Simultaneous Formation of a Fully Organic Triply Dynamic Combinatorial Library

Drożdż, Wojciech; Walczak, Anna; Stefankiewicz, Artur R.

doi:10.1021/acs.orglett.1c01042

Cited by 9 publications

(5 citation statements)

References 24 publications

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“…, chemo-selectively) and simultaneously. Several reversible covalent reactions have been reported to operate by combination of two (imine/olefin metathesis, 117 imine/boronic ester, 20,107,118,119 B–N and B–O bonds within amidoboronates 120 ), three (disulphide/hydrazone/boronic 121,122 and disulphide/imine/boronic 123 ), and even four coupling reactions (thiol addition/hydrazone/boronic ester/coordination 124 ).…”

Section: Syntheses Based On Multiple Reversible Covalent Reactionsmentioning

confidence: 99%

Dynamic covalent synthesis

Cougnon,

Stefankiewicz,

Ulrich

2024

Chem. Sci.

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Section: Syntheses Based On Multiple Reversible Covalent Reactionsmentioning

confidence: 99%

Dynamic covalent synthesis

Cougnon,

Stefankiewicz,

Ulrich

2024

Chem. Sci.

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“…One of the challenges of modern DCC is to expand the chemical diversity within libraries in terms of reactive moieties devoted either to covalent binding (building block to building block) or to noncovalent binding (building block to template). To expand the scope of covalent binding simultaneously at work within a single DCL, both orthogonal (i.e., involving different reactive moieties) − and competing (i.e., sharing at least one reactive moiety) DCRs were combined . As covalent bonds are considered significantly more energetic than noncovalent interactions, the templating approach has only been applied so far to displace isoenergetic covalent reactions such as substitution or metathesis processes. , To the best of our knowledge, favoring one reversible covalent chemistry at the expense of another by a templating approach has never been reported to date.…”

Section: Introductionmentioning

confidence: 99%

Switching between Nonisoenergetic Dynamic Covalent Reactions Using Host–Guest Chemistry

Chetot,

Marocco Stuardi,

Forot

et al. 2024

J. Am. Chem. Soc.

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CO 2 reacts with simple amines in the presence of water to generate dynamic combinatorial libraries of majority (i.e., ammonium carbamates) and minority (i.e., ammonium carbonates) nonisoenergetic covalent adducts. Over the past two decades, our laboratory has reported on a new class of cavitands, namely, dyn[n]arenes, from which a polyanionic macrocycle is a highly efficient receptor for linear polyammoniums that forms [2]pseudorotaxanes in water at neutral pH. Herein, we demonstrate that the formation of [2]pseudorotaxanes shifts the equilibrium of CO 2 capture by polyamines in water toward the quasi-exclusive formation of carbonate adducts, providing the first example of a switch between two competitive and reversible covalent processes triggered by host−guest interactions. In addition, this supramolecular approach to CO 2 capture exhibits enhanced capture efficiency by increasing the state of protonation of complexed vs uncomplexed polyamines. Altogether, we report here that a templating approach can divert the outcome of two reversible covalent chemistries involving nucleophilic additions and acid−base reactions, challenging therefore the common knowledge that noncovalent and covalent bonds operate in separate energy frames.

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“…However, incorporation of two or more dynamic reactions allows to increase complexity, because more than one dynamic library is generated. Most of the reported examples of multi‐reaction dynamic systems consist of orthogonal reversible reactions, [17–42] in which the same functional group does not participate in two different reversible chemistries. Then, dynamic libraries obtained are not interconnected, or in other words, a building block from one library cannot participate in the other.…”

Section: Introductionmentioning

confidence: 99%

Kinetic Control of Complexity in Multiple Dynamic Libraries

Rivero,

Pérez‐Pérez,

Perretti

et al. 2024

Angewandte Chemie

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Multiple dynamic libraries of compounds are generated when more than one reversible reaction comes into play. Commonly, two or more orthogonal reversible reactions are used, leading to non‐communicating dynamic libraries which share no building blocks. Only a few examples of communicating libraries have been reported, and in all those cases, building blocks are reversibly exchanged from one library to the other, constituting an antiparallel dynamic covalent system. Herein we report that communication between two different dynamic libraries through an irreversible process is also possible. Indeed, alkyl amines cancel the dynamic regime on the nucleophilic substitution of tetrazines, generating kinetically inert compounds. Interestingly, such amine can be part of another dynamic library, an imine‐amine exchange. Thus, both libraries are interconnected with each other by an irreversible process which leads to kinetically inert structures that contain parts from both libraries, causing a collapse of the complexity. Additionally, a latent irreversible intercommunication could be developed. In such a way, a stable molecular system with specific host‐guest and fluorescence properties, could be irreversibly transformed when the right stimulus was applied, triggering the cancellation of the original supramolecular and luminescent properties and the emergence of new ones.

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Simultaneous Formation of a Fully Organic Triply Dynamic Combinatorial Library

Cited by 9 publications

References 24 publications

Dynamic covalent synthesis

Dynamic covalent synthesis

Switching between Nonisoenergetic Dynamic Covalent Reactions Using Host–Guest Chemistry

Kinetic Control of Complexity in Multiple Dynamic Libraries

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