Metal Coordination Guided Formation of Discrete Neutral Three-Component Hydrogen-Bonded Architectures

Ye, Chuang; Yuan, Wei; Wei, Xin; Liang, Rongzu; Naitė, Augustina Jozeliu; Mendoza, Javier de; Orentas, Edvinas; Shi, Qixun

doi:10.1021/acs.orglett.0c03397

Cited by 3 publications

(6 citation statements)

References 35 publications

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“…The use of a diastereomeric mixture of DAN had no effect on the overall symmetry of the spectrum; the nonbranched analogue DAN 1 (R 2 = n -pentyl, Figure d) gave an identical set of resonances in the NMR spectrum (Figure S43), indicating the absence of stereochemical communication between the peripheral DAN substituents and the chiral bicyclic core …”

Section: Results and Discussionmentioning

confidence: 99%

“…The use of a diastereomeric mixture of DAN had no effect on the overall symmetry of the spectrum; the nonbranched analogue DAN 1 (R 2 = n-pentyl, Figure 2d) gave an identical set of resonances in the NMR spectrum (Figure S43), indicating the absence of stereochemical communication between the peripheral DAN substituents and the chiral bicyclic core. 53 Having accomplished successful noncovalent synthesis of a supramolecular tweezer, we further sought to explore its dynamic and structural features to control the topology of the aggregates via external stimuli.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Fully Supramolecular Chiral Hydrogen-Bonded Molecular Tweezer

et al. 2022

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Molecular tweezers are open-ended, cavity-possessing U-shaped molecular architectures with high potential for various applications in supramolecular chemistry. Their covalent synthesis, however, is often tedious and the structures obtained lack structural responsiveness beyond the limited conformational flexibility of the scaffold. Herein we present a proof-of-concept study on the design, synthesis, assembly, and transformations of a novel supramolecular constructa fully noncovalent molecular tweezer. The supramolecular tweezer was assembled from a set of four building blocks, composed of two identical molecular angle bars and two flat aromatic extension wings, using hydrogen bonding only. The chirality-assisted aggregation process was utilized to ensure scaffold bending directionality using enantiomerically pure bicyclic angle bars. To address the challenges associated with shifting of the equilibrium from strong cooperative narcissistic self-sorting of self-complementary angle bars in cyclic aggregates toward integrative self-sorting in molecular tweezers, a rational desymmetrization strategy was applied. The dynamic supramolecular tweezer has been shown to display rich supramolecular chemistry, allowing for stimuli-responsive change in aggregate topology and solvent-responsive supramolecular polymerization.

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Section: Results and Discussionmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

Fully Supramolecular Chiral Hydrogen-Bonded Molecular Tweezer

et al. 2022

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“…The star-shaped derivatives of bile acid with UPy end groups (70, Figure 23) were shown to form micelles in DMSO with the nonpolar cholic acid skeletons in the micellar Cyclic three-component molecular complexes were constructed by quadruple Hbond formation between dimeric UPy units (65) and bis-amido-naphthyridines (66) decorated with ligands capable of binding metals. By the addition of neutral Pd-precursors, 65 2 66 4 Pd 2 -type cyclic complexes were formed [82]. A combination of metal coordination and self-assembly of UPy motifs led to the construction of tetrahedral cages from bipyridine derivative 67 and Fe 2+ or Zn 2+ ions, even in polar solvents, such as in acetonitrile and methanol [83].…”

Section: Formation Of Different Molecular Architectures Via Supramole...mentioning

confidence: 99%

“…Similar systems based on dimeric UPy-dibenzyl-anthracene (80) [106] or UPy-tetra-phenylethylene units (81) [107] were developed that could be assembled to nanoparticles in aqueous media in the presence of surfactants. Upon the addition of different ratios of energy acceptors, e.g., a benzothiadiazole derivative (82) in the latter case, tunable emittance could be achieved. Molecules 2023, 28, x FOR PEER REVIEW 28 Polymers constructed of multivalent UPy monomers capable of non-covalen gregation-induced emission were used for light-harvesting purposes.…”

Section: Electrochemical and Photochemical Applicationsmentioning

confidence: 99%

Urea-Functionalized Heterocycles: Structure, Hydrogen Bonding and Applications

Keszei,

Váradi,

Skoda-Földes

2023

Molecules

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Ureido-heterocycles exhibiting different triple- and quadruple H-bonding patterns are useful building blocks in the construction of supramolecular polymers, self-healing materials, stimuli-responsive devices, catalysts and sensors. The heterocyclic group may provide hydrogen bond donor/acceptor sites to supplement those in the urea core, and they can also bind metals and can be modified by pH, redox reactions or irradiation. In the present review, the main structural features of these derivatives are discussed, including the effect of tautomerization and conformational isomerism on self-assembly and complex formation. Some examples of their use as building blocks in different molecular architectures and supramolecular polymers, with special emphasis on biomedical applications, are presented. The role of the heterocyclic functionality in catalytic and sensory applications is also outlined.

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“…The dynamic and reversible metal coordination bond endows the material with stimulus, 96 while repeated fracture and healing at the molecular level can effectively dissipate energy. Therefore, the introduction of metal‐coordination bond into the material improves the self‐healing performance as well as mechanical strength of the composites 97 …”

Section: Dynamic Covalent Bondmentioning

confidence: 99%

Recent progress of biomass based self‐healing polymers

Song

Kou

et al. 2021

J of Applied Polymer Sci

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Self‐healing polymer materials have been developed rapidly over the past 20 years, which can replace thermosetting materials to a certain extent, repair damage without manual intervention, prolong service life, and compress usage cost. The self‐healing polymer materials derived from biomass resources can reduce the dependence on traditional non‐renewable resources such as petroleum. The structures and properties of biomass based self‐healing polymer materials are of great significance for their processing, recycling and self‐healing. In this paper, the research progress of bio‐based self‐healing polymer materials based on dynamic non‐covalent bonds and dynamic covalent bonds including hydroxyl ester, Schiff base, disulfide bond, and hydroxyl urethane derived from vegetable oil, lignin, cellulose, vanillin and natural rubber were reviewed, and the dynamic non‐covalent bonds and dynamic covalent bonds were also introduced. The applications of various dynamic covalent bonds and dynamic non‐covalent bonds in the design and construction of polymer materials were reviewed, and the future development of dynamic covalent polymer materials was prospected.

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Metal Coordination Guided Formation of Discrete Neutral Three-Component Hydrogen-Bonded Architectures

Cited by 3 publications

References 35 publications

Fully Supramolecular Chiral Hydrogen-Bonded Molecular Tweezer

Fully Supramolecular Chiral Hydrogen-Bonded Molecular Tweezer

Urea-Functionalized Heterocycles: Structure, Hydrogen Bonding and Applications

Recent progress of biomass based self‐healing polymers

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