Photoactivatable Fluorophores for Super-Resolution Imaging Based on Oxazine Auxochromes

Deni̇z, Erhan; Tomasulo, Massimiliano; Cusido, Janet; Yildiz, İbrahim; Petriella, Marco; Bossi, Mariano L.; Sortino, Salvatore; Raymo, Françisco M.

doi:10.1021/jp211796p

Cited by 125 publications

(121 citation statements)

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“…As a result, the behavior of these functional compounds translates into fluorescence deactivation. A remarkable exception is a family of dyads specifically designed for fluorescence activation [128][129][130]. In these compounds, the photochromic component regulates reversibly the ability of the fluorescent fragment to absorb at λ Ex and permits the implementation of an activation mechanism similar to that governing the behavior of 1a.…”

Section: Mechanisms and Structural Designs For Reversible Fluorescencmentioning

confidence: 99%

Photoactivatable Fluorophores

Raymo

2012

ISRN Physical Chemistry

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Photoactivatable fluorophores switch from a nonemissive to an emissive state upon illumination at an activating wavelength and then emit after irradiation at an exciting wavelength. The interplay of such activation and excitation events can be exploited to switch fluorescence on in a defined region of space at a given interval of time. In turn, the spatiotemporal control of fluorescence translates into the opportunity to implement imaging and spectroscopic schemes that are not possible with conventional fluorophores. Specifically, photoactivatable fluorophores permit the monitoring of dynamic processes in real time as well as the reconstruction of images with subdiffraction resolution. These promising applications can have a significant impact on the characterization of the structures and functions of biomolecular systems. As a result, strategies to implement mechanisms for fluorescence photoactivation with synthetic fluorophores are particularly valuable. In fact, a number of versatile operating principles have already been identified to activate the fluorescence of numerous members of the main families of synthetic dyes. These methods are based on either the irreversible cleavage of covalent bonds or the reversible opening and closing of rings. This paper overviews the fundamental mechanisms that govern the behavior of these photoresponsive systems, illustrates structural designs for fluorescence photoactivation, and provides representative examples of photoactivatable fluorophores in actions.

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Section: Mechanisms and Structural Designs For Reversible Fluorescencmentioning

confidence: 99%

Photoactivatable Fluorophores

Raymo

2012

ISRN Physical Chemistry

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“…These compounds fuse 2H,3H-indole and benzooxazine heterocycles within a single covalent skeleton. One member of the developed group was doped into macromolecules that has hydrophilic poly(ethylene glycol) chains and hydrophobic decyl arms appended to a common poly(methacrylate) backbone providing a relatively nonpolar environment (average size: 14 nm) [88].…”

Section: Doping Polymer Nanoparticlesmentioning

confidence: 99%

“…Fluorescence detection can be used in non-destructive recording and detection [10,71,91] and bio-imaging [24,78,80,32,63,88], because it requires a much lower power light source than absorption detection. A candidate molecule for a non-destructive readout should possess the ability to turn fluorescence "on" or "off" by photostimulation, while the excitation should not induce ring opening or ring closure of the photochrome.…”

Section: Fluorescence In Connection With Photochromismmentioning

confidence: 99%

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Organic Nanoparticulate Photochromes

Feczkó¹,

Vončina²

2013

COC

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Photochromic organic dyes can be widely used in materials for optically rewritable data storage, photonic switches, memories, sensors, or actuators. In recent years photochromic materials based on nanoparticles became particularly focused, since they can be dispersed in colloidal aqueous suspensions or incorporated in thin films, avoiding problems of light scattering or shallow light penetration in bulk materials. Spiropyrans, spirooxazines and diarylethenes were by far the most researched photochromes in nanoparticulate systems. Great effort was made to investigate photochromic dyes incorporated into organic nanoparticles via self-assembly strategies, covalent linkage or dispersion of the molecular species in polymers (doping). Nanoparticles composed of solely photochromic dyes were prepared by laser ablation and reprecipitation techniques. Photochromic dyes were microencapsulated by self-assembly, soap free-, emulsion/microemulsion/miniemulsion or free radical-(co)polymerization. Sol-gel processing from silane precursors to poly(organo)siloxane matrix is a common method to synthesize doped or core-shell photochromic organogels. Coloured forms of some photochromes display fluorescence; however, a more effective strategy for fluorescence modulation with photochromic molecules is integrating them, covalently or noncovalently, with a separate fluorophore in the same nanoparticles. These photoresponsive nanoparticles may find applications particularly in biological fields such as cell labelling and bioimaging. The purpose of this review is to summarize the preparation methods of organic nanoparticles containing photochromic dyes and to investigate their typical properties derived from their nanoparticulate character.Keywords: photochromic nanoparticle, laser ablation, reprecipitation, polymerization, doping, fluorescence INTRODUCTIONPhotochromism is a reversible structural and colour change of a species triggered in one or both directions by electromagnetic radiation [1]. The shift of optical absorption, due to change in molecular structure or conformation results in colourization, while the coloured product decolourizes after a structure rearrangement in the back (generally thermal) reaction. The reversible transformations of photochromic compounds are usually based on ring opening/closing steps, cis/trans isomerizations, proton transfer, electron transfer or cycloadditions [2]. Like other stimuli responsive materials (e.g. heat and pH-sensitive materials), photochromic devices are responsive to an external stimulus, in this case, light. Light is the most attractive stimulus due to the fact that its wavelength, intensity and focus can be tuned. Photochromic materials have been investigated extensively during the past few decades because of optical responses and nonlinear optical, electronic and magnetic properties [3]. Photochromic materials have a high potential for applications to ophthalmic lenses [4,5] [15], and also for microstructuring and patterning surfaces [16]. Therefore, photosensitive, nanoscal...

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“…Although several turn-on mode photoactivatable fluorophores, such as dihydrofuran, 41 coumarine, 42 fluorescein, 43 rhodamine 44 and anthracene, 45 have been reported, their photoactivation quantum yields are relatively low and the reactions are irreversible. Recently, a new type of turn-on mode photoswitchable fluorescent molecules has been developed.…”

Section: Introductionmentioning

confidence: 99%

Photoswitchable Turn-on Mode Fluorescent Diarylethenes: Strategies for Controlling the Switching Response

Irie

Morimoto

2017

Bulletin of the Chemical Society of Japan

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University. He has been conducting research on molecular photoswitches for the last 40 years. In the middle of the 1980s he discovered thermally irreversible and fatigue resistant photochromic diarylethenes. His current interests focus on the development of light-driven molecular-crystal actuators and turn-on mode fluorescent diarylethenes for super-resolution fluorescence microscopies. Masakazu Morimoto AbstractA new type of photoswitchable fluorescent diarylethenes, which have no fluorophore unit but emit strong fluorescence (¯f ³ 0.9) in the closed-ring isomers, has been developed. They are sulfone derivatives of 1,2-bis(2-alkyl-4-methyl-5-phenyl-3-thienyl)perfluorocyclopentenes and 1,2-bis(2-alkyl-1-benzothiophen-3-yl)perfluorocyclopentenes. By chemical modifications of the structures their switching response was tuned to meet the requirements for super-resolution fluorescence microscopies. The water-soluble derivatives have been successfully applied to acquire super-resolution bioimages using a single-wavelength visible beam.Fluorescence is the most convenient tool to detect small amounts of molecules.1 Even single molecules can be detected using fluorescence owing to remarkable progress of optical detection techniques. 24 Various types of highly fluorescent chromophores have been synthesized and widely applied in materials and life sciences, such as microanalysis and bioimaging.59 Their application is expected to be further extended when an additional switching property is provided to the chromophores. 10 The changes in fluorescence spectra and/or intensity by external stimuli, such as chemicals, electrons (or holes) or photons, are ingeniously adopted for analysis and imaging. When the fluorescence is photoactivated or switched on and off upon photoirradiation, the fluorescence modulation offers the opportunities to monitor diffusion processes in real time, 1113 store optical information in memory media, 1420 and increase the resolution in imaging. 10,2023 There are two types of fluorescence switching molecules, photoactivatable and photoswitchable ones. The photoactivatable molecules irreversibly switch from non-fluorescent to fluorescent states, while photoswitchable ones undergo reversible switching between fluorescent and non-fluorescent states. The reversibly photoswitchable molecules can be designed and constructed by integrating both photochromic and fluorescent chromophores in a molecule. 1420 Based on this strategy

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Photoactivatable Fluorophores for Super-Resolution Imaging Based on Oxazine Auxochromes

Cited by 125 publications

References 148 publications

Photoactivatable Fluorophores

Photoactivatable Fluorophores

Organic Nanoparticulate Photochromes

Photoswitchable Turn-on Mode Fluorescent Diarylethenes: Strategies for Controlling the Switching Response

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