Orthogonal Dynamic Covalent and Non‐covalent Reactions

Zhang, Dan‐Wei; Li, Zhan‐Ting

doi:10.1002/9781119075738.ch5

Cited by 25 publications

(39 citation statements)

References 100 publications

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“…Having prepared imine-linked precursor 3 we investigated its reactivity under alkyne metathesis conditions. Given the lack of examples of imine functionality in AM,42 a key consideration was the selection of an appropriate metathesis catalyst. Zhang and co-workers have demonstrated that tridentate, phenol-based supporting ligands generate highly active and functionally tolerant molybdenum metathesis catalysts 44,45,51.…”

Section: Resultsmentioning

confidence: 99%

“…DCC employs reversible covalent bonds to self-assemble complex structures from simpler building blocks 10. The DCC toolbox comprises a number of orthogonal reactions,11 including alkyne/olefin metathesis,2,3 and imine/hydrazone,12–18 boronic ester19–21 and disulfide/dithioacetal exchange 22–28. Orthogonality in DCC is frequently leveraged in dynamic combinatorial library synthesis, where modification of reaction conditions ( e.g.…”

Section: Introductionmentioning

confidence: 99%

“…1A). 7–9,39–41 After surveying the literature, we were motivated by the apparent lack of examples combining alkyne metathesis with orthogonal dynamic chemistries in multitopic DCC 42,43. The development of highly active and functional group tolerant AM catalysts further demonstrates that this methodology is poised to expand into new chemical space 1,6,44–51.…”

Section: Introductionmentioning

confidence: 99%

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A tetrahedral molecular cage with a responsive vertex

Pattillo

Moore

2019

Chem. Sci.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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A tetrahedral molecular cage with a responsive vertex

Pattillo

Moore

2019

Chem. Sci.

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“…Theu nderlying (covalent) chemical transformations, however, have been very simple;t he role of the fuel is generally the formation of as ingle unstable covalent bond. This simplicity contrasts sharply with the sophistication of dynamic systems under thermodynamic control, in which the simultaneous formation of many covalent bonds [25,26] can be used to self-assemble macrocycles, [27][28][29] cages, [30][31][32][33][34] ladders, [35,36] knots, [37][38][39] and other closed architectures. [40][41][42] This structural complexity leads to new function.…”

Section: Introductionmentioning

confidence: 99%

Dissipative Assembly of Macrocycles Comprising Multiple Transient Bonds

2020

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Dissipative assembly has great potential for the creation of new adaptive chemical systems.H owever,w hile molecular assembly at equilibrium is routinely used to prepare complex architectures from polyfunctional monomers,species formed out of equilibrium have,tothis point, been structurally very simple.I nm ost examples the fuel simply effects the formation of as ingle short-lived covalent bond. Herein, we show that chemical fuels can assemble bifunctional components into macrocycles containing multiple transient bonds. Specifically,d icarboxylic acids give aqueous dianhydride macrocycles on treatment with ac arbodiimide.T he macrocycles are assembled efficiently as aconsequence of both fueldependent and fuel-independent mechanisms;t hey undergo slower decomposition, building up as the fuel recycles the components,a nd are af avored product of the dynamic exchange of the anhydride bonds.T hese results create new possibilities for generating structurally sophisticated out-ofequilibrium species.

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“…Based on the breakage and formation of dynamic covalent bonds, the molecule can respond to outside stimulus (light, pH, temperature, electric fields, etc.) through the inter-/intramolecular interaction. − The dynamic processes have been applied in receptor synthesis, catalysts, biomacromolecule recognition, sensors, and self-healing polymers. − …”

Section: Introductionmentioning

confidence: 99%

Interactive Aggregation-Induced Emission Systems Controlled by Dynamic Covalent Chemistry

Ding

Che

et al. 2019

J. Org. Chem.

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Aggregation-induced emission (AIE) molecules show all kinds of application in biological research, chemical sensing, and medical study. However, most of the reported molecules are based on the performance of the single molecular entity. In this paper, a molecular system for real-time sensing through combination of dynamic covalent chemistry and aggregation-induced emission was rationally designed and tested. The aggregated particles exhibit different fluorescence emission colors upon the addition of various kinds of chemical reagents. The LC–MS analysis reveals that the breakage, formation, and exchange of the disulfide bonds in the molecular system occur spontaneously upon different reagents (base/acid and cysteine), which leads to a change in the proportion of different components in the system accordingly. Meanwhile, the fluorescence emission of the AIE system exhibits blue/red shift accompanied by intensity changes. Moreover, the particle size of the aggregated molecules gradually increased with the change of the chemical environment, which could be the result of the nucleus growing through intermolecular hydrogen bonding among molecular components. Thus, the chemical environment change results in the interactions of molecules, which further leads to the variation of dynamic fluorescence emission and morphology. The result represents a promising future for a dynamic AIE molecular system in the bioimaging and sensing study.

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Orthogonal Dynamic Covalent and Non‐covalent Reactions

Cited by 25 publications

References 100 publications

A tetrahedral molecular cage with a responsive vertex

A tetrahedral molecular cage with a responsive vertex

Dissipative Assembly of Macrocycles Comprising Multiple Transient Bonds

Interactive Aggregation-Induced Emission Systems Controlled by Dynamic Covalent Chemistry

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