Fluorescent photochromes of diarylethene series: synthesis and properties

Ширинян, Валерий З.; Lonshakov, Dmitry V.; Lvov, Andrey G.; Krayushkin, M. M.

doi:10.1070/rc2013v082n06abeh004339

Cited by 42 publications

(11 citation statements)

References 189 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Upon switching off the irradiation source when the long-wavelength absorption exists, the intensity of spectral distribution remains constant during the observation period exceeding 3.6 × 10 3 s. Upon irradiation into the band characterized by the maximum at 546 nm, there is a fading and a full disappearance. Such behavior is typical for thermally stable products of diarylethene photocyclization. ,, …”

Section: Results and Discussionmentioning

confidence: 93%

“…The photochemical reactions of diarylethenes (stilbenes) with the participation of the hexatriene system are widely studied from the point of view of both theoretical and fundamental aspects and in terms of practical application. − The photochromic transformations of diarylethenes (reversible cyclization) attract researchers to design light-controlled materials and devices. − The most known reaction of the diarylethenes in synthetic chemistry is the photocyclization of hexatriene system followed by oxidation (Mallory reaction) or elimination. − These reactions find application in the synthesis of phenanthrene derivatives and are also extensively studied to develop effective methods for the synthesis of polyaromatic systems from simple compounds. Finally, in the past decade, a new reaction of diarylethene, a photocyclization with subsequent rearrangement resulting in the opening of one of the aromatic (in most cases, heterocyclic) rings, has been developed .…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Photochemical Rearrangement of Diarylethenes: Reaction Efficiency and Substituent Effects

et al. 2017

View full text Add to dashboard Cite

In recent years, great synthetic potential of the photorearrangement of diarylethenes leading to naphthalene derivatives via a cascade process of photocyclization/[1,n]-H shift/cycloreversion has been demonstrated. In this work, first a multifaceted study of the influence of various factors on the efficiency of the photorearrangement of diarylethenes of furanone series containing benzene and oxazole derivatives as aryl residues has been carried out. The efficiency of this phototransformation (quantum yields) and the effect of methoxy substituents in the phenyl moiety have been studied. Despite the multistage process, the quantum yields of the photorearrangement are rather high (0.34-0.49). It has been found that the efficiency of photocyclization of diarylethenes increases with the introduction of electron-donating methoxy groups in the phenyl moiety. Using the DFT calculations, we have been able to estimate in the photoinduced isomer the distance between hydrogen atom and carbon atom to which it migrates in the result of the sigmatropic shift. For all studied diarylethenes, this value was 2.67-2.73 Å, which is less than the sum of van der Waals radii of carbon and hydrogen atoms (2.9 Å).

show abstract

Section: Results and Discussionmentioning

confidence: 93%

Section: Introductionmentioning

confidence: 99%

Photochemical Rearrangement of Diarylethenes: Reaction Efficiency and Substituent Effects

et al. 2017

View full text Add to dashboard Cite

show abstract

“…Diarylethenes bearing two thiophene‐derived groups represent an interesting class of compounds nicely suitable for designing photoelectrochemical switches, Figure B. Numerous phototoswitchable derivatives have been synthesized for different applications . The photochromic features of these compounds are based on the reversible photoinduced transformations between their colorless unconjugated open‐ring and colored conjugated closed‐ring isomers under irradiation using a light source of appropriate wavelength, Figure A.…”

Section: Diarylethene‐based Photoelectrochemical Switchesmentioning

confidence: 99%

Modified Electrodes and Electrochemical Systems Switchable by Light Signals

Katz¹

2018

Electroanalysis

View full text Add to dashboard Cite

This article is an overview of extensive research efforts in many laboratories in the last two decades in the area of light‐switchable electrochemical systems and modified electrodes. Electrochemical reactions, including electrocatalytic and bioelectrocatalytic processes, have been reversibly activated and inhibited upon irradiation with light at different wavelengths. In order to realize these light activated or inhibited processes, the electrodes or/and reacting molecules were functionalized with photoisomerizable molecules including various derivatives of diarylethene, phenoxynaphthacenequinone, azobenzene and spiropyran/merocyanine. Photochemical reactions of these species resulted in change of their redox activity, conformation and electrical charge. All these changes affected electrode surfaces or (bio)molecules resulting in switching ON‐OFF corresponding (bio)electrochemical processes. Various systems based on different light‐controlled reactions are reviewed and discussed with specific examples and with many illustrating figures. Possible extensions of the research area and future applications are briefly overviewed in the conclusion section. The present comprehensive review is addressed to a broad scientific community, including newcomers to the area.

show abstract

“…Phototriggered functional materials, especially photochromic diarylethenes, have received tremendous research effort because of their distinctive molecular architectures and unique properties. , Since Irie and co-workers reported the first thermally irreversible photochromic diarylethene, a substituted cycloalkene bridged two aromatic heterocycle system with high fatigue resistance, plenty of such structures have been extensively investigated for their excellent properties and versatile applications in information storage, imaging devices, and molecular switches. − Especially, many dithienylethene assisted fluorophores have been designed for various fluorescent photoswitches, nondestructive readout, and chemical/biosensors. − However, most of them show significant fluorescence in solution but quenched in solid state or aggregate state, which limit their technological application, because many materials should be used in solid state or aggregate state. Conversely, tetraphenylethylene exhibits remarkable emission properties in solid state and aggregate state in contrast to near-quenching in solution because of the restriction of intramolecular rotation in solid state.…”

Section: Introductionmentioning

confidence: 99%

Hybrid cis/trans Tetra-arylethenes with Switchable Aggregation-Induced Emission (AIE) and Reversible Photochromism in the Solution, PMMA Film, Solid Powder, and Single Crystal

et al. 2017

View full text Add to dashboard Cite

How to efficiently design and synthesize multifunctional molecules is particularly challenging. In this presentation, we devote to constructing a kind of simple structures with composite functionalities through straightforward preparation. Starting from common commercially available materials, the titled cis/trans-tetraarylethenes can be conveniently obtained by a one-pot process under mild conditions. The different configurations were confirmed by H NMR and single crystal data analysis. The trans-tetraarylethenes could be converted into cis-forms not only by photoirradiation but also by microwave irradiation, which provided us a new choice for isomeric conversion, especially in relation to light sensitivity. Results show that all the hybrid cis/trans-isomers performed switchable fluorescence and reversible photochromism in solution, PMMA film, solid powder, and single crystal. Moreover, these hybrid tetraarylethenes could be utilized as photoswitchable media to tune the behavior of aggregation-induced emission (AIE) and aggregation-caused quenching (ACQ). These versatile properties are favorable for the potential applications in fluorescent photoswitches, nondestructive readout, and logic gates. We hope that our design strategy could provide a new protocol for constructing a kind of multifunctional molecules based some simple structure and convenient synthetic procedures.

show abstract

Fluorescent photochromes of diarylethene series: synthesis and properties

Cited by 42 publications

References 189 publications

Photochemical Rearrangement of Diarylethenes: Reaction Efficiency and Substituent Effects

Photochemical Rearrangement of Diarylethenes: Reaction Efficiency and Substituent Effects

Modified Electrodes and Electrochemical Systems Switchable by Light Signals

Hybrid cis/trans Tetra-arylethenes with Switchable Aggregation-Induced Emission (AIE) and Reversible Photochromism in the Solution, PMMA Film, Solid Powder, and Single Crystal

Contact Info

Product

Resources

About