Photochromism of Diarylethene Single Molecules in Polymer Matrices

Fukaminato, Tuyoshi; Umemoto, Tohru; Iwata, Yasuhide; Yokojima, Satoshi; Yoneyama, Mitsuru; Nakamura, Shinichiro; Irie, Masahiro

doi:10.1021/ja069131b

Cited by 157 publications

(111 citation statements)

References 49 publications

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“…The observed irreversibility could be the result of a strong association of DAE_Me (closed form) with the network of BTBT crystallites, thereby suppressing photoswitching of DAE_Me back into its open form. Similar phenomena have been observed previously where it was shown that the photochromism of DAEs is strongly dependent on their environment and arrangement in the solid [20][21][22] . An alternative explanation may be given considering the photochemically induced degradation of the DAEs, which on prolonged ultraviolet irradiation forms a by-product 23 (see below).…”

Section: Resultssupporting

confidence: 89%

Optically switchable transistors by simple incorporation of photochromic systems into small-molecule semiconducting matrices

et al. 2015

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The fabrication of multifunctional high-performance organic thin-film transistors as key elements in future logic circuits is a major research challenge. Here we demonstrate that a photoresponsive bi-functional field-effect transistor with carrier mobilities exceeding 0.2 cm 2 V À 1 s À 1 can be developed by incorporating photochromic molecules into an organic semiconductor matrix via a single-step solution processing deposition of a two components blend. Tuning the interactions between the photochromic diarylethene system and the organic semiconductor is achieved via ad-hoc side functionalization of the diarylethene. Thereby, a large-scale phase-segregation can be avoided and superior miscibility is provided, while retaining optimal p-p stacking to warrant efficient charge transport and to attenuate the effect of photoinduced switching on the extent of current modulation. This leads to enhanced electrical performance of transistors incorporating small conjugated molecules as compared with polymeric semiconductors. These findings are of interest for the development of high-performing optically gated electronic devices.

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Section: Resultssupporting

confidence: 89%

Optically switchable transistors by simple incorporation of photochromic systems into small-molecule semiconducting matrices

et al. 2015

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“…On the other hand, photochromic compounds establish a synthetic approach to design and develop efficient photoswitches. Photochromic materials have attracted considerable interest in the last decades as optoaddressable rewritable memory devices and reversible photoswitches [67][68][69][70][71][118][119][120][121][122][123]. Photochromism is defined as a reversible transformation of a molecule induced in one or both directions by absorption of electromagnetic radiation between two forms exhibiting different absorption spectra [124,125].…”

Section: Photochromic Conjugatesmentioning

confidence: 99%

“…Embedded in the hydrophobic cavities of water-soluble nanoparticles the mero form shows strong fluorescence with a maximum around 670 nm and a fluorescence quantum yield of 0.18 [137,138]. On the other hand, photochromic compounds can be used advantageously as fluorescence resonance energy transfer (FRET) acceptors to reversibly switch the fluorescence of a donor fluorophore [70,71,122,123,[137][138][139][140][141]. Switching of the donor fluorophore is performed by modulating the absorption properties of the photochromic compound (Fig.…”

Section: Photochromic Conjugatesmentioning

confidence: 99%

Photoswitches: Key molecules for subdiffraction‐resolution fluorescence imaging and molecular quantification

Heilemann

Dedecker

Hofkens

et al. 2009

Laser & Photonics Reviews

249

191

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Optical microscopes, often referred to as 'light microscopes', use visible light and a system of lenses to provide us with magnified images of small samples. Combined with highly sensitive fluorescence detection techniques and efficient fluorescent probes they allow the non-invasive 3D study of subcellular structures even in living cells or tissue. However, optical microscopes are subject to the diffraction barrier of light which imposes an optical resolution limit of approximately 200 nm in the imaging plane. In the recent past new techniques emerged that break the diffraction barrier and enable structural investigations with so far unmatched resolution. They are all based on the selective switching of fluorophores between a fluorescent and a nonfluorescent state and are therefore generalized under the denotation "Photoswitching Microscopy". Here we review recent progress in subdiffraction-resolution fluorescence imaging microscopy using various photoswitchable fluorophores and strategies. Special emphasis will be placed on the design and development of photoswitches and the requirements photoswitches have to fulfill for successful use in photoswitching microscopy. Moreover, we demonstrate how photoswitches can be used advantageously for molecular quantification, i.e. the determination of densities and absolute numbers of proteins located in specific subcellular compartments and discuss concepts how standard organic fluorophores can be used successfully for photoswitching microscopy.All subdiffraction-resolution fluorescence imaging methods are based on the separation of fluorescence emission in time. Thus, they critically depend on the availability of photoswitches, i.e. molecules that can be switched between a fluorescent and nonfluorescent state upon irradiation with light with high reliability. Here we describe the development and operation methods of diverse photoswitches and their application for superresolution fluorescence imaging and molecular quantification.

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“…Although the single-molecule approach provides detailed information about the properties and mechanisms, only a few examples of fluorescent switches have been demonstrated (4,5). Among the fluorescent switches, there are systems that use 2 different wavelengths for switching (photoswitchable molecules) (6)(7)(8)(9)(10)(11)(12)(13), those that switch the efficiency of photoinduced electron transfer (14,15) and those that respond to pH changes (15,16).…”

mentioning

confidence: 99%

Controlling the fluorescence of ordinary oxazine dyes for single-molecule switching and superresolution microscopy

Vogelsang

Cordes

Forthmann

et al. 2009

Proc. Natl. Acad. Sci. U.S.A.

257

331

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Fluorescent molecular switches have widespread potential for use as sensors, material applications in electro-optical data storages and displays, and superresolution fluorescence microscopy. We demonstrate that adjustment of fluorophore properties and environmental conditions allows the use of ordinary fluorescent dyes as efficient single-molecule switches that report sensitively on their local redox condition. Adding or removing reductant or oxidant, switches the fluorescence of oxazine dyes between stable fluorescent and nonfluorescent states. At low oxygen concentrations, the off-state that we ascribe to a radical anion is thermally stable with a lifetime in the minutes range. The molecular switches show a remarkable reliability with intriguing fatigue resistance at the single-molecule level: Depending on the switching rate, between 400 and 3,000 switching cycles are observed before irreversible photodestruction occurs. A detailed picture of the underlying photoinduced and redox reactions is elaborated. In the presence of both reductant and oxidant, continuous switching is manifested by ''blinking'' with independently controllable on-and off-state lifetimes in both deoxygenated and oxygenated environments. This ''continuous switching mode'' is advantageously used for imaging actin filament and actin filament bundles in fixed cells with subdiffraction-limited resolution.electron transfer ͉ molecular switch ͉ sensor ͉ single-molecule spectroscopy M olecular switches are single-molecule devices, and hence they are key building-blocks for future, bottom-up nanotechnological devices in computers, data storages, (bio-) sensors, and displays. Furthermore, they are exciting molecules for triggered drug-release or for superresolution imaging (1-3). Molecular switches possess at least 2 stable states and can be converted between these states by external stimuli. These external stimuli can essentially be any kind of physical or chemical trigger, such as light, electricity, or certain chemical reactions. Fluorescence is a preferred transduction mechanism because of its ease of noninvasive detection with ultimate sensitivity (i.e., single-molecule sensitivity). For future devices and for superresolution microscopy, it is also important that the molecular switches can be operated at the level of single molecules. This requirement imposes further demands with respect to reliability, reproducibility, response time, and fatigue resistance. Although the single-molecule approach provides detailed information about the properties and mechanisms, only a few examples of fluorescent switches have been demonstrated (4, 5). Among the fluorescent switches, there are systems that use 2 different wavelengths for switching (photoswitchable molecules) (6-13), those that switch the efficiency of photoinduced electron transfer (14, 15) and those that respond to pH changes (15,16).Here, we show that based on a detailed understanding of their photophysics, ordinary, fluorescent dyes can act as single-molecule switches and sensors. By adapting...

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Photochromism of Diarylethene Single Molecules in Polymer Matrices

Cited by 157 publications

References 49 publications

Optically switchable transistors by simple incorporation of photochromic systems into small-molecule semiconducting matrices

Optically switchable transistors by simple incorporation of photochromic systems into small-molecule semiconducting matrices

Photoswitches: Key molecules for subdiffraction‐resolution fluorescence imaging and molecular quantification

Controlling the fluorescence of ordinary oxazine dyes for single-molecule switching and superresolution microscopy

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