Supramolecular systems constructed by crown ether-based cryptands

Ren, Xintong; Zhang, Jing; Cheng, Ming; Wang, Qi; Jiang, Juli; Wang, Leyong

doi:10.1016/j.tetlet.2018.04.056

Cited by 14 publications

(4 citation statements)

References 46 publications

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“…and they are capable of forming host-guest complexes [ 17 , 18 , 19 , 20 ]. Pillar[5]arenes are able to form various types of self-organizing structures depending on the used solvent: supramolecular polymers, supramolecular nodes and rotaxanes [ 21 , 22 , 23 , 24 , 25 , 26 ], and solid lipid nanoparticles (SLN) [ 27 , 28 ]. Initially, SLN are prepared from mixtures of lipids (hydrophobic or amphiphilic molecule, soluble in organic solvents) with, if needed, the presence of cosurfactants [ 29 ].…”

Section: Introductionmentioning

confidence: 99%

Surfactant Effect on the Physicochemical Characteristics of Solid Lipid Nanoparticles Based on Pillar[5]arenes

Nazarova

Yakimova

Filimonova

et al. 2022

IJMS

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Novel monosubstituted pillar[5]arenes containing both amide and carboxyl functional groups were synthesized. Solid lipid nanoparticles based on the synthesized macrocycles were obtained. Formation of spherical particles with an average hydrodynamic diameter of 250 nm was shown for pillar[5]arenes containing N-(amidoalkyl)amide fragments regardless of their concentration. It was established that pillar[5]arene containing N-alkylamide fragments can form spherical particles with two different sizes (88 and 223 nm) depending on its concentration. Mixed solid lipid nanoparticles based on monosubstituted pillar[5]arenes and surfactant (dodecyltrimethylammonium chloride) were obtained for the first time. The surfactant made it possible to level the effect of the macrocycle concentration. It was found that various types of aggregates are formed depending on the macrocycle/surfactant ratio. Changing the macrocycle/surfactant ratio allows to control the charge of the particles surface. This controlled property will lead to the creation of molecular-scale porous materials that selectively interact with various types of substrates, including biopolymers.

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Section: Introductionmentioning

confidence: 99%

Surfactant Effect on the Physicochemical Characteristics of Solid Lipid Nanoparticles Based on Pillar[5]arenes

Nazarova

Yakimova

Filimonova

et al. 2022

IJMS

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“…In addition to the use of these parent derivatives in the analytical and synthetic chemistry fields, various kinds of functionalized derivatives have been synthesized for advanced functions such as fluorescence signaling . The cavity sizes of the cryptands can be expanded by replacing the bridgehead nitrogen atoms with benzene rings; these larger analogues are capable of binding with organic molecules in addition to metal cations . Some cryptand molecules are used for the wheel component of rotaxanes and related interlocked molecules. − Cryptand derivatives that can bind anions have also been developed by the use of suitable anion-interacting motifs .…”

Section: Introductionmentioning

confidence: 99%

“…The cavity sizes of the cryptands can be expanded by replacing the bridgehead nitrogen atoms with benzene rings; these larger analogues are capable of binding with organic molecules in addition to metal cations . Some cryptand molecules are used for the wheel component of rotaxanes and related interlocked molecules. − Cryptand derivatives that can bind anions have also been developed by the use of suitable anion-interacting motifs . The chemistry of the cryptand-like bicyclic structures has now been expanded to cover organic cages that can accommodate larger organic guest species …”

Section: Introductionmentioning

confidence: 99%

Enhancement of Alkali Metal Ion Recognition by Metalation of a Tris(saloph) Cryptand Having Benzene Rings at the Bridgeheads

2021

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A cryptand derivative, H6L, which has three H2saloph arms connected by two benzene ring bridgeheads, was synthesized and converted into the trinuclear metallocryptand, LNi3. The nonmetalated host, H6L, was found to bind to alkali metal ions (Na+, K+, Rb+, Cs+; logK a = 3.37–6.67) in its well-defined cavity in DMSO/chloroform (1:9). The binding affinity was enhanced by 1–2 orders of magnitude upon the conversion into the metallocryptand, LNi3, which can be explained by the more polarized phenoxo groups in the [Ni(saloph)] arms. The guest binding affinity of Na+ < K+ < Rb+ ≈ Cs+ was clearly demonstrated by the 1H NMR competition experiments. The DFT calculations suggested that the Rb+ ion most suitably fit into the benzene–benzene spacing with a cation−π interaction and that only the largest Cs+ ion can almost equally interact with all six phenoxo oxygen donor atoms. The metallocryptand, LNi3, also showed a strong binding affinity to Ag+ by taking advantage of cation−π interactions, which was confirmed by spectroscopic titrations and crystallographic analysis as well as DFT calculations. Thus, the well-defined three-dimensional cavity of LNi3 was found to be suitable for strong binding with alkali metal ions as well as Ag+.

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“…Based on the above construction strategies and the facile modifications of crown ethers, the preparation and function studies of CSPs have attracted much attention from researchers in recent decades. Wang and co-workers [17,18] and Yin and co-workers [19] shortly introduced the structures and constructions of CSPs, respectively. Huang and co-workers comprehensively reviewed the research process for CSPs in an earlier year.…”

Section: Introductionmentioning

confidence: 99%

Crown Ether‐Based Supramolecular Polymers: From Synthesis to Self‐Assembly

Duan

Huang

et al. 2021

Macromol. Rapid Commun.

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Supramolecular polymers not only possess many advantages of traditional polymers, but also have many unique characteristics. Supramolecular polymers can be constructed by self-assembly of various noncovalent interactions. Host-guest interaction, as one important type of noncovalent interactions, has been widely applied to construct supramolecular polymers. From the perspective of classification of the recognition system motifs, host-guest recognition motifs mainly include crown ether, cyclodextrin, calixarene, cucurbituril, and pillararene-based host-guest recognition pairs. Crown ethers, as the first-generation macrocyclic hosts, have played a very important part in the development of supramolecular chemistry. Due to the easy modification of crown ethers, various crown ether derivatives have been prepared by attaching some functional groups to the edges of crown ethers, which endowed them with some interesting properties and made them ideal candidates for the fabrication of supramolecular polymers. This review gives a review of the preparation of crown ether-based supramolecular polymers (CSPs) and summarizes crown ether-based recognition pairs, organization methods, topological structures, stimuli-responsiveness, and functional characteristics.

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Supramolecular systems constructed by crown ether-based cryptands

Cited by 14 publications

References 46 publications

Surfactant Effect on the Physicochemical Characteristics of Solid Lipid Nanoparticles Based on Pillar[5]arenes

Surfactant Effect on the Physicochemical Characteristics of Solid Lipid Nanoparticles Based on Pillar[5]arenes

Enhancement of Alkali Metal Ion Recognition by Metalation of a Tris(saloph) Cryptand Having Benzene Rings at the Bridgeheads

Crown Ether‐Based Supramolecular Polymers: From Synthesis to Self‐Assembly

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