Controlling forward and backward rotary molecular motion on demand DOI Creative Commons
Lukas Pfeifer, Stefano Crespi,

Pieter van der Meulen

et al.

Nature Communications, Journal Year: 2022, Volume and Issue: 13(1)

Published: April 19, 2022

Abstract Synthetic molecular machines hold tremendous potential to revolutionize chemical and materials sciences. Their autonomous motion controlled by external stimuli allows develop smart whose properties can be adapted on command. For the realisation of more complex machines, it is crucial design building blocks multiple orthogonal stimuli. A major challenge reversibly switch from forward backward again light-driven rotary using Here we report a push-pull substituted photo-responsive overcrowded alkene function toggled between that unidirectional 2 nd generation motor depending its protonation polarity environment. With simplicity in design, easy preparation, outstanding stability control distinct motions, believe present concept paves way for creating advanced machines.

Language: Английский

Molecular photoswitches in aqueous environments DOI Creative Commons
Jana Volarić, Wiktor Szymański, Nadja A. Simeth

et al.

Chemical Society Reviews, Journal Year: 2021, Volume and Issue: 50(22), P. 12377 - 12449

Published: Jan. 1, 2021

Molecular photoswitches are inherently lipophilic and do not spontaneously dissolve in water. We describe the effect of water on photochemical properties strategies to solubilize organic apply them aqueous media.

Language: Английский

Citations

282

Photoresponsive molecular tools for emerging applications of light in medicine DOI Creative Commons
Ilse M. Welleman, Mark W. H. Hoorens, Ben L. Feringa

et al.

Chemical Science, Journal Year: 2020, Volume and Issue: 11(43), P. 11672 - 11691

Published: Jan. 1, 2020

This perspective article explores the current state of light-controlled molecular tools for medical therapy and imaging offers an outlook on clinical application scenarios optimisation strategies.

Language: Английский

Citations

197

Photoresponsive Supramolecular Polymers: From Light‐Controlled Small Molecules to Smart Materials DOI Creative Commons
Fan Xu, Ben L. Feringa

Advanced Materials, Journal Year: 2022, Volume and Issue: 35(10)

Published: Oct. 14, 2022

Photoresponsive supramolecular polymers are well-organized assemblies based on highly oriented and reversible noncovalent interactions containing photosensitive molecules as (co-)monomers. They have attracted increasing interest in smart materials dynamic systems with precisely controllable functions, such light-driven soft actuators, photoresponsive fluorescent anticounterfeiting light-triggered electronic devices. The present review discusses light-activated used their main photo-induced changes, e.g., geometry, dipole moment, chirality. Based these distinct formed by exhibit disassembly reassembly. As a consequence, polymerization, "depolymerization," regulation of the lengths topologies observed. Moreover, light-controlled functions polymers, actuation, emission, chirality transfer along length scales, highlighted. Furthermore, perspective challenges future opportunities is presented. Besides challenge moving from harmful UV light to visible/near IR avoiding fatigue, enabling biomedical applications, include actuators helical motion, light-modulated information transmission, optically recyclable materials, multi-stimuli-responsive systems.

Language: Английский

Citations

157

Stiff‐Stilbene Photoswitches: From Fundamental Studies to Emergent Applications DOI Creative Commons
David Villarón, Sander J. Wezenberg

Angewandte Chemie International Edition, Journal Year: 2020, Volume and Issue: 59(32), P. 13192 - 13202

Published: March 28, 2020

Abstract Stiff‐stilbene, a sterically restricted fused ring analogue of stilbene, has been regularly used as model compound in theoretical studies stilbene photoisomerization. Lately, owing to its excellent photoswitching properties, it is increasingly being applied reversibly control the properties and function chemical well biological systems. Stiff‐stilbene photoswitches possess number advantageous including high quantum yield for photoisomerization thermal stability. Furthermore, they undergo large geometrical change upon isomerization their synthesis straightforward. Herein, we provide an overview basic stiff‐stilbene recent applications supramolecular chemistry, catalysis,

Language: Английский

Citations

156

Storing energy with molecular photoisomers DOI Creative Commons
Zhihang Wang, Paul Erhart, Tao Li

et al.

Joule, Journal Year: 2021, Volume and Issue: 5(12), P. 3116 - 3136

Published: Nov. 22, 2021

Some molecular photoisomers can be isomerized to a metastable high-energy state by exposure light. These molecules then thermally or catalytically converted back their initial state, releasing heat in the process. Such reversible photochemical process has been considered for developing solar thermal (MOST) systems. In this review, we introduce concept, criteria, and state-of-the-art of MOST systems, with an emphasis on three most promising systems: norbornadiene/quadricyclane, E/Z-azobenzene, dihydroazulene/vinylheptafulvene. After discussing fundamental working principles, focus design strategies improving energy storage performance, remaining challenges, potential areas. Finally, summarize current incorporation into functional devices conclude perspective challenges future directions.

Language: Английский

Citations

152

Stimulus-Controlled Anion Binding and Transport by Synthetic Receptors DOI Creative Commons
Jorn de Jong, Jasper E. Bos, Sander J. Wezenberg

et al.

Chemical Reviews, Journal Year: 2023, Volume and Issue: 123(13), P. 8530 - 8574

Published: June 21, 2023

Anionic species are omnipresent and involved in many important biological processes. A large number of artificial anion receptors has therefore been developed. Some these capable mediating transmembrane transport. However, where transport proteins can respond to stimuli their surroundings, creation synthetic with stimuli-responsive functions poses a major challenge. Herein, we give full overview the stimulus-controlled that have developed thus far, including application membrane In addition potential operation as carriers, use recognition motifs forming responsive membrane-spanning channels is discussed. With this review article, intend increase interest among scientists working on host–guest complexes dynamic functional systems order stimulate further developments.

Language: Английский

Citations

44

Photoswitchable imines: aryliminopyrazoles quantitatively convert to long-lived Z-isomers with visible light DOI Creative Commons
Jiarong Wu, Lasse Kreimendahl,

Suyuan Tao

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(11), P. 3872 - 3878

Published: Jan. 1, 2024

Simple structural modifications significantly boost the photochromic performance of imine-based photoswitches. This work lays a foundation for exploring new motifs in light-addressable dynamic combinatorial chemistry.

Language: Английский

Citations

18

Rhodanine-Based Chromophores: Fast Access to Capable Photoswitches and Application in Light-Induced Apoptosis DOI

Laura Köttner,

Friederike Wolff,

P. Mayer

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(3), P. 1894 - 1903

Published: Jan. 11, 2024

Molecular photoswitches are highly desirable in all chemistry-related areas of research. They provide effective outside control over geometric and electronic changes at the nanoscale using an easy to apply, waste-free stimulus. However, simple access such molecular tools is typically not granted, elaborate syntheses substitution schemes needed order obtain efficient photoswitching properties. Here we present a series rhodanine-based that can be prepared one synthetic step without requiring purification. Photoswitching induced by UV visible light both switching directions, thermal stabilities metastable states as well quantum yields very high. An additional benefit hydrogen-bonding capacity rhodanine fragment, which enables applications supramolecular or medicinal chemistry. We further show known inhibitor SMI-16a photoswitchable apoptosis inducer. The biological activity effectively switched ON OFF reversible photoisomerization between inactive E active Z isomer. Rhodanine-based therefore represent valuable toolbox for implementing responsiveness breadth functional systems.

Language: Английский

Citations

17

More Than Resveratrol: New Insights into Stilbene-Based Compounds DOI Creative Commons
Paulina Pecyna,

Joanna Warguła,

Marek Murias

et al.

Biomolecules, Journal Year: 2020, Volume and Issue: 10(8), P. 1111 - 1111

Published: July 27, 2020

The concept of a scaffold concerns many aspects at different steps on the drug development path. In medicinal chemistry, choice relevant “drug-likeness” is starting point for design structure dedicated to specific molecular targets. For years, chemical uniqueness stilbene has inspired scientists from fields such as biology, pharmacy, and medicine. this review, we present outstanding potential stilbene-based derivatives. Naturally occurring stilbenes, together with powerful synthetic chemistry possibilities, may offer an excellent approach discovering new structures identifying their therapeutic With scientific tools, sophisticated equipment, better understanding disease pathogenesis level, moved innovation in science. This paper mainly focuses compounds beyond resveratrol, which are particularly attractive due biological activity. Given “fresh outlook” about stilbenoids particular regard isorhapontigenin methoxy- hydroxyl- analogues, update combretastatins, very often overlooked underestimated benzanilide story remarkable structure.

Language: Английский

Citations

117

General Principles for the Design of Visible‐Light‐Responsive Photoswitches: Tetra‐ortho‐Chloro‐Azobenzenes DOI Creative Commons
Lucien N. Lameijer, Šimon Budzák, Nadja A. Simeth

et al.

Angewandte Chemie International Edition, Journal Year: 2020, Volume and Issue: 59(48), P. 21663 - 21670

Published: Aug. 28, 2020

Molecular photoswitches enable reversible external control of biological systems, nanomachines, and smart materials. Their development is driven by the need for low energy (green-red-NIR) light switching, to allow non-invasive operation with deep tissue penetration. The lack clear design principles adaptation optimization such systems limits further applications. Here we provide a rulebook tetra-ortho-chloroazobenzenes, an emerging class visible-light-responsive photochromes, elucidating role that substituents play in defining their key characteristics: absorption spectra, band overlap, photoswitching efficiencies, half-lives unstable cis isomers. This achieved through joint photochemical theoretical analyses representative library molecules featuring varying electronic nature. A set guidelines presented enables tuning properties desired application informed photochrome engineering.

Language: Английский

Citations

117