Dynamic Covalent Chemistry for Synthetic Molecular Machines

Liu, Yi; Leung, Ken Cham‐Fai

doi:10.1002/9781119075738.ch7

Cited by 5 publications

(14 citation statements)

References 82 publications

(66 reference statements)

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“…1 H NMR (500 MHz, CDCl 3 ) δ 7.10 (d, J = 8.8 Hz, 4H), 6.84 (d, J = 8.9 Hz, 4H), 3.79 (s, 6H). 13 Bis(4-trifluoromethylphenyl)carbodiimide. In an oven-dried flask, 4-trifluorophenyl isocyanate (2.00 mL, 19.3 mmol, 1.0 equiv.)…”

Section: Methodsmentioning

confidence: 99%

“…1 H NMR (500 MHz, CDCl 3 ) δ 7.60 (d, J = 8.3 Hz, 4H), 7.27 (d, J = 8.3 Hz, 4H). 13 C{ 1 H} NMR (126 MHz, CDCl 3 ) δ 141.3, 133.5, 128.2 (q, J = 32.9 Hz), 127.0 (q, J = 3.7 Hz), 124.7, 124.0 (q, J = 271. N-(4-Methylbenzyl)-N′-(p-tolyl)carbodiimide.…”

Section: Methodsmentioning

confidence: 99%

“…1 H NMR (500 MHz, CDCl 3 ) δ 7.03 (d, J = 7.8 Hz, 4H), 6.94-6.62 (m, 4H), 4.18-4.02 (m, 1H), 3.64 (dt, J = 13.5, 3.1 Hz, 1H), 2.97 (td, 12.9, 2.6 Hz, 1H), 2.27 (s, 6H), 1.66-1.45 (m, 5H), 1.32 (dt, J = 12.3, 2.3 Hz, 1H), 1.18 (d, J = 6.9 Hz, 3H). 13 2,6-Dimethyl-N,N′-di-p-tolylpiperidine-1-carboximidamide (G3). Product was a white powder.…”

Section: Methodsmentioning

confidence: 99%

“…1 H NMR (500 MHz, CDCl 3 ) δ 7.13-6.88 (m, 4H), 6.91-6.54 (m, 4H), 4.15-3.89 (m, 2H), 2.26 (s, 6H), 1.95-1.73 (m, 1H), 1.72-1.61 (m, 2H), 1.55-1.33 (m, 3H), 1.28 (d, J = 6.8 Hz, 6H). 13 N,N′-Di-p-tolylmorpholine-4-carboximidamide (G4). Product was a glassy solid.…”

Section: Methodsmentioning

confidence: 99%

“…The system thus continuously adapts to changes in its environment, leading to the widespread use of DCC to create stimuli-responsive, adaptable materials. [3][4][5][6][7] Thermodynamic control in DCC can also result in self-assembly of large, complex nanostructures such as covalent organic frameworks, [8][9][10][11][12] molecular machines, 13 and molecular cages. [14][15][16][17] Other applications of DCC include the generation of self-sorting libraries of compounds, 18 adaptable drug delivery platforms, 19 and responsive biomaterials.…”

Section: Introductionmentioning

confidence: 99%

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Thermodynamic, kinetic, and mechanistic studies of the thermal guanidine metathesis reaction

et al. 2022

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Thermodynamic, kinetic, and mechanistic studies of the thermal guanidine metathesis reaction

et al. 2022

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Dissipative Dynamic Covalent Chemistry (DDCvC) Based on the Transimination Reaction

Valentini

Melchiorre

Spatola

et al. 2022

Chemistry A European J

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This work reports that the composition of a dynamic library (DL) of interconverting imines can be controlled over time in a dissipative fashion by the addition of an activated carboxylic acid used as a chemical fuel. When the fuel is added to the DL, which is initially under thermodynamic equilibrium, the composition of the mixture dramatically changes and a new, dissipative (out of equilibrium) state is reached that persists until fuel exhaustion. Thus, a transient dissipative dynamic library (DDL) is generated that, eventually, reverts back to the initial DL when the fuel is consumed, closing a DL→DDL→DL cycle. The larger the amount of added fuel, the longer the time spent by the system in the DDL state. The transimination reaction is shown to be an optimal candidate for the realization of a dissipative dynamic covalent chemistry (DDCvC).

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Dynamic Covalent Chemistry for Synthesis and Co‐conformational Control of Mechanically Interlocked Molecules

Gaedke

Schaufelberger

2022

Eur J Org Chem

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Mechanically interlocked molecules have found extensive applications in areas all across the physical sciences, from materials to catalysis and sensing. However, introducing mechanical bonds and entanglements at the molecular level is still a significant challenge due to the inherent restriction in entropy needed to preorganize strands before interlocking. Over the last decade, dynamic covalent chemistry has emerged as one of the most efficient methods of forming rotaxanes, catenanes and molecular knots. By using reversible bonds such as imines, disulfides and boronate esters, one can use the inherent error‐correction in these linkages to form interlocked architectures with high fidelity and often in excellent yields. This review reports on recent advances in the use of dynamic covalent chemistry to make mechanically interlocked molecules, systematically surveying clipping, capping and templating approaches with dynamic bonds. Furthermore, it is also discussed how dynamic bonds can be used to control motion, co‐conformational expression and catalytic activity in mechanically interlocked molecular machinery.

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Dynamic Covalent Chemistry for Synthetic Molecular Machines

Cited by 5 publications

References 82 publications

Thermodynamic, kinetic, and mechanistic studies of the thermal guanidine metathesis reaction

Thermodynamic, kinetic, and mechanistic studies of the thermal guanidine metathesis reaction

Dissipative Dynamic Covalent Chemistry (DDCvC) Based on the Transimination Reaction

Dynamic Covalent Chemistry for Synthesis and Co‐conformational Control of Mechanically Interlocked Molecules

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