Chemical Science, Journal Year: 2022, Volume and Issue: 13(39), P. 11551 - 11559
Published: Jan. 1, 2022
The synthesis of red-shifted azobenzenes functionalised with heavy chalcogen and halogen substituents is reported, enabling photo-switching red near IR light Z → E thermal isomerization rates spanning seven orders magnitude.
Language: Английский
ACS Chemical Biology, Journal Year: 2021, Volume and Issue: 17(12), P. 3255 - 3269
Published: Sept. 13, 2021
The complex network of naturally occurring biological pathways motivates the development new synthetic molecules to perturb and/or detect these processes for fundamental research and clinical applications. In this context, photochemical tools have emerged as an approach control activity drug or probe at high temporal spatial resolutions. Traditional tools, particularly photolabile protecting groups (photocages) photoswitches, rely on high-energy UV light that is only applicable cells transparent model animals. More recently, such designs evolved into visible near-infrared regions with deeper tissue penetration, enabling photocontrol study biology in animal contexts. This Review highlights recent developments far-red photocages photoswitches their current potential applications interface chemistry biology.
Language: Английский
Citations
60
Natural Sciences, Journal Year: 2022, Volume and Issue: 3(1)
Published: Nov. 8, 2022
Abstract Photocontrol of functional molecules and supramolecular systems provides promising directions for the development innovative materials technologies. Reversible photoswitches that can isomerize among different states play a vital role in such photoresponsive systems. However, commonly used UV light triggering isomerization as azobenzene (AB) has limited their applications material because penetrates poorly causes damage to or biological tissues. Accordingly, tremendous endeavors have been devoted visible‐light‐switchable expand new various fields. Herein, we highlight strategies molecule design ABs by discussing effects benzene substituents on absorption spectrum. Based this, visible‐light‐responsive with metal–organic frames, cyclodextrins, nanoparticles, biomolecules (DNAs, peptides, proteins) are elaborated. Then, light‐responsive mechanical properties emerging actuators, systems, information storage, energy nonlinear optical devices, photoswitchable adhesives discussed. Finally, summary challenges perspective outlined. Key points Structural azobenzenes Visible‐light‐responsive research areas ranging from chemistry biology Their
Language: Английский
Citations
58
Chinese Chemical Letters, Journal Year: 2021, Volume and Issue: 32(8), P. 2359 - 2368
Published: March 10, 2021
Language: Английский
Citations
57
Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 62(8)
Published: Dec. 13, 2022
A series of macrocyclic azobenzene-based chiral photoswitches have been judiciously designed, synthesized, and characterized. In the molecular structures, binaphthyl is covalently linked to ortho-positions azobenzene, four different substituents are 6,6'-positions binaphthyl. The show enhanced helical twisting power (HTP) when doping in commercially available achiral liquid crystals form self-organized superstructures, i.e., cholesteric (CLCs). All exhibit reversible photoisomerization driven by visible light wavelengths both organic solvent crystals. with shorter enable handedness inversion CLCs upon photoisomerization. These first examples ortho-linked that CLCs. longer display only HTP values decreasing while maintaining same handedness.
Language: Английский
Citations
52
Photochemical & Photobiological Sciences, Journal Year: 2022, Volume and Issue: 21(10), P. 1719 - 1734
Published: July 27, 2022
Azobenzenes have many faces. They are well-known as dyes, but most of all, azobenzenes versatile photoswitchable molecules with powerful photochemical properties. Azobenzene photochemistry has been extensively studied for decades, only relatively recently research taken a steer towards applications, ranging from photonics and robotics to photobiology. In this perspective, after an overview the recent trends in molecular design azobenzenes, we highlight three areas where azobenzene photoswitches may bring about promising technological innovations: chemical sensing, organic transistors, cell signaling. Ingenious designs enabled control properties, which turn facilitated development sensors transistors. Finally, power biology is exemplified by vision restoration photactivation neural Although selected examples reveal some faces expect fields presented develop rapidly near future, that will play central role development.
Language: Английский
Citations
42
ACS Applied Optical Materials, Journal Year: 2023, Volume and Issue: 1(2), P. 633 - 639
Published: Feb. 13, 2023
Photomelting of azobenzene is a phenomenon that typically achieved by UV-light irradiation. However, many applications based on photomelting, including the solar thermal fuel (STF) application, require responsiveness to visible light. Therefore, in this study, we designed and synthesized several derivatives melt under visible-light irradiation explored their potential application as STFs. By combining molecular design elements endow with visible-light-responsiveness (ortho-halogen) photomeltability (para-alkoxy), successfully four compounds exhibit photomelting properties. These also long cis-isomer lifetime, which makes them good candidates for STFs future.
Language: Английский
Citations
24
Polymer Journal, Journal Year: 2024, Volume and Issue: unknown
Published: Jan. 16, 2024
Abstract Photoinduced transitions between the solid, glass, and liquid states based on molecular photoswitches promise a wide variety of applications. Photoswitchable adhesives are representative examples expected to contribute material recycling for sustainable future in era composite materials due strong bonding on-demand photo-induced debonding with minimal damage adherends. Only few known undergo these transitions, but recent progress, mainly azobenzene, has been remarkable. Here, we review photoinduced small molecules polymers over approximately decade systematically discuss designs, mechanisms, applications, merits demerits, challenges each photoswitch whole field. We hope this provides useful information, inspiration, ideas development field expansion its
Language: Английский
Citations
12
Angewandte Chemie International Edition, Journal Year: 2021, Volume and Issue: 60(44), P. 23695 - 23704
Published: Aug. 30, 2021
We report the first cellular application of emerging near-quantitative photoswitch pyrrole hemithioindigo, by rationally designing photopharmaceutical PHTub inhibitors cytoskeletal protein tubulin. PHTubs allow simultaneous visible-light imaging and photoswitching in live cells, delivering cell-precise photomodulation microtubule dynamics, photocontrol over cell cycle progression death. This is acute use a hemithioindigo for high-spatiotemporal-resolution biological control cells. It additionally demonstrates utility photoswitches, enabling dark-active design to overcome residual background activity during photopatterning. work opens up new horizons high-precision research using shows applicability as valuable scaffold range other targets.
Language: Английский
Citations
56
Chemistry - A European Journal, Journal Year: 2021, Volume and Issue: 27(31), P. 8094 - 8099
Published: March 26, 2021
Molecular photoswitches triggered with red or NIR light are optimal for photomodulation of complex biological systems, including efficient penetration the human body therapeutic purposes ("therapeutic window"). Yet, they rarely reported, and even more functional under aqueous conditions. In this work, fluorinated azobenzenes shown to exhibit E→Z photoisomerization (PSS660nm >75 % Z) upon conjugation unsaturated substituents. Initially demonstrated aldehyde groups, effect was also observed in a structure by incorporating chromophore into cyclic dipeptide propensity self-assembly. Under physiological conditions, latter molecule formed supramolecular material that reversibly changed its viscosity irradiation light. Our observation can lead design new photopharmacology agents phototriggered materials vivo use.
Language: Английский
Citations
54
Journal of the American Chemical Society, Journal Year: 2020, Volume and Issue: 142(47), P. 19969 - 19979
Published: Nov. 12, 2020
We report a series of azobenzene boronic acids that reversibly control the extent diol binding via photochemical isomerization. When acid is ortho to azo group, thermodynamically favored E isomer binds weakly with diols form esters. The isomerization (E)-azobenzene its Z enhances binding, and magnitude this enhancement affected by structure. 2,6-Dimethoxy show an over 20-fold in upon → isomerization, which can be triggered red light. Competition experiments computational studies suggest changes affinity originate from stabilization (E)-boronic destabilization demonstrate correlation between photostationary state, such different wavelengths irradiation yield quantities bound diol. Higher constants for relative were observed all investigated, including cyclic diols, nitrocatechol, biologically relevant compounds, polyols. This photoswitch was employed "catch release" fluorophore-tagged buffered water. By tethering poly(ethylene glycol) star polymer, we tune stiffness covalent adaptable hydrogels using visible paper describes how structural modifications azobenzenes influence isomerism-dependent thermodynamics their dynamic bonds small molecules macromolecules.
Language: Английский
Citations
53