A trident dithienylethene-perylenemonoimide dyad with super fluorescence switching speed and ratio

Li, Chong; Yan, Hui; Zhao, Ling-Xi; Zhang, Guofeng; Hu, Zhe; Huang, Zhen-Li; Zhu, Ming‐Qiang

doi:10.1038/ncomms6709

Cited by 144 publications

(93 citation statements)

References 34 publications

(39 reference statements)

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“…Vis. [29][30][31][32][33][34][35][36][37] . Some of these derivatives can achieve reversible fluorescence photoswitching even at the singlemolecule level [31][32][33] .…”

Section: Molecular Systems Consisting Of Fluorescent and Photochromicmentioning

confidence: 99%

Photochromic fluorophores at the molecular and nanoparticle levels: fundamentals and applications of diarylethenes

2018

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Fluorescent molecules and materials are widely used in many areas in physics, chemistry, and biology as emitters, tags, or sensors. The possibility of controlling their fluorescence signal by light, namely, fluorescence photoswitching, down to the nanoscale level can then dramatically extend their fields of applications. This review focuses on fluorescent and photochromic diarylethene-based nanosystems. The choice of the diarylethene family has been driven by its excellent photoswitching properties (conversion yield, bistability, fatigue resistance), which make them fully appropriate when high-performance behavior is required. The different molecular and nanomaterial designs providing suitable combinations of fluorescence and photochromism are summarized. Besides the inherently fluorescent diarylethene molecules, chemical association between photochromic and fluorescent molecular units can advantageously lead to fluorescence photoswitching thanks to resonance energy transfer or intramolecular electron transfer processes. Furthermore, the preparation of nanoscale emissive materials involving diarylethene units paves the way to new interesting features, such as near-infrared control of emissive and photoswitchable nanohybrids, giant amplification of the fluorescence photoswitching in organic nanoparticles, or fluorescence color modulation. Many applications derived from such fluorescent diarylethene-based molecules and nanomaterials have been developed recently, especially in the field of biology for fluorescence biolabeling and super-resolution imaging but also for photocontrol of biological functions. Extremely promising prospects are expected in the near future.

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“…Vis. [29][30][31][32][33][34][35][36][37] . Some of these derivatives can achieve reversible fluorescence photoswitching even at the singlemolecule level [31][32][33] .…”

Section: Molecular Systems Consisting Of Fluorescent and Photochromicmentioning

confidence: 99%

Photochromic fluorophores at the molecular and nanoparticle levels: fundamentals and applications of diarylethenes

2018

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“…[20][21][22] Despite their wide variability,t he lack of derivatives in which the closed form has astrong fluorescence in the visible range has prevented their direct application in super-resolution imaging. Strategies to covalently link diarylethene switches with suitable fluorophores and to utilize the energy [23] or electron transfer [24] of the resulting multichromophoric systems have been successful, but require extended syntheses and result in rather large probes.L abeling structures with such extended probes can significantly alter the structures to be visualized. [23,25] As an alternative,s uitable modification of the diarylethene photoswitch itself could give direct access to the envisioned properties.Uno et al [26] und Gillanders et al [27] have reported that the closed form of photochromic diarylethene derivatives bearing sulfone groups can fluoresce,w hich inspired our research.…”

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confidence: 99%

Nanoscopic Visualization of Soft Matter Using Fluorescent Diarylethene Photoswitches

et al. 2016

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The in situ imaging of soft matter is of paramount importance for a detailed understanding of functionality on the nanoscopic scale. Although super-resolution fluorescence microscopy methods with their unprecedented imaging capabilities have revolutionized research in the life sciences, this potential has been far less exploited in materials science. One of the main obstacles for a more universal application of superresolved fluorescence microscopy methods is the limitation of readily available suitable dyes to overcome the diffraction limit. Here, we report a novel diarylethene-based photoswitch with a highly fluorescent closed and a nonfluorescent open form. Its photophysical properties, switching behavior, and high photostability make the dye an ideal candidate for photoactivation localization microscopy (PALM). It is capable of resolving apolar structures with an accuracy far beyond the diffraction limit of optical light in cylindrical micelles formed by amphiphilic block copolymers.The nanoscopic structure of soft-matter materials determines their properties. [1] Therefore, methods to directly visualize structures in the nanometer range are of paramount importance for the ongoing evolution of novel materials with specialized and adaptive properties for sophisticated applications. Scanning probe microscopy techniques give access to the nanometer range and determine surface properties such as topology and softness, [2,3] while modern electron microscopy methods, such as scanning electron microscopy (SEM) [4,5] and transmission electron microscopy (TEM), [6][7][8] can yield structural information even in the subnanometer range when there is sufficient electron density contrast. Despite the success of these methods, they are technically demanding and time-consuming. Furthermore, many softmatter samples possess poor electron contrast, and require non-invasive in situ imaging below the surface as well as the possibility to directly study dynamics. In recent years, superresolved fluorescence microscopy has revolutionized optical imaging, [9][10][11][12][13][14] by utilizing the photophysical or photochemical switching of fluorescent dyes in a sophisticated manner in combination with modern optics. So far, the life sciences have benefited, in particular, from the new possibilities of resolving structures well beyond the diffraction limit of light. Only a few examples of the application of super-resolution microscopy to materials science have been reported, [15][16][17][18] since concepts that require, for example, the addition of (polar) switching buffers often fail for these systems. Therefore, the main bottleneck for more universal applications of super-resolution imaging are switchable dyes with suitable (photo-)physical and chemical properties, such as high photostability, adjustable switching rates, minimum interaction with the environment to be probed, and simple design, with the possibility of multiple and straightforward derivatization for the specific labeling of structures or compartments. [19] ...

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“…The results indicated that the reversibly photoswitchable fluorescence property of PFPNs can be instantly used to fabricate photorewritable fluorescence patterning under the help of photomask. 18 MTT Assay and Confocal Imaging of PFPNs in Living Cells. The cytotoxicity of PFPNs (NP-N3) was estimated via MTT assay by using A549 cells.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Amphiphilic BODIPY-Based Photoswitchable Fluorescent Polymeric Nanoparticles for Rewritable Patterning and Dual-Color Cell Imaging

et al. 2015

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Photoswitchable fluorescent polymeric nanoparticles (PFPNs) with controllable molecular weight, high contrast, biocompatibility, and prominent photostability are highly desirable but still scarce for rewritable printing, superresolution bioimaging, and rewritable data storage. In this study, novel amphiphilic BODIPY-based PFPNs with considerable merits are first synthesized by a facile onepot RAFT-mediated miniemulsion polymerization method. The polymerization is performed by adopting polymerizable BODIPY and spiropyran derivatives, together with MMA as monomer, and mediated by utilizing biocompatible PEO macro-RAFT agent as both control agent and reactive stabilizer. The amphiphilic BODIPY-based PFPNs not only exhibit reversibly photoswitchable fluorescence properties under the alternative UV and visible light illumination through induced intraparticle fluorescence resonance energy transfer (FRET) but also display controllable molecular weight with narrow polydispersity index (PDI), high contrast of fluorescence, tunable energy transfer efficiency, good biocompatibility, excellent photostability, favorable photoreversibility, etc. The as-prepared PFPNs are successfully demonstrated for rewritable fluorescence patterning and high-contrast dual-color fluorescence imaging of living cells, implying its potential for rewritable data storage and broad biological applications in cell biology and diagnostics.

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A trident dithienylethene-perylenemonoimide dyad with super fluorescence switching speed and ratio

Cited by 144 publications

References 34 publications

Photochromic fluorophores at the molecular and nanoparticle levels: fundamentals and applications of diarylethenes

Photochromic fluorophores at the molecular and nanoparticle levels: fundamentals and applications of diarylethenes

Nanoscopic Visualization of Soft Matter Using Fluorescent Diarylethene Photoswitches

Amphiphilic BODIPY-Based Photoswitchable Fluorescent Polymeric Nanoparticles for Rewritable Patterning and Dual-Color Cell Imaging

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