Template effects of vesicles in dynamic covalent chemistry

Bravin, Carlo; Hunter, Christopher A.

doi:10.1039/d0sc03185b

Cited by 22 publications

(20 citation statements)

References 48 publications

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“…Moreover, as in most of the cases a complete quantification of the species in equilibrium could be achieved, then calculation of the corresponding equilibrium constants was trivial (Table 2 ). Curiously, there are scarce papers about dynamic covalent reactions where the equilibrium constants of the exchanges are calculated,[ 71 , 72 ] even when it is a key physico‐chemical property for a reversible process and it provides a great deal of information.…”

Section: Resultsmentioning

confidence: 99%

Dynamic Nucleophilic Aromatic Substitution of Tetrazines

et al. 2021

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A dynamic nucleophilic aromatic substitution of tetrazines (SNTz) is presented herein. It combines all the advantages of dynamic covalent chemistry with the versatility of the tetrazine moiety. Indeed, libraries of compounds or sophisticated molecular structures can be easily obtained, which are susceptible to post‐functionalization by inverse electron demand Diels–Alder (IEDDA) reaction, which also locks the exchange. Additionally, the structures obtained can be disassembled upon the application of the right stimulus, either UV irradiation or a suitable chemical reagent. Moreover, SNTz is compatible with the imine chemistry of anilines. The high potential of this methodology has been proved by building two responsive supramolecular systems: A macrocycle that displays a light‐induced release of acetylcholine; and a truncated [4+6] tetrahedral shape‐persistent fluorescent cage, which is disassembled by thiols unless it is post‐stabilized by IEDDA.

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Section: Resultsmentioning

confidence: 99%

Dynamic Nucleophilic Aromatic Substitution of Tetrazines

et al. 2021

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“…4), and the resulting equilibrium constant of (1.0 AE 0.3 Â 10 5 M À1 ) is similar to the value measured previously by direct titration (2.0 AE 0.2 Â 10 5 M À1 ). 34 The data in Fig. 4 show that the intensity of the uorescence response obtained from this system is directly proportional to the concentration of Michael adduct formed in the lipid bilayer membrane.…”

Section: Mechanism Of Signal Transductionmentioning

confidence: 87%

Artificial transmembrane signal transduction mediated by dynamic covalent chemistry

2021

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“…45 In the presence of lipid bilayer vesicles, DCLs may be biased in favour of one product over another. This is driven either by differing membrane partitioning of library members, as demonstrated by Bravin and Hunter, 46 This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.…”

Section: Dynamic Combinatorial Chemistry In Lipid Bilayer Vesiclesmentioning

confidence: 99%