The effect of a “push—pull” structure on the turn-on fluorescence of photochromic thio-ketone type diarylethenes

Pang, Shichong; Jang, Daeun; Lee, Woo Sun; Kang, Hyeok-Mo; Hong, Seung-Ju; Hwang, Sung Kwan; Ahn, Kwang‐Hyun

doi:10.1039/c4pp00320a

Cited by 7 publications

(3 citation statements)

References 55 publications

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“…In turn, the possibility to switch fluorescence with optical inputs offers the opportunity to overcome the limitations that diffraction imposes on the spatial resolution of conventional fluorescence images. − As a result, mechanisms for the optical control of fluorescence with photochromic compounds can ultimately evolve into invaluable operating principles for the visualization of biological specimens with unprecedented resolution. Indeed, representative examples of photochromic probes with optimal properties for subdiffraction imaging have been designed already, relying on diarylethenes, − imidazole dimers, rhodamines, − and spiropyrans. − We developed a family of fast and stable photochromic compounds based on the photoinduced opening and thermal closing of an oxazine ring. − We demonstrated that their reversible interconversion can be exploited to control the efficiency of electron- and energy-transfer processes and switch the emission of fluorescent partners. , Additionally, the structural changes associated with the photoinduced opening of the oxazine ring can be engineered to control reversibly the electronic structure of a covalently connected fluorophore. − These transformations alter the ability of the latter to absorb exciting photons and emit as a result. In fact, our mechanism for fluorescence photoactivation can be replicated at the single-molecule (SM) level to allow the stochastic reconstruction − of images with spatial resolution at the nanoscale. ,, …”

Section: Introductionmentioning

confidence: 99%

A Photochromic Bioconjugate with Photoactivatable Fluorescence for Superresolution Imaging

et al. 2016

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A coumarin fluorophore and an oxazine photochrome can be integrated within the same molecular skeleton and connected covalently to a secondary antibody. Illumination of the antibody−dyad conjugate at an appropriate activation wavelength opens the oxazine ring reversibly and shifts bathochromically the ground-state absorption of the coumarin component. Selective excitation of the photochemical product then produces significant fluorescence and allows the detection of activated bioconjugates at the single-molecule level. Such fluorescence activation events can be exploited to resolve temporally individual emitters and reconstruct images of immunolabeled cells with subdiffraction resolution. Relying on a similar conjugation protocol, a model compound, incorporating the same chromophore of the photochemical product, can also be connected covalently to a secondary antibody. Stimulated emission can be exploited to deplete the excited state of the bioconjugated chromophores and switch their fluorescence off. These operating principles for fluorescence switching also permit the imaging of immunolabeled cells with subdiffraction resolution. Thus, these photoswitchable molecules, in combination with the labeling ability of antibodies, can evolve into valuable probes for bioimaging with superresolution.

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Section: Introductionmentioning

confidence: 99%

A Photochromic Bioconjugate with Photoactivatable Fluorescence for Superresolution Imaging

et al. 2016

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“…[15] The fluorescenceoft he compound was thought to be due to the bridge unit containing the six-membered ring with sulfur and carbonyl groups forming a" push-pull" system. [16] Thus, to improve the photochromic properties, and especially the fluorescenceo fd iarylethene 1,aseries of derivatives, 2-7,r etaining the "push-pull system" was synthesized,a nd their photophysical properties were studied. Interestingly,d uring our study with 1-7,w eunexpectedly found that the diarylethenes had electrochromic properties.…”

Section: Introductionmentioning

confidence: 99%

“…Recently, we reported a novel “turn‐on” fluorescent diarylethene—2,3‐bis(2‐methylbenzo[ b ]thiophen‐3‐yl)‐5,6‐dihydro‐4 H ‐thieno[2,3‐ b ]thiopyran‐4‐one ( 1 )—and its successful application to live cell imaging (Scheme ). [15] The fluorescence of the compound was thought to be due to the bridge unit containing the six‐membered ring with sulfur and carbonyl groups forming a “push–pull” system 16. Thus, to improve the photochromic properties, and especially the fluorescence of diarylethene 1 , a series of derivatives, 2 – 7 , retaining the “push–pull system” was synthesized, and their photophysical properties were studied.…”

Section: Introductionmentioning

confidence: 99%

Photoswitchable “Turn‐on” Fluorescence Diarylethenes: Substituent Effects on Photochemical Properties and Electrochromism

Pang

Ahn

2015

Chemistry A European J

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A series of "turn-on" fluorescence diarylethenes derived from 2,3-bis(2-methylbenzo[b]thiophen-3-yl)-5,6-dihydro-4H-thieno[2,3-b]thiopyran-4-one (1) with alkyl and acetyl substituents were synthesized. The photochemical and photophysical properties of these derivatives, including the photoreaction of crystalline 1, were thoroughly investigated to reveal substituent effects on their properties. The results indicated that alkyl substituents did not significantly affect the absorption and emission spectra of the diarylethenes. However, large absorption and emission wavelength shifts were observed for the diarylethene with an acetyl substituent due to extension of π-π conjugation. Significantly, all of the fluorescent ring-closed forms of the compounds isomerized to their ring-open forms in the presence of Cu(2+) in the dark. EPR results provide clear evidence for the formation of the compound 1 radical cation intermediate that might be generated in the reaction between c-1 and Cu(2+) . DFT calculations found that the ground-state activation energy for ring-opening of 1(.+) was approximately 9.2 kcal mol(-1) lower than that of 1 without Cu(2+) , such that a Cu(2+) -catalyzed oxidative cycloreversion reaction at room temperature might be possible.

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Multicolor Fluorescence Photoswitching: Color‐Correlated versus Color‐Specific Switching

Kim

Park

2018

Advanced Optical Materials

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Fluorescence photoswitching systems using photochromic molecules, which turn on and off their fluorescence upon light irradiation, have emerged as highly promising material systems during the past two decades related to their optoelectronic applications such as high‐density optical memory, bioimaging, and super‐resolution microscopy. Single‐color fluorescence photoswitching, which provides only two different states (on/off), is limited in terms of its practical applications such as interference from autofluorescence in biological applications and limited switching states in logic gate and optical memory applications. To address such issues, studies on multicolor fluorescence photoswitching systems incorporating photochromic molecules have witnessed an explosive growth in the past decade in terms of the academic principles and technological applications. In the earlier part, this review briefly introduces the principle of fluorescence photoswitching based on the representative single‐color fluorescence photoswitching systems. Then, the review turns into the main topic of multicolor fluorescence photoswitching systems which are organized in two different subcategories of 1) color‐correlated photoswitching and 2) color‐specific photoswitching. Not only the material systems and principles of the multicolor fluorescence photoswitching, but also their important applications are described and discussed here. In the last section of this review, a brief summary and outlook on the future development are provided.

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The effect of a “push—pull” structure on the turn-on fluorescence of photochromic thio-ketone type diarylethenes

Cited by 7 publications

References 55 publications

A Photochromic Bioconjugate with Photoactivatable Fluorescence for Superresolution Imaging

A Photochromic Bioconjugate with Photoactivatable Fluorescence for Superresolution Imaging

Photoswitchable “Turn‐on” Fluorescence Diarylethenes: Substituent Effects on Photochemical Properties and Electrochromism

Multicolor Fluorescence Photoswitching: Color‐Correlated versus Color‐Specific Switching

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