.

### Self-healing

Self-healing mechanism of host–guest interaction by a) using host–small-guest molecule and b) host–polymer. Redrawn from source material.[32][33]

A self-healing hydrogel can be constructed from modified cyclodextrin and adamantane.[32][34] Another strategy is to use the interaction between the polymer backbone and host molecule (host molecule threading onto the polymer). If the threading process is fast enough, self-healing can also be achieved.[33]

### Encapsulation and release: fragrances and drugs

Cyclodextrin forms inclusion compounds with fragrances which are more stable towards exposure to light and air. When incorporated into textiles, the fragrance lasts much longer due to the slow-release action.[35]

Photolytically sensitive caged compounds have been examined as containers for releasing drugs or reagents.[36][37]

### Encryption

An encryption system constructed by pillar[5]arene, spiropyran and pentanenitrile (free state and grafted to polymer) was created by Wang et al.. After UV irradiation, spiropyran transforms into merocyanine. When visible light was shined on the material, the merocyanine close to the pillar[5]arene-free pentanenitrile complex had faster transformation to spiropyran; on the contrary, the one close to pillar[5]arene-grafted pentanenitrile complex has much slower transformation rate. This spiropyran–merocyanine transformation can be used for message encryption.[38] Another strategy is based on the metallacages and polycyclic aromatic hydrocarbons.[39] Because of the fluorescence emission differences between the complex and the cages, the information could be encrypted.

### Mechanical properties

Although some host–guest interactions are not strong, increasing the amount of the host–guest interaction can improve the mechanical properties of the materials. As an example, threading the host molecules onto the polymer is one of the commonly used strategies for increasing the mechanical properties of the polymer. It takes time for the host molecules to de-thread from the polymer, which can be a way of energy dissipation.[34][40][41] Another method is to use the slow exchange host–guest interaction. Though the slow exchange improves the mechanical properties, simultaneously, self-healing properties will be sacrificed.[42]

### Sensing

Silicon surfaces functionalized with tetraphosphonate cavitands have been used to singularly detect sarcosine in water and urine solutions.[43]

Traditionally, chemical sensing has been approached with a system that contains a covalently bound indicator to a receptor though a linker. Once the analyte binds, the indicator changes color or fluoresces. This technique is called the indicator–spacer–receptor approach (ISR).[44] In contrast to ISR, indicator-displacement assay (IDA) utilizes a non-covalent interaction between a receptor (the host), indicator, and an analyte (the guest). Similar to ISR, IDA also utilizes colorimetric (C-IDA) and fluorescence (F-IDA) indicators. In an IDA assay, a receptor is incubated with the indicator. When the analyte is added to the mixture, the indicator is released to the environment. Once the indicator is released it either changes color (C-IDA) or fluoresces (F-IDA).[45]

Types of chemosensors: (1) indicator–spacer–receptor (ISR), (2) indicator-displacement assay (IDA)

IDA offers several advantages versus the traditional ISR chemical sensing approach. First, it does not require the indicator to be covalently bound to the receptor. Secondly, since there is no covalent bond, various indicators can be used with the same receptor. Lastly, the media in which the assay may be used is diverse.[46]

Indicator-displacement assay indicators: (1) azure A, (2) thiazole orange

Chemical sensing techniques such as C-IDA have biological implications. For example, protamine is a coagulant that is routinely administered after cardiopulmonary surgery that counter acts the anti-coagulant activity of herapin. In order to quantify the protamine in plasma samples, a colorimetric displacement assay is used. Azure A dye is blue when it is unbound, but when it is bound to herapin it shows a purple color. The binding between Azure A and heparin is weak and reversible. This allows protamine to displace Azure A. Once the dye is liberated it displays a purple color. The degree to which the dye is displaced is proportional to the amount of protamine in the plasma.[47]

F-IDA has been used by Kwalczykowski and co-workers to monitor the activities of helicase in E. coli. In this study they used thiazole orange as the indicator. The helicase unwinds the dsDNA to make ssDNA. The fluorescence intensity of thiazole orange has a greater affinity for dsDNA than ssDNA and its fluorescence intensity is higher when it is bound to dsDNA than when it is unbound.[48][49]

### Conformational switching

A crystalline solid has been traditionally viewed as a static entity where the movements of its atomic components are limited to its vibrational equilibrium. As seen by the transformation of graphite to diamond, solid to solid transformation can occur under physical or chemical pressure. It has been proposed that the transformation from one crystal arrangement to another occurs in a cooperative manner.[50][51] Most of these studies have been focused in studying an organic or metal-organic framework.[52][53] In addition to studies of macromolecular crystalline transformation, there are also studies of single-crystal molecules that can change their conformation in the presence of organic solvents. An organometallic complex has been shown to morph into various orientations depending on whether it is exposed to solvent vapors or not.[54]

### Environmental applications

Host guest systems have been proposed to remove hazardous materials. Certain calix[4]arenes bind cesium-137 ions, which could in principle be applied to clean up radioactive wastes. Some receptors bind carcinogens.[55][56]

### Alcohol

According to food chemist Udo Pollmer of the European Institute of Food and Nutrition Sciences in Munich, alcohol can be molecularly encapsulated in cyclodextrines, a sugar derivate. In this way, encapsuled in small capsules, the fluid can be handled as a powder. The cyclodextrines can absorb an estimated 60 percent of their own weight in alcohol.[57] A US patent has been registered for the process as early as 1974.[58]

## See also

* Cryptophane

## Further reading

* Dsouza, Roy N.; Pischel, Uwe; Nau, Werner M. (2011). "Fluorescent Dyes and Their Supramolecular Host/Guest Complexes with Macrocycles in Aqueous Solution". Chemical Reviews 111 (12): 7941–7980. doi:10.1021/cr200213s. PMID 21981343.
* Yu, Guocan; Jie, Kecheng; Huang, Feihe (2015). "Supramolecular Amphiphiles Based on Host–Guest Molecular Recognition Motifs". Chemical Reviews 115 (15): 7240–7303. doi:10.1021/cr5005315. PMID 25716119.
* Hu, Jingjing; Xu, Tongwen; Cheng, Yiyun (2012). "NMR Insights into Dendrimer-Based Host–Guest Systems". Chemical Reviews 112 (7): 3856–3891. doi:10.1021/cr200333h. PMID 22486250.
* Xia, Danyu; Wang, Pi; Ji, Xiaofan; Khashab, Niveen M.; Sessler, Jonathan L.; Huang, Feihe (2020). "Functional Supramolecular Polymeric Networks: The Marriage of Covalent Polymers and Macrocycle-Based Host–Guest Interactions". Chemical Reviews 120 (13): 6070–6123. doi:10.1021/acs.chemrev.9b00839. PMID 32426970.
* Qu, Da-Hui; Wang, Qiao-Chun; Zhang, Qi-Wei; Ma, Xiang; Tian, He (2015). "Photoresponsive Host–Guest Functional Systems". Chemical Reviews 115 (15): 7543–7588. doi:10.1021/cr5006342. PMID 25697681.

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3. ↑ Freeman, Wade A. (1984). "Structures of the p-xylylenediammonium chloride and calcium hydrogensulfate adducts of the cavitand 'cucurbituril', C36H36N24O12". Acta Crystallographica B 40 (4): 382–387. doi:10.1107/S0108768184002354. Bibcode: 1984AcCrB..40..382F.
4. ↑ Valdés, Carlos; Toledo, Leticia M.; Spitz, Urs; Rebek, Julius (1996). "Structure and Selectivity of a Small Dimeric Encapsulating Assembly". Chem. Eur. J. 2 (8): 989–991. doi:10.1002/chem.19960020814.
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27. ↑ Worsch, Detlev; Vögtle, Fritz (2002). "Separation of enantiomers by clathrate formation". Topics in Current Chemistry. Springer-Verlag. pp. 21–41. doi:10.1007/bfb0003835. ISBN 3-540-17307-2.
28. ↑ Dai, Wenbo; Niu, Xiaowei; Wu, Xinghui; Ren, Yue; Zhang, Yongfeng; Li, Gengchen; Su, Han; Lei, Yunxiang et al. (2022-03-21). "Halogen Bonding: A New Platform for Achieving Multi-Stimuli-Responsive Persistent Phosphorescence" (in en). Angewandte Chemie International Edition 61 (13). doi:10.1002/anie.202200236. ISSN 1433-7851. PMID 35102661. https://onlinelibrary.wiley.com/doi/10.1002/anie.202200236.
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31. ↑ Zhu, Weijie; Xing, Hao; Li, Errui; Zhu, Huangtianzhi; Huang, Feihe (2022-11-08). "Room-Temperature Phosphorescence in the Amorphous State Enhanced by Copolymerization and Host–Guest Complexation" (in en). Macromolecules 55 (21): 9802–9809. doi:10.1021/acs.macromol.2c00680. ISSN 0024-9297. Bibcode: 2022MaMol..55.9802Z. https://pubs.acs.org/doi/10.1021/acs.macromol.2c00680.
32. ↑ 32.0 32.1 Ikura, Ryohei; Park, Junsu; Osaki, Motofumi; Yamaguchi, Hiroyasu; Harada, Akira; Takashima, Yoshinori (December 2022). "Design of self-healing and self-restoring materials utilizing reversible and movable crosslinks" (in en). NPG Asia Materials 14 (1): 10. doi:10.1038/s41427-021-00349-1. ISSN 1884-4049. Bibcode: 2022npjAM..14...10I.
33. ↑ 33.0 33.1 Xie, Jing; Yu, Peng; Wang, Zhanhua; Li, Jianshu (2022-03-14). "Recent Advances of Self-Healing Polymer Materials via Supramolecular Forces for Biomedical Applications" (in en). Biomacromolecules 23 (3): 641–660. doi:10.1021/acs.biomac.1c01647. ISSN 1525-7797. PMID 35199999. https://pubs.acs.org/doi/10.1021/acs.biomac.1c01647.
34. ↑ 34.0 34.1 Park, Junsu; Murayama, Shunsuke; Osaki, Motofumi; Yamaguchi, Hiroyasu; Harada, Akira; Matsuba, Go; Takashima, Yoshinori (October 2020). "Extremely Rapid Self-Healable and Recyclable Supramolecular Materials through Planetary Ball Milling and Host–Guest Interactions" (in en). Advanced Materials 32 (39). doi:10.1002/adma.202002008. ISSN 0935-9648. PMID 32844527. Bibcode: 2020AdM....3202008P. https://onlinelibrary.wiley.com/doi/10.1002/adma.202002008.
35. ↑ Wang, C. X.; Chen, Sh. L. (2005). "Fragrance-release Property of β-Cyclodextrin Inclusion Compounds and their Application in Aromatherapy". Journal of Industrial Textiles 34 (3): 157–166. doi:10.1177/1528083705049050.
36. ↑ Ellis-Davies, Graham C. R. (2007). "Caged compounds: Photorelease technology for control of cellular chemistry and physiology". Nature Methods 4 (8): 619–628. doi:10.1038/nmeth1072. PMID 17664946.
37. ↑ Blanco-Gómez, Arturo; Cortón, Pablo; Barravecchia, Liliana; Neira, Iago; Pazos, Elena; Peinador, Carlos; García, Marcos D. (2020). "Controlled binding of organic guests by stimuli-responsive macrocycles" (in en). Chemical Society Reviews 49 (12): 3834–3862. doi:10.1039/D0CS00109K. ISSN 0306-0012. PMID 32395726. http://xlink.rsc.org/?DOI=D0CS00109K.
38. ↑ Ju, Huaqiang; Zhu, Chao Nan; Wang, Hu; Page, Zachariah A.; Wu, Zi Liang; Sessler, Jonathan L.; Huang, Feihe (February 2022). "Paper without a Trail: Time-Dependent Encryption using Pillar[5arene-Based Host–Guest Invisible Ink"] (in en). Advanced Materials 34 (6). doi:10.1002/adma.202108163. ISSN 0935-9648. PMID 34802162. Bibcode: 2022AdM....3408163J. https://onlinelibrary.wiley.com/doi/10.1002/adma.202108163.
39. ↑ Hou, Yali; Zhang, Zeyuan; Lu, Shuai; Yuan, Jun; Zhu, Qiangyu; Chen, Wei-Peng; Ling, Sanliang; Li, Xiaopeng et al. (2020-11-04). "Highly Emissive Perylene Diimide-Based Metallacages and Their Host–Guest Chemistry for Information Encryption" (in en). Journal of the American Chemical Society 142 (44): 18763–18768. doi:10.1021/jacs.0c09904. ISSN 0002-7863. PMID 33085462. Bibcode: 2020JAChS.14218763H. https://pubs.acs.org/doi/10.1021/jacs.0c09904.
40. ↑ Jin, Jia-Ni; Yang, Xi-Ran; Wang, Yan-Fang; Zhao, Lei-Min; Yang, Liu-Pan; Huang, Liping; Jiang, Wei (2023-01-18). "Mechanical Training Enabled Reinforcement of Polyrotaxane-Containing Hydrogel". Angewandte Chemie 135 (8). doi:10.1002/ange.202218313. ISSN 0044-8249. Bibcode: 2023AngCh.135E8313J.
41. ↑ Wang, Shuaipeng; Chen, Yong; Sun, Yonghui; Qin, Yuexiu; Zhang, Hui; Yu, Xiaoyong; Liu, Yu (2022-01-20). "Stretchable slide-ring supramolecular hydrogel for flexible electronic devices" (in en). Communications Materials 3 (1): 2. doi:10.1038/s43246-022-00225-7. ISSN 2662-4443. Bibcode: 2022CoMat...3....2W.
42. ↑ Huang, Zehuan; Chen, Xiaoyi; O'Neill, Stephen J. K.; Wu, Guanglu; Whitaker, Daniel J.; Li, Jiaxuan; McCune, Jade A.; Scherman, Oren A. (January 2022). "Highly compressible glass-like supramolecular polymer networks" (in en). Nature Materials 21 (1): 103–109. doi:10.1038/s41563-021-01124-x. ISSN 1476-1122. PMID 34819661. Bibcode: 2022NatMa..21..103H. https://www.nature.com/articles/s41563-021-01124-x.
43. ↑ Biavardi, Elisa (February 14, 2011). "Exclusive recognition of sarcosine in water and urine by a cavitand-functionalized silicon surface". Proceedings of the National Academy of Sciences of the United States of America 109 (7): 2263–2268. doi:10.1073/pnas.1112264109. PMID 22308349. Bibcode: 2012PNAS..109.2263B.
44. ↑ de Silva, A.P.; McCaughan, B; McKinney, B.O. F.; Querol, M. (2003). "Newer optical-based molecular devices from older coordination chemistry". Dalton Transactions 10 (10): 1902–1913. doi:10.1039/b212447p.
45. ↑ Anslyn, E. (2007). "Supramolecular Analytical Chemistry". Journal of Organic Chemistry 72 (3): 687–699. doi:10.1021/jo0617971. PMID 17253783.
46. ↑ Nguyen, B.; Anslyn, E. (2006). "Indicator-displacement assays". Coord. Chem. Rev. 250 (23–24): 3118–3127. doi:10.1016/j.ccr.2006.04.009.
47. ↑ Yang, V.; Fu, Y.; Teng, C.; Ma, S.; Shanberge, J. (1994). "A method for the quantitation of protamine in plasma". Thrombosis Research 74 (4): 427–434. doi:10.1016/0049-3848(94)90158-9. PMID 7521974. https://deepblue.lib.umich.edu/bitstream/2027.42/31577/1/0000505.pdf.
48. ↑ Eggleston, A.; Rahim, N.; Kowalczykowski, S; Ma, S.; Shanberge, J. (1996). "A method for the quantitation of protamine in plasma". Nucleic Acids Research 24 (7): 1179–1186. doi:10.1093/nar/24.7.1179. PMID 8614617.
49. ↑ Biancardi, Alessandro; Tarita, Biver; Alberto, Marini; Benedetta, Mennucci; Fernando, Secco (2011). "Thiazole orange (TO) as a light-switch probe: a combined quantum-mechanical and spectroscopic study". Physical Chemistry Chemical Physics 13 (27): 12595–12602. doi:10.1039/C1CP20812H. PMID 21660321. Bibcode: 2011PCCP...1312595B.
50. ↑ Atwood, J; Barbour, L; Jerga, A; Schottel, L (2002). "Guest Transport in a nonporous Organic Solid via Dynamic van der Waals Cooperativity". Science 298 (5595): 1000–1002. doi:10.1126/science.1077591. PMID 12411698. Bibcode: 2002Sci...298.1000A.
51. ↑ Kitagawa, S; Uemura, K (2005). "Dynamic porous properties of coordination polymers inspired by hydrogen bonds". Chemical Society Reviews 34 (2): 109–119. doi:10.1039/b313997m. PMID 15672175.
52. ↑ Sozzani, P; Bracco, S; Commoti, A; Ferretti, R; Simonutti, R (2005). "Methane and Carbon Dioxide Storage in a Porous van der Waals Crystal". Angewandte Chemie 44 (12): 1816–1820. doi:10.1002/anie.200461704. PMID 15662674.
53. ↑ Uemura, K; Kitagawa, S; Fukui, K; Saito, K (2004). "A Contrivance for a Dynamic Porous Framework: Cooperative Guest Adsorption Based on Square Grids Connected by Amide−Amide Hydrogen Bonds". J. Am. Chem. Soc. 126 (12): 3817–3828. doi:10.1021/ja039914m. PMID 15038736. Bibcode: 2004JAChS.126.3817U.
54. ↑ Dobrzanska, L; Lloyd, G; Esterhuysen, C; Barbour, L (2006). "Guest-Induced Conformational Switching in a Single Crystal". Angewandte Chemie 45 (35): 5856–5859. doi:10.1002/anie.200602057. PMID 16871642.
55. ↑ Eric Hughes; Jason Jordan; Terry Gullion (2001). "Structural Characterization of the [Cs(p-tert-butylcalix[4]arene -H) (MeCN)] Guest–Host System by 13C-133Cs REDOR NMR". Journal of Physical Chemistry B 105 (25): 5887–5891. doi:10.1021/jp004559x.
56. ↑ Serkan Erdemir; Mufit Bahadir; Mustafa Yilmaz (2009). "Extraction of Carcinogenic Aromatic Amines from Aqueous Solution Using Calix[n]arene Derivatives as Carriers". Journal of Hazardous Materials 168 (2–3): 1170–1176. doi:10.1016/j.jhazmat.2009.02.150. PMID 19345489. Bibcode: 2009JHzM..168.1170E.
57. ↑ Alcohol powder: Alcopops from a bag , Westdeutsche Zeitung, 28 October 2004 (German)
58. ↑ Preparation of an Alcohol Containing Powder, General Foods Corporation March 31, 1972

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