Photocontrolled chiral supramolecular assembly of azobenzene amphiphiles in aqueous media

Cheung, Leong-Hung; Liu, B.; Leung, Franco King‐Chi

doi:10.1038/s41428-023-00792-7

Cited by 6 publications

(3 citation statements)

References 62 publications

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“…These photoresponsive molecular amphiphilic systems can assemble at the microscopic length-scale and respond to multiple stimulations; however, assembling multiple stimulation-controlled photoresponsive molecular amphiphiles across multiple length-scales for fabricating macroscopic materials remains challenging. Pioneered by Leung and Feringa, a series of supramolecular soft actuators were prepared from molecular motor amphiphiles as macroscopic materials and even showed excellent cytocompatibility. ,− Later, we reported a series of macroscopic soft scaffolds of photoresponsive molecular amphiphiles, including stiff-stilbene amphiphiles, donor–acceptor Stenhouse adduct amphiphiles, indigo amphiphiles, and azobenzene amphiphiles. − These macroscopic soft scaffolds, instead of photoactuation, perform material contraction, shape disintegration, and color fading for potential smart functional applications, e . g ., photocontrolled target release.…”

Section: Introductionmentioning

confidence: 99%

Tailoring Multicontrolled Supramolecular Assemblies of Stiff-Stilbene Amphiphiles into Macroscopic Soft Scaffolds as Cell-Material Interfaces

Cheung,

To,

Wong

et al. 2024

ACS Appl. Mater. Interfaces

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Biocompatible synthetic supramolecular systems have shed light on biomedical and tissue-regenerative material applications. The intrinsic functional applicability, tunability, and stimuli-responsiveness of synthetic supramolecular systems allow one to develop various multicontrolled supramolecular assemblies in aqueous media. However, it remains highly challenging to use state-of-the-art supramolecular assemblies of photoresponsive amphiphiles controlled by multiple stimulations in fabricating macroscopic materials. Herein, we demonstrate a stiff-stilbene amphiphile (SA) multicontrolled supramolecular assembling system that comprises two different charged end groups. The excellent photoswitchabilities of SA in both organic and aqueous media are demonstrated. Furthermore, multiple stimuli, i.e., light, pH, and counterions, are applied to control the supramolecular assembling behaviors, which are monitored by circular dichroism spectroscopy and electron microscopies. This multicontrolled supramolecular system can be systematically assembled into macroscopic soft functional scaffolds, whose structural parameters are investigated by electron microscopies and X-ray diffraction techniques, suggesting the large aspect ratio of SA nanostructures assembled into macroscopic soft scaffolds. The fabricated soft functional scaffold is highly biocompatible for photocontrolled biotarget encapsulation/release selectively, as well as a cell-material interface for diverse cells' attachment. This new synthetic multicontrolled soft functional material provides a new strategy toward the development of next-generation controllable and biocompatible soft functional materials.

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Section: Introductionmentioning

confidence: 99%

Tailoring Multicontrolled Supramolecular Assemblies of Stiff-Stilbene Amphiphiles into Macroscopic Soft Scaffolds as Cell-Material Interfaces

Cheung,

To,

Wong

et al. 2024

ACS Appl. Mater. Interfaces

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“…In particular, photoswitchable moieties provide fascinating possibilities. Photoisomerization of azo compounds has been used to change the affinity to metal ions, the binding to organic molecules, for example, in host–guest chemistry , or in biological applications, to modulate catalysis and for reversible assembly of nanostructures. , Magnetic NP have been functionalized with azobenzene and its derivatives, leading to hybrid nanomaterials that can be manipulated both magnetically and by light. These examples are mainly studied in organic solvents because of the low polarity of azo compounds and therefore low solubility in aqueous media. − However, water-dispersible, photoresponsive MNP are advantageous for biomedical applications in photopharmacology or drug delivery.…”

Section: Introductionmentioning

confidence: 99%

Multi-Stimuli-Responsive Water-Dispersible Magnetite Nanoparticles Using Arylazopyrazole-Modified Polymer Ligands

Schlichter,

Jersch,

Demokritov

et al. 2024

Langmuir

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“…Light enables noninvasive stimulation with high spatial and temporal precision to control structural transformations of supramolecular assemblies in organic and aqueous media [ 19 , 23 – 25 ]. Various photochromic and photoresponsive moieties, such as, stiff-stilbene [ 26 ], azobenzene [ 27 – 28 ], molecular motors [ 19 , 29 – 30 ], spiropyran [ 31 – 33 ], indigo [ 34 – 35 ], and donor–acceptor Stenhouse adducts (DASAs) [ 36 – 37 ], have been used in supramolecular systems for photoswitchable smart electronic, optoelectronic, and biomedical materials [ 30 , 38 – 40 ].…”

Section: Introductionmentioning

confidence: 99%

Supramolecular assemblies of amphiphilic donor–acceptor Stenhouse adducts as macroscopic soft scaffolds

Hung,

Cheung,

Ren

et al. 2024

Beilstein J. Org. Chem.

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In the design of photoharvesting and photoresponsive supramolecular systems in aqueous medium, the fabrication of amphiphilic photoswitches enables a noninvasive functional response through photoirradiation. Although most aqueous supramolecular assemblies are driven by high-energy and biodamaging UV light, we have previously reported a design of amphiphilic donor–acceptor Stenhouse adducts (DASAs) controlled by white light. Herein, we present a series of DASA amphiphiles (DAs) with minor structural modifications on the alkyl linker chain length connecting the DASA motif with the hydrophilic moiety. The excellent photoswitchability in organic medium and the photoresponsiveness in aqueous medium, driven by visible light, were investigated by UV–vis absorption spectroscopy. The assembled supramolecular nanostructures were confirmed by electron microscopy, while the supramolecular packing was revealed by X-ray diffraction analysis. Upon visible-light irradiation, significant transformations of the DA geometry enabled transformations of the supramolecular assemblies on a microscopic scale, subsequently disassembling macroscopic soft scaffolds of DAs. The current work shows promising use for the fabrication of visible-light-controlled macroscopic scaffolds, offering the next generation of biomedical materials with visible-light-controlled microenvironments and future soft-robotic systems.

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Photocontrolled chiral supramolecular assembly of azobenzene amphiphiles in aqueous media

Cited by 6 publications

References 62 publications

Tailoring Multicontrolled Supramolecular Assemblies of Stiff-Stilbene Amphiphiles into Macroscopic Soft Scaffolds as Cell-Material Interfaces

Tailoring Multicontrolled Supramolecular Assemblies of Stiff-Stilbene Amphiphiles into Macroscopic Soft Scaffolds as Cell-Material Interfaces

Multi-Stimuli-Responsive Water-Dispersible Magnetite Nanoparticles Using Arylazopyrazole-Modified Polymer Ligands

Supramolecular assemblies of amphiphilic donor–acceptor Stenhouse adducts as macroscopic soft scaffolds

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