Highly fluorescent photochromic diarylethene in the closed-ring form

Jeong, Yong Chul; Yang, Sung Ik; Ahn, Kyu‐Hong; Kim, Eunkyoung

doi:10.1039/b501324k

Cited by 167 publications

(83 citation statements)

References 13 publications

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“…In coordinate-stochastic superresolution modalities (STORM, [15][16] PALM, [17][18] GSDIM, [19][20] 21 ) molecular off>on events take place molecule by molecule, with the molecules located at random positions. [27][28] B. Carboxylated water-soluble photochromic and fluorescent DAEs previously used for superresolution RESOLFT imaging. 2,[22][23][24][25][26] Importantly, the coordinate-stochastic approaches, such as STORM, require the detection of fluorophores at the single molecule (SM) level.…”

Section: Introductionmentioning

confidence: 99%

Fluorescent Photoswitchable Diarylethenes for Biolabeling and Single-Molecule Localization Microscopies with Optical Superresolution

et al. 2017

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A modular assembly of water-soluble diarylethenes (DAEs), applicable as biomarkers for optical nanoscopy, is reported. Reversibly photoswitchable 1,2-bis(2-alkyl-6-phenyl-1-benzothiophene-1,1-dioxide-3-yl)perfluorocyclopentenes possessing a fluorescent "closed" form were decorated with one or two methoxy group(s) attached to the para-position(s) of phenyl ring(s) and two, four, or eight carboxylic acid groups. Antibody conjugates of these DAEs feature low aggregation, efficient photoswitching in aqueous buffers, specific staining of cellular structures, and photophysical properties (high emission efficiencies and low cycloreversion quantum yields) enabling their application in superresolution microscopy. Images of tubulin, vimentin, and nuclear pore complexes are presented. The superresolution images can also be acquired by using solely 488 nm light without additional photoactivation with UV light. These DAEs exhibit reversible photoswitching without requiring any additives to the imaging media and open new paths toward the modular design of fluorescent dyes for bioimaging with optical superresolution.

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Section: Introductionmentioning

confidence: 99%

Fluorescent Photoswitchable Diarylethenes for Biolabeling and Single-Molecule Localization Microscopies with Optical Superresolution

et al. 2017

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“…A class of sulfone form of 1,2-bis(2-methyl-1-benzothiophene-3-yl)perfluorocyclopentene was synthesized (Scheme 28) [52][53][54]. Unlike the diarylethene system, which usually is in general fluorescence in open-ring form and nonfluorescent in ring-closed form, the closed form of the sulfone dibenzothienylethene emits strong fluorescence even in the absence of extra fluorophores.…”

Section: Branchesmentioning

confidence: 99%

Molecular Structure Analysis of Photochromic Diarylethene

Chen¹

2007

COC

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Photochromic diarylethene have received considerable attention because of their potential photonic applications. All of these applications come from the fact that when stimulated with light at appropriate wavelengths, the physical and chemical properties can be reversibly modulated. During the last decade, more and more decoration on the general structures of diarylethene and novel skeletons beyond the general structures have been developed from many motivation aspects, such as seeking for facile synthetic routes, the ability to tailor the physical and chemical properties in flexible manner and etc. This article describes recent novel development of molecular structure design strategies of diarylethene.

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“…The fact that the photochromic diarylethenes in combination with FRET can modulate the fluorescence intensity indicates the possibility of applying these molecules as a reversible memory device by using the high sensitivity fluorescence detection method. 24 The thermal stability and fatigue resistance of 1 and 2…”

Section: The Fluorescence Of 1 Andmentioning

confidence: 99%

Efficient One‐step Synthesis and Properties of Photochromic Diarylethenes Having an Indene Bridging Unit

Jin

Zou

2011

Chin. J. Chem.

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Two novel isomeric photochromic diarylethenes with an indene bridging unit have been prepared by a simple and efficient one-step synthesis method. Their properties, including photochromic behavior, fluorescent properties and fatigue resistance, have been investigated. These two isomeric compounds showed photochromic back-and-forth reactions with ultraviolet and visible light both in solution and in PMMA film. Their ring-open forms exhibited appreciable fluorescence, which was quenched by the ring-closed forms. All results indicated that diarylethenes derivatives with indene-aryl bridges exhibited rather high fatigue resistance and good thermally irreversible photochromic properties.

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Highly fluorescent photochromic diarylethene in the closed-ring form

Abstract: A highly fluorescent diarylethene in the closed-ring form was synthesized by the oxidation of 1,2-bis(2-methyl-1-benzothiophene-3-yl)perfluorocyclopentene (BTF6).

Cited by 167 publications

References 13 publications

Fluorescent Photoswitchable Diarylethenes for Biolabeling and Single-Molecule Localization Microscopies with Optical Superresolution

Fluorescent Photoswitchable Diarylethenes for Biolabeling and Single-Molecule Localization Microscopies with Optical Superresolution

Molecular Structure Analysis of Photochromic Diarylethene

Efficient One‐step Synthesis and Properties of Photochromic Diarylethenes Having an Indene Bridging Unit

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