Controlling monomer-sequence using supramolecular templates

Brummelhuis, Niels ten

doi:10.1039/c4py01522c

Cited by 82 publications

(60 citation statements)

References 96 publications

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“…Directly inspired by biologically accessible DNA systems—for example, nucleobase-coded chains—sequence-defined macromolecules have been synthesized employing template-based coding strategies26272829 or via the generation of regulated sequence alternating thymine hybrid polymers30, as well as the design of reactions with iterative protection/deprotection steps on supports3132. Further, bulk reactions have been conducted in flow systems based on iterative synthesis33.…”

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Coding and decoding libraries of sequence-defined functional copolymers synthesized via photoligation

et al. 2016

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Designing artificial macromolecules with absolute sequence order represents a considerable challenge. Here we report an advanced light-induced avenue to monodisperse sequence-defined functional linear macromolecules up to decamers via a unique photochemical approach. The versatility of the synthetic strategy—combining sequential and modular concepts—enables the synthesis of perfect macromolecules varying in chemical constitution and topology. Specific functions are placed at arbitrary positions along the chain via the successive addition of monomer units and blocks, leading to a library of functional homopolymers, alternating copolymers and block copolymers. The in-depth characterization of each sequence-defined chain confirms the precision nature of the macromolecules. Decoding of the functional information contained in the molecular structure is achieved via tandem mass spectrometry without recourse to their synthetic history, showing that the sequence information can be read. We submit that the presented photochemical strategy is a viable and advanced concept for coding individual monomer units along a macromolecular chain.

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Coding and decoding libraries of sequence-defined functional copolymers synthesized via photoligation

et al. 2016

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“…On the other hand, some approaches take advantage of automated systems . In this section, synthesis procedures towards non‐conjugated and conjugated sequence‐defined macromolecules are described, but (DNA)‐templated approaches were omitted since they were described in a recent review by Ten Brummelhuis and are not scalable for applications in polymer science …”

Section: Liquid‐phase Synthesis Of Sequence‐defined Macromoleculesmentioning

confidence: 99%

Recent Progress in the Design of Monodisperse, Sequence-Defined Macromolecules

Solleder

Schneider

Wetzel

et al. 2017

Macromol. Rapid Commun.

181

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This review describes different synthetic strategies towards sequence-defined, monodisperse macromolecules, which are built up by iterative approaches and lead to linear non-natural polymer structures. The review is divided in three parts: solution phase-, solid phase-, and fluorous- and polymer-tethered approaches. Moreover, synthesis procedures leading to conjugated and non-conjugated macromolecules are considered and discussed in the respective sections. A major focus in the evaluation is the applicability of the different approaches in polymer chemistry. In this context, simple procedures for monomer and oligomer synthesis, overall yields, scalability, purity of the oligomers, and the achievable level of control (side-chains, backbone, stereochemistry) are important benchmarks.

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“…Current strategies to generate sequence‐controlled macromolecules rely on the sequential addition of monomers or solid‐phase syntheses . These strategies are perfect for the generation of well‐defined model compounds on small scale (typically several hundred milligrams); however, they are not suitable for large‐scale production and cannot be combined with established techniques.…”

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Sequence-Controlled Polymers via Simultaneous Living Anionic Copolymerization of Competing Monomers

Rieger

Alkan

Manhart

et al. 2016

Macromol. Rapid Commun.

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Natural macromolecules, i.e., sequence-controlled polymers, build the basis for life. In synthetic macromolecular chemistry, reliable tools for the formation of sequence-controlled macromolecules are rare. A robust and efficient chain-growth approach based on the simultaneous living anionic polymerization of sulfonamide-activated aziridines for sequence control of up to five competing monomers resulting in gradient copolymers is presented. The simultaneous azaanionic copolymerization is monitored by real-time (1) H NMR spectroscopy for each monomer at any time during the reaction. The monomer sequence can be adjusted by the monomer reactivity, depending on the electron-withdrawing effect by the sulfonamide (nosyl-, brosyl-, tosyl-, mesyl-, busyl) groups. This method offers unique opportunities for sequence control by competing copolymerization: a step forward to well-engineered synthetic polymers with defined microstructures.

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Controlling monomer-sequence using supramolecular templates

Abstract: This review discusses the template-directed preparation of sequence-defined polymers.

Cited by 82 publications

References 96 publications

Coding and decoding libraries of sequence-defined functional copolymers synthesized via photoligation

Coding and decoding libraries of sequence-defined functional copolymers synthesized via photoligation

Recent Progress in the Design of Monodisperse, Sequence-Defined Macromolecules

Sequence-Controlled Polymers via Simultaneous Living Anionic Copolymerization of Competing Monomers

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