Control over Unfolding Pathways by Localizing Photoisomerization Events within Heterosequence Oligoazobenzene Foldamers

Yu, Zhilin; Hecht, Stefan

doi:10.1002/anie.201307378

Cited by 45 publications

(81 citation statements)

References 44 publications

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“…Die Azobenzoleinheit nimmt dabei eine herausragende Rolle ein, da sie mittels Licht zwischen E-u nd Z-Isomer geschaltet werden kann. [17] Des Weiteren wurden Arbeiten über die Integration in Foldamere [18] und Polymere [19] publiziert. [15] Das zunehmende Interesse hat zu einem starken Anstieg von Publikationen geführt, in welchen die Effekte von verschiedenen Substituenten auf die Isomerisierung vom thermodynamisch instabilen Z-z um stabilen E-Isomer untersucht wurden.…”

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Anziehung oder Abstoßung? London‐Dispersionswechselwirkungen kontrollieren Azobenzol‐basierte molekulare Schalter

et al. 2015

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Aufgrund sterischer Hinderung wird großen Substituenten im Allgemeinen eine rein abstoßende Wirkung zugesprochen. Solche Reste haben jedocha ucha nziehende Eigenschaften, die durch schwache London-Dispersionskräfte zwischen den neutralen Atomen hervorgerufen werden. In Lehrbüchern wird sterische Hinderung häufig als Grund für die Destabilisierung des Z-isomers genannt, z. B. bei Isomerisierungen wie bei Azobenzol-basierten molekularen Schaltern. Hier zeigen wir,d ass eine Vergrçßerung der Substituenten in der meta-Position des Azobenzols, unter Beibehaltung der elektronischen Struktur der Reste,d ie thermischeZ -zu-E-Isomerisierung verlangsamt. DFT-Rechnungen untermauern, dass die Energie des Z-Isomers durch anziehende Dispersionswechselwirkungen deutlichg esenkt wird.

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Anziehung oder Abstoßung? London‐Dispersionswechselwirkungen kontrollieren Azobenzol‐basierte molekulare Schalter

et al. 2015

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“…[ 6 ] Then, Hecht et al introduced a photoisomerizable unit in the molecular backbone to accurately control the formation of the fi nal foldamers. [ 7 ] For the synergistic assemblies, van Esch et al recently discovered a fuel-driven self-assembly process, in which reaction rates and fuel levels, instead of equilibrium composition, determine the properties of the resulted assembly. [ 8 ] Otto and co-workers accurately analyzed the process of self-replicated molecules.…”

Section: Discussionmentioning

confidence: 99%

Synergistic Assembly of Covalent and Supramolecular Polymers

Bai

Zhao

2016

Macromol. Rapid Commun.

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Integrating irreplaceable features of both covalent chemistry and noncovalent interactions into a single entity to maximize the applicability is highly desired. Here, a discovery of this type of hybrid, developed by Stupp and co-workers, is developed, where a synergistic combination of covalent and noncovalent compartments enables them to assemble by each other perfectively. The covalent compartments can grow into polymer chains assisted by a supramolecular compartment. The supramolecular compartments can be reversibly removed and re-formed to reconstitute the hybrid structure. The obtained soft materials can serve as functional platforms for molecular delivery or self-repairing materials.

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“…These artificial foldamers can not only serve as protein–protein interaction mediators and molecular receptors like biopolymers, but also exhibit great potential in molecular materials, such as molecular containers and tubes, sensors, molecular shuttles and machines, and so on. However, although numerous artificial foldamers have been reported, with confines ranging from flexible to rigid, folded types forming a secondary folded motif are still comparatively rare . While most foldamers adopt a secondary structure in helices, other types of folding, such as parallel folding of the chemical units, are very rare .…”

Section: Introductionmentioning

confidence: 99%

Tetraphenylethylene Foldamers with Double Hairpin‐Turn Linkers, TNT‐Binding Mode and Detection of Highly Diluted TNT Vapor

Xiong

Feng

Wang

et al. 2018

Chemistry A European J

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Tetraphenylethylene (TPE) foldamers with double hairpin-turn linkers showing an aggregation-induced emission (AIE) effect have been synthesized for the first time. A crystal structure of a foldamer-TNT complex has been obtained, enabling unprecedented direct observation of the interactions between TNT molecules and the chromophores of the foldamer. Instead of π-π stacking interactions, which have often been considered to be the key mechanism in the binding of TNT by chromophoric receptors, strong n-π interactions between the nitro groups of TNT and the aromatic rings of the foldamer have been found. Exceptionally, by addition of 1 % NaF to a suspension of the foldamer in H O/THF (95:5), the fluorescence quenching efficiency by TNT vapor significantly increased from about 20 % to more than 90 %. Even after diluting TNT-saturated air at 25 °C by a factor of 2×10 , an obvious quenching response was observed, indicating that ultratrace TNT vapor (down to 3.4 fg per mL of air) could be detected.

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Control over Unfolding Pathways by Localizing Photoisomerization Events within Heterosequence Oligoazobenzene Foldamers

Cited by 45 publications

References 44 publications

Anziehung oder Abstoßung? London‐Dispersionswechselwirkungen kontrollieren Azobenzol‐basierte molekulare Schalter

Anziehung oder Abstoßung? London‐Dispersionswechselwirkungen kontrollieren Azobenzol‐basierte molekulare Schalter

Synergistic Assembly of Covalent and Supramolecular Polymers

Tetraphenylethylene Foldamers with Double Hairpin‐Turn Linkers, TNT‐Binding Mode and Detection of Highly Diluted TNT Vapor

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