Photoswitchable fluorescent diheteroarylethenes: substituent effects on photochromic and solvatochromic properties

Gillanders, Florencia; Giordano, Luciana; Dı́az, Sebastián A.; Jovin, Thomas M.; Jares‐Erijman, Elizabeth A.

doi:10.1039/c3pp50374g

Cited by 41 publications

(51 citation statements)

References 53 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…[23,25] As an alternative, suitable modification of the diarylethene photoswitch itself could give direct access to the envisioned properties. Uno et al [26] und Gillanders et al [27] have reported that the closed form of photochromic diarylethene derivatives bearing sulfone groups can fluoresce, which inspired our research.Here, we present a novel photochromic diarylethene photoswitch for super-resolution microscopy that has a high photostability and strong fluorescence in its closed form. We investigate its photophysical and photochemical properties in solution and in polymers.…”

mentioning

confidence: 85%

See 1 more Smart Citation

Nanoscopic Visualization of Soft Matter Using Fluorescent Diarylethene Photoswitches

et al. 2016

View full text Add to dashboard Cite

The in situ imaging of soft matter is of paramount importance for a detailed understanding of functionality on the nanoscopic scale. Although super-resolution fluorescence microscopy methods with their unprecedented imaging capabilities have revolutionized research in the life sciences, this potential has been far less exploited in materials science. One of the main obstacles for a more universal application of superresolved fluorescence microscopy methods is the limitation of readily available suitable dyes to overcome the diffraction limit. Here, we report a novel diarylethene-based photoswitch with a highly fluorescent closed and a nonfluorescent open form. Its photophysical properties, switching behavior, and high photostability make the dye an ideal candidate for photoactivation localization microscopy (PALM). It is capable of resolving apolar structures with an accuracy far beyond the diffraction limit of optical light in cylindrical micelles formed by amphiphilic block copolymers.The nanoscopic structure of soft-matter materials determines their properties. [1] Therefore, methods to directly visualize structures in the nanometer range are of paramount importance for the ongoing evolution of novel materials with specialized and adaptive properties for sophisticated applications. Scanning probe microscopy techniques give access to the nanometer range and determine surface properties such as topology and softness, [2,3] while modern electron microscopy methods, such as scanning electron microscopy (SEM) [4,5] and transmission electron microscopy (TEM), [6][7][8] can yield structural information even in the subnanometer range when there is sufficient electron density contrast. Despite the success of these methods, they are technically demanding and time-consuming. Furthermore, many softmatter samples possess poor electron contrast, and require non-invasive in situ imaging below the surface as well as the possibility to directly study dynamics. In recent years, superresolved fluorescence microscopy has revolutionized optical imaging, [9][10][11][12][13][14] by utilizing the photophysical or photochemical switching of fluorescent dyes in a sophisticated manner in combination with modern optics. So far, the life sciences have benefited, in particular, from the new possibilities of resolving structures well beyond the diffraction limit of light. Only a few examples of the application of super-resolution microscopy to materials science have been reported, [15][16][17][18] since concepts that require, for example, the addition of (polar) switching buffers often fail for these systems. Therefore, the main bottleneck for more universal applications of super-resolution imaging are switchable dyes with suitable (photo-)physical and chemical properties, such as high photostability, adjustable switching rates, minimum interaction with the environment to be probed, and simple design, with the possibility of multiple and straightforward derivatization for the specific labeling of structures or compartments. [19] ...

show abstract

mentioning

confidence: 85%

mentioning

confidence: 85%

Nanoscopic Visualization of Soft Matter Using Fluorescent Diarylethene Photoswitches

et al. 2016

View full text Add to dashboard Cite

show abstract

“…The photocyclization quantum yields F o-c of PMInDTEs were measured according to the literature method 24,25 (Supplementary Note 1 and Supplementary Table 4): proportion of parallel and anti-parallel conformation 19 . Therefore, the DTE in PMI-nDTEs system shows competitive ultraviolet sensitivity and contributes to the excellent fluorescence photoswitching performance.…”

Section: Resultsmentioning

confidence: 99%

A trident dithienylethene-perylenemonoimide dyad with super fluorescence switching speed and ratio

et al. 2014

View full text Add to dashboard Cite

Photoswitchable fluorescent diarylethenes are promising in molecular optical memory and photonic devices. However, the performance of current diarylethenes is far from satisfactory because of the scarcity of high-speed switching capability and large fluorescence on-off ratio. Here we report a trident perylenemonoimide dyad modified by triple dithienylethenes whose photochromic fluorescence quenching ratio at the photostationary state exceeds 10,000 and the fluorescence quenching efficiency is close to 100% within seconds of ultraviolet irradiation. The highly sensitive fluorescence on/off switching of the trident dyad enables recyclable fluorescence patterning and all-optical transistors. The prototype optical device based on the trident dyad enables the optical switching of incident light and conversion from incident light wavelength to transmitted light wavelength, which is all-optically controlled, reversible and wavelength-convertible. In addition, the trident dyad-staining block copolymer vesicles are observed via optical nanoimaging with a sub-100 nm resolution, portending a potential prospect of the dithienylethene dyad in super-resolution imaging.

show abstract

“…FLIM) and various modes for achieving spatial super-resolution. The latter effort has also involved the generation of suitable organic and nanoparticular probes [19,20].…”

Section: Discussionmentioning

confidence: 99%

Generation 3 programmable array microscope (PAM) for high speed large format optical sectioning in fluorescence

et al. 2015

Self Cite

View full text Add to dashboard Cite

We report on the current version of the optical sectioning programmable array microscope (PAM) implemented with a single digital micro-mirror device (DMD) spatial light modulator utilized as a mask in both the fluorescence excitation and emission paths. The PAM incorporates structured illumination and structured detection operating in synchrony. A sequence of binary patterns of excitation light in high definition format (19201080 elements) is projected into the focal plane of the microscope at the 18 kHz binary frame rate of the Texas Instruments 1080p DMD. The resulting fluorescent emission is captured as two distinct signals: conjugate (c, ca. "on-focus") consisting of light impinging on and deviated from the "on" elements of the DMD, and the non-conjugate (nc, ca. "out-of-focus") light falling on and deviated from the "off" elements. The two distinct, deflected beams are optically filtered and detected either by two individual cameras or captured as adjacent images on a single camera after traversing an image combiner. The sectioned image is gained from a subtraction of the nc image from the c image, weighted in accordance with the pattern(s) used for illumination and detection and the relative exposure times of the cameras. The widefield image is given by the sum of the c and nc images. This procedure allows a high duty cycle (typically 25-50%) of on-elements in the excitation patterns and thus functions with low light intensities, preventing saturation and minimizing photobleaching of sensitive fluorophores. The corresponding acquisition speed is also very high, limited only by the bandwidth of the camera(s) (100 fps full frame with the sCMOS camera in current use) and the optical power of the light source (lasers, large area LEDs). In contrast to the static patterns typical of SIM systems, the programmable array allows optimization of the patterns (duty cycle, feature size and distribution), thus enabling a wide range of applications, ranging from patterned photobleaching, (e.g., FRAP, FLIP) and photoactivation, spatial superresolution, automated adaptive tracking and minimization of light exposure (MLE), and photolithography.

show abstract

Photoswitchable fluorescent diheteroarylethenes: substituent effects on photochromic and solvatochromic properties

Cited by 41 publications

References 53 publications

Nanoscopic Visualization of Soft Matter Using Fluorescent Diarylethene Photoswitches

Nanoscopic Visualization of Soft Matter Using Fluorescent Diarylethene Photoswitches

A trident dithienylethene-perylenemonoimide dyad with super fluorescence switching speed and ratio

Generation 3 programmable array microscope (PAM) for high speed large format optical sectioning in fluorescence

Contact Info

Product

Resources

About