Fluorescent Switches Based on Photochromic Compounds

Cusido, Janet; Deni̇z, Erhan; Raymo, Françisco M.

doi:10.1002/ejoc.200801244

Cited by 175 publications

(87 citation statements)

References 133 publications

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“…It follows that the photogenerated state of the photochromic component can, eventually, be excited selectively at an appropriate λ Ex . If this species is fluorescent, then its emission is observed after activation at a λ Ac designed to trigger the photochromic transformation and illumination at λ Ex to excite the photogenerated state [87][88][89][90][91][92][93][94]. This behavior is identical to that associated with the photoinduced conversion of 1a into 1b except for the fact that the photochromic process is reversible.…”

Section: Mechanisms and Structural Designs For Reversible Fluorescencmentioning

confidence: 93%

“…Alternatively a preformed fluorophore can be connected to an appropriate photochromic component and the photoinduced interconversion of the latter can be exploited to control the emission of the former [87,[89][90][91][92][93][94]. Indeed, numerous examples of fluorophore-photochrome dyads have already been developed successfully, relying on this general design logic .…”

Section: Mechanisms and Structural Designs For Reversible Fluorescencmentioning

confidence: 99%

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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: 93%

Section: Mechanisms and Structural Designs For Reversible Fluorescencmentioning

confidence: 99%

Photoactivatable Fluorophores

Raymo

2012

ISRN Physical Chemistry

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“…While there are both inorganic and organic photochromic materials, organic photochromic dyes are the most popular, having a wide range of uses from decoration and eyeglass lens coatings to optical switches and data storage. There are a number of photochromic dyes and various mechanisms that cause their photochromic transformations, and these have been extensively reviewed [146][147][148][149][150]. Of these, spiro-based (e.g., spiropyran) and increasingly diarylethene-based photoswitchable compounds have found particular application in FRET, so-called photochromic FRET (pcFRET) [147,149,[151][152][153].…”

Section: Photochromic Dyesmentioning

confidence: 99%

“…There are a number of photochromic dyes and various mechanisms that cause their photochromic transformations, and these have been extensively reviewed [146][147][148][149][150]. Of these, spiro-based (e.g., spiropyran) and increasingly diarylethene-based photoswitchable compounds have found particular application in FRET, so-called photochromic FRET (pcFRET) [147,149,[151][152][153]. The pcFRET technique is particularly useful in FRET imaging applications, especially on a single-protein level, where pcFRET can be used to turn the FRET process "off" or "on" thereby creating an internal control and eliminating false-positive or false-negative signals due to high intrinsic autofluorescence, interactions with other endogenous proteins, and/ or low FRET efficiencies [152,[154][155][156][157].…”

Section: Photochromic Dyesmentioning

confidence: 99%

Materials for FRET Analysis: Beyond Traditional Dye–Dye Combinations

Sapsford

Wildt

Mariani

et al. 2013

FRET – Förster Resonance Energy Transfer

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The intrinsic sensitivity (r 6 dependence) of F€ orster (or fluorescence) resonance energy transfer (FRET) to nanoscale changes in the donor/acceptor separation distance has made FRET an invaluable biophysical tool in a variety of applications, ranging from studying the structure and conformation of proteins and nucleic acids to examining biomolecular interactions, including its use in in vitro and in vivo bioassays [1][2][3][4][5][6][7]. While the myriad of FRET configurations and techniques currently in use are covered throughout this book, here we focus primarily on the materials utilized as donor or acceptor probes in FRET rather than the process itself [3,5,8,9]. Our 2006 review paper on this topic serves as the foundation for this updated chapter [3]. The materials were divided into three main categories: organic materials that include "traditional" dye fluorophores, dark quenchers, polymers, and carbon nanomaterials (NMs); inorganic materials such as metal chelates, metal, and semiconductor nanocrystals; and fluorophores of biological origin such as fluorescent proteins (FPs), amino acids, and fluorescence generated from enzymatic bioluminescence (BL) and chemiluminescence (CL). These materials may function as FRET donors and/or acceptors, depending upon experimental design. Many of the new materials developed and/or new donor-acceptor probe combinations used address some of the inherent complications of more traditional FRET materials, including photobleaching, spectral cross talk, and direct excitation of the acceptor species, and examples of these will be highlighted and discussed throughout the chapter. Since the vast majority of FRET applications are biological in nature, they routinely involve some type of biomolecule labeling strategy, which ultimately plays a significant and fundamental role in the success and interpretation of the resulting FRET. Therefore, we begin the chapter with a brief discussion of the bioconjugation techniques commonly utilized for FRET and points to consider, followed by sections highlighting the current and emerging materials that are used, or have the potential to be used, in FRET applications.

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“…15,16 Toggling the photoresponsive chromophore between two isomers where only one of the isomers can act as an efficient energy-transfer acceptor, allows control over quenching of the fluorescence from the probe through Förster Resonance Energy Transfer (FRET) and other mechanisms. The result is the creation of an emissive state and a quenched state that can be alternated by exposure of the photoresponsive chromophore to different wavelengths of light.…”

Section: Introductionmentioning

confidence: 99%

A 'Plug and Play' Method to Create Water-dispersible Nanoassemblies Containing an Amphiphilic Polymer, Organic Dyes and Upconverting Nanoparticles

Arafeh

Asadirad

et al. 2015

JoVE

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In this protocol, we first describe a procedure to synthesize lanthanide doped upconverting nanoparticles (UCNPs). We then demonstrate how to generate amphiphilic polymers in situ, and describe a protocol to encapsulate the prepared UCNPs and different organic dye molecules (porphyrins and diarylethenes) using polymer shells to form stable water-dispersible nanoassemblies. The nanoassembly samples containing both the UCNPs and the diarylethene organic dyes have interesting photochemical and photophysical properties. Upon 365 nm UV irradiation, the diarylethene group undergoes a visual color change. When the samples are irradiated with visible light of another specific wavelength, the color fades and the samples return to the initial colorless state. The samples also emit visible light from the UCNPs upon irradiation with 980 nm near-infrared light. The emission intensity of the samples can be tuned through alternate irradiation with UV and visible light. Modulation of fluorescence can be performed for many cycles without observable degradation of the samples. This versatile encapsulation procedure allows for the transfer of hydrophobic molecules and nanoparticles from an organic solvent to an aqueous medium. The polymer helps to maintain a lipid-like microenvironment for the organic molecules to aid in preservation of their photochemical behavior in water. Thus this method is ideal to prepare water-dispersible photoresponsive systems. The use of near-infrared light to activate upconverting nanoparticles allows for lower energy light to be used to activate photoreactions instead of more harmful ultraviolet light.

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Fluorescent Switches Based on Photochromic Compounds

Cited by 175 publications

References 133 publications

Photoactivatable Fluorophores

Photoactivatable Fluorophores

Materials for FRET Analysis: Beyond Traditional Dye–Dye Combinations

A 'Plug and Play' Method to Create Water-dispersible Nanoassemblies Containing an Amphiphilic Polymer, Organic Dyes and Upconverting Nanoparticles

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