Dynamic covalent synthesis

Cougnon, Fabien B. L.; Stefankiewicz, Artur R.; Ulrich, Sébastien

doi:10.1039/d3sc05343a

Cited by 19 publications

(8 citation statements)

References 170 publications

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“…Finally, a major feature of the present work resides in the interplay between the intrinsic dynamism of CDC and molecular assemblies potentially of prebiotic significance , to map how reaction networks adapt and organize on changing environmental conditions. The present systems provide insight into the initial steps of the build-up of complexity , toward living cells in the long perspective. ,, …”

Section: Discussionmentioning

confidence: 99%

Triple Adaptation of Constitutional Dynamic Networks of Imines in Response to Micellar Agents: Internal Uptake–Interfacial Localization–Shape Transition

Rieu,

Osypenko,

Lehn

2024

J. Am. Chem. Soc.

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Understanding the behavior of complex chemical reaction networks and how environmental conditions can modulate their organization as well as the associated outcomes may take advantage of the design of related artificial systems. Microenvironments with defined boundaries are of particular interest for their unique properties and prebiotic significance. Dynamic covalent libraries (DCvLs) and their underlying constitutional dynamic networks (CDNs) have been shown to be appropriate for studying adaptation to several processes, including compartmentalization. However, microcompartments (e.g., micelles) provide specific environments for the selective protection from interfering reactions such as hydrolysis and an enhanced chemical promiscuity due to the interface, governing different processes of network modulation. Different interactions between the micelles and the library constituents lead to dynamic sensing, resulting in different expressions of the network through pattern generation. The constituents integrated into the micelles are protected from hydrolysis and hence preferentially expressed in the network composition at the cost of constitutionally linked members. In the present work, micellar integration was observed for two processes: internal uptake based on hydrophobic forces and interfacial localization relying on attractive electrostatic interactions. The latter drives a complex triple adaptation of the network with feedback on the shape of the self-assembled entity. Our results demonstrate how microcompartments can enforce the expression of constituents of CDNs by reducing the hydrolysis of uptaken members, unravelling processes that govern the response of reactions networks. Such studies open the way toward using DCvLs and CDNs to understand the emergence of complexity within reaction networks by their interactions with microenvironments.

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Section: Discussionmentioning

confidence: 99%

Triple Adaptation of Constitutional Dynamic Networks of Imines in Response to Micellar Agents: Internal Uptake–Interfacial Localization–Shape Transition

Rieu,

Osypenko,

Lehn

2024

J. Am. Chem. Soc.

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“…This study therefore extends the scope of the growing class of dynamic covalent materials. [54][55][56][57][58][59][60][61][62][63][64] In future work, we aim to explore the functional properties of this inside/outside functionalized SWCNT material.…”

Section: Methodsmentioning

confidence: 99%

Simultaneous Inside and Outside Functionalization of Single‐Walled Carbon Nanotubes

Kraus,

Meingast,

Hald

et al. 2024

Angew Chem Int Ed

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Functionalizing single‐walled carbon nanotubes (SWCNTs) in a robust way that does not affect the sp2 carbon framework is a considerable research challenge. Here we describe how triiodide salts of positively charged macrocycles can be used not only to functionalize SWCNTs from the outside, but simultaneously from the inside. We employed disulfide exchange in aqueous solvent to maximize the solvophobic effect and therefore achieve a high degree of macrocycle immobilization. Characterization by Raman spectroscopy, EDX‐STEM and HR‐TEM clearly showed that serendipitously this wet‐chemical functionalization protocol also led to the encapsulation of polyiodide chains inside the nanotubes. The resulting three‐shell composite materials are redoxactive and experience an intriguing interplay of electrostatic, solvophobic and mechanical effects that could be of interest for applications in energy storage.

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“…Diese Studie erweitert daher den Anwendungsbereich der wachsenden Klasse der dynamischen kovalenten Materialien. [54][55][56][57][58][59][60][61][62][63][64] In zukünftigen Arbeiten wollen wir die funktionellen Eigenschaften dieses innen/außen funktionalisierten SWCNT-Materials untersuchen.…”

Section: Um Einwandige Kohlenstoff-nanoröhren (Swcnts) Inunclassified

Simultane Funktionalisierung von Einwandigen Kohlenstoff‐Nanoröhren von Innen und Außen

Kraus,

Meingast,

Hald

et al. 2024

Angewandte Chemie

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Dynamic covalent synthesis

Abstract: Toward organic self-synthesis using encoded synthons and programmed processes: we summarize here the design principles and the recent achievements which illustrate the power of dynamic covalent synthesis for making complex covalent architectures.

Cited by 19 publications

References 170 publications

Triple Adaptation of Constitutional Dynamic Networks of Imines in Response to Micellar Agents: Internal Uptake–Interfacial Localization–Shape Transition

Triple Adaptation of Constitutional Dynamic Networks of Imines in Response to Micellar Agents: Internal Uptake–Interfacial Localization–Shape Transition

Simultaneous Inside and Outside Functionalization of Single‐Walled Carbon Nanotubes

Simultane Funktionalisierung von Einwandigen Kohlenstoff‐Nanoröhren von Innen und Außen

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