Rapid amplitude-modulation of a diarylethene photoswitch: en route to contrast-enhanced fluorescence imaging

Naren, Gaowa; Larsson, Wera; Benítez-Martín, Carlos; Li, Shiming; Pérez‐Inestrosa, Ezequiel; Albinsson, Bo; Andréasson, Joakim

doi:10.1039/d1sc01071a

Cited by 23 publications

(15 citation statements)

References 33 publications

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“…Numerous photoswitchable fluorescent DAEs have been reported to date, and the main challenge is their extremely low water solubility. Several examples of fluorescent DAEs in living cells and organisms have been reported, [50][51][52][53][54] exploiting strategies to improve solubility such as the introduction of polyethylene glycol chains or charged species. Despite these efforts, only a few of these reports provide characterisation in aqueous conditions, suggesting significant aggregation issues, and the majority function in fluorescence turn-off mode.…”

Section: Intrinsically Fluorescent Photoswitchesmentioning

confidence: 99%

Small-molecule photoswitches for fluorescence bioimaging: engineering and applications

Olesińska-Mönch

Deo

2023

Chem. Commun.

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Section: Intrinsically Fluorescent Photoswitchesmentioning

confidence: 99%

Small-molecule photoswitches for fluorescence bioimaging: engineering and applications

Olesińska-Mönch

Deo

2023

Chem. Commun.

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“…Classical strategies usually require the design of a suitable molecular switch to control the RET process between the switch and various fluorophores (donor-acceptor pairs) according to external stimuli, [4,43b] so that the emission state can be regulated on demand. Andreasson et al [193] reported that the emission of water-soluble DAE derivatives is allowed to be quickly switched using an amplitude-modulated red light with a longer wavelength than that absorbed by the fluorescent species. That example shows great potential for optical lockin detection imaging with high contrast [194] and also provides ideas for overcoming interference from undesired background fluorescence when imaging biological tissues.…”

Section: Bioimagingmentioning

confidence: 99%

“…Andreasson et al. [ 193 ] reported that the emission of water‐soluble DAE derivatives is allowed to be quickly switched using an amplitude‐modulated red light with a longer wavelength than that absorbed by the fluorescent species. That example shows great potential for optical lock‐in detection imaging with high contrast [ 194 ] and also provides ideas for overcoming interference from undesired background fluorescence when imaging biological tissues.…”

Section: Changes In the Physical And Chemical Properties Of Daementioning

confidence: 99%

Future‐Oriented Advanced Diarylethene Photoswitches: From Molecular Design to Spontaneous Assembly Systems

et al. 2022

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cycloreversion of DAE under light irradiation produces many exciting functional effects, such as changes in photophysical and photochemical properties, [12] changes in the shape or mechanical properties of the solid, [13] electrical conductivity, [7b,14] and the generation of reactive oxygen species (ROS). [15] This type of photochromic compound can be considered a stilbene derivative. At this time, the most widely known and systematically studied DAE derivative structure contains two aryl groups and a benzene ring (usually two identical or different thiophene units with low aromatic stabilization energy [16] ) and a five-membered ring of perfluorocyclopentene and cyclopentene units [17] where the ethene bridge is located, which significantly improve photochromism. [18] In essence, the DAE photoisomerization process is a reversible electrocyclic reaction of the central 6π-electron systems. [2] Under light irradiation, DAE can rapidly and reversibly transform between its open and closed forms, and that transformation is accompanied by a color change caused by a change in the π-conjugation distribution. [2] The important thing is that the colorless opened-and colored closed-ring isomers are both thermally stable; that is, cyclization and cycloreversion do not proceed spontaneously in the dark; they need to be driven by external light irradiation at specific wavelengths. [2,19] Compared with classic lightresponsive molecules such as azobenzene, [20] the light intensity required to drive the isomerization of DAE is relatively low. Moreover, even after multiple cycles, the photochromic performance does not show significant fatigue in either the solution or solid state. [2,18b,21] DAE research to this point can be roughly divided into three stages in chronological order: early exploration of DAE's molecular structure and theory, nearly two decades of purpose-oriented molecular structure modification research, and about ten years of research into practical applications of DAE in assembly systems. Research before about 2000 focused mainly on developing more abundant DAE-derivative structures and advancing the systematic understanding of DAE's physical and chemical properties and switching performance. To regulate its switching performance and give it new functionality, many strategies for modifying the ethene bridge and aryl groups of DAE have been proposed. [22] In the first two research stages, the mechanisms and structural modification of DAE isomerization were thoroughly and systematically explored, and countless important Diarylethene (DAE) photoswitch is a new and promising family of photochromic molecules and has shown superior performance as a smart trigger in stimulus-responsive materials. During the past few decades, the DAE family has achieved a leap from simple molecules to functional molecules and developed toward validity as a universal switching building block. In recent years, the introduction of DAE into an assembly system has been an attractive strategy that enables the photochromic behavior of the b...

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“…7 Recently, the combination of DTE photoswitching and a fluorescent unit has become a kind of appealing fluorescence switch arising from their thermo-stability, robust fatigue resistance and rapid response. 8–11 A general scheme for designing such switches is a dyad system comprising one fluorophore and DTE unit in the same molecule, facilitating fluorescence quenching through intramolecular energy transfer (ET). 12 As depicted in Scheme 1a, the ring-open state of DTE with high S 1 energy restrains the energy transfer from the excited fluorophore to the open isomer, retaining the fluorescence emission of the fluorophore.…”

Section: Introductionmentioning

confidence: 99%

Green-/NIR-light-controlled rapid photochromism featuring reversible thermally activated delayed fluorescence and photoelectronic switching

Zhang

Tian

et al. 2022

Chem. Sci.

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Rapid amplitude-modulation of a diarylethene photoswitch: en route to contrast-enhanced fluorescence imaging

Abstract: A water soluble diarylethene (DAE) derivative that displays exceptionally intense fluorescence from the colorless open form has been synthesized and characterized using UV/vis spectroscopy and fluorescence microscopy. We show that...

Cited by 23 publications

References 33 publications

Small-molecule photoswitches for fluorescence bioimaging: engineering and applications

Small-molecule photoswitches for fluorescence bioimaging: engineering and applications

Future‐Oriented Advanced Diarylethene Photoswitches: From Molecular Design to Spontaneous Assembly Systems

Green-/NIR-light-controlled rapid photochromism featuring reversible thermally activated delayed fluorescence and photoelectronic switching

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