Generation of a Multicomponent Library of Disulfide Donor-Acceptor Architectures Using Dynamic Combinatorial Chemistry.

Wojciech Drożdż,Michał Kołodziejski,Grzegorz Markiewicz,Anna Jenczak,Artur Stefankiewicz

doi:10.3390/ijms160716300

Wojciech Drożdż, Michał Kołodziejski + Show 3 more

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https://doi.org/10.3390/ijms160716300

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Abstract

We describe here the generation of new donor-acceptor disulfide architectures obtained in aqueous solution at physiological pH. The application of a dynamic combinatorial chemistry approach allowed us to generate a large number of new disulfide macrocyclic architectures together with a new type of [2]catenanes consisting of four distinct components. Up to fifteen types of structurally-distinct dynamic architectures have been generated through one-pot disulfide exchange reactions between four thiol-functionalized aqueous components. The distribution of disulfide products formed was found to be strongly dependent on the structural features of the thiol components employed. This work not only constitutes a success in the synthesis of topologically- and morphologically-complex targets, but it may also open new horizons for the use of this methodology in the construction of molecular machines.

Highlights

The emerging area of molecular and supramolecular multi-component synthesis is very promising, since it becomes possible to incorporate multiple molecular building blocks in combination with multiple covalent and/or noncovalent bonds to create functional architectures with applications in, for example, recognition, sensing, catalysis, transport and encapsulation [1,2]
We have extended the disulfide donor–acceptor dynamic combinatorial chemistry (DCC) chemistry by introduction of a new type of thiol-functionalized building block
This viologen-based electron-deficient structure was found to be very effective in promoting the formation of a series of new D–A disulfide architectures, including [2]catenanes

Summary

Introduction

The emerging area of molecular and supramolecular multi-component synthesis is very promising, since it becomes possible to incorporate multiple molecular building blocks in combination with multiple covalent and/or noncovalent bonds to create functional architectures with applications in, for example, recognition, sensing, catalysis, transport and encapsulation [1,2]. Despite the remarkable success of dynamic combinatorial and supramolecular chemistries, the construction of dynamic multi-component architectures or devices with interesting morphological and structural features is still challenging [3]. The development of dynamic multi-component assemblies generated through the formation of reversible covalent or noncovalent bonds is at the forefront of recent research on supramolecular chemistry, with the ultimate goals of creating molecular machines, complex functional nanoarchitectures, dynamic combinatorial libraries and sensors [9,10,11,12]. Reversible bonding (covalent and noncovalent) [13,14,15,16] is often employed for the creation of such novel molecular and supramolecular structures, multi-component assemblies and sensing ensembles [17,18,19]. The main stream of investigation is directed towards finding quick and efficient ways to control and reversibly modify the composition of molecular or supramolecular architectures [20]

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