Extraordinarily High Thermal Stability of the Closed-ring Isomer of 1,2-Bis(5-methyl-2-phenylthiazol-4-yl)perfluorocyclopentene

Takami, Shizuka; Kobatake, Seiya; Kawai, Tsuyoshi; Irie, Masahiro

doi:10.1246/cl.2003.892

Cited by 69 publications

(41 citation statements)

References 12 publications

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“…These values were very similar to those of perfluorocyclopentene derivatives 2 o and 2 c ( 2 o : λ max : 300 nm ( ϵ : 3.4×10 4 m −1 cm −1 ), 2 c : λ max : 525 nm ( ϵ : 1.0×10 4 m −1 cm −1 ), 0.32 ( Φ oc at 313 nm) and 0.02 ( Φ co at 492 nm)) in hexane. Additionally, 1 c showed much better thermal stability compared with that of 2 c , the half‐life of which is reported to be 30 h at 180 °C in degassed decalin. In contrast, the half‐life of 1 c was almost 80 h at the same temperature in decalin under the same conditions (Figure S1 in the Supporting Information).…”

Section: Methodsmentioning

confidence: 98%

Photosalient Effect of a Diarylethene with a Perfluorocyclohexene Ring

Hatano

Morimoto

Hyodo

et al. 2016

Chemistry A European J

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Crystals of a diarylethene with a perfluorocyclohexene ring exhibit a remarkable photosalient effect upon UV light irradiation that is attributed to the structural changes that occur when going from open- to closed-ring isomers in the crystalline state, together with the existence of two conformers with different photoconversions compared with those of a perfluorocyclopentene derivative. Our current results give a design principle for molecular structures so as to achieve the photosalient effect for photochromic crystals.

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Section: Methodsmentioning

confidence: 98%

Photosalient Effect of a Diarylethene with a Perfluorocyclohexene Ring

Hatano

Morimoto

Hyodo

et al. 2016

Chemistry A European J

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“…• C [71,133,134]. Diarylethene derivatives with fivemembered heterocyclic rings have two conformations with the two rings in mirror symmetry (parallel conformation) and in C 2 symmetry (antiparallel conformation) [68].…”

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

248

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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“…This observation indicated the presence of a steric contact between the morpholine fragment and aromatic substituent also in the case of hydrolyzed derivatives 10a,b,d. In the case of spiranes 10a,b,d, 13 С NMR signals had similar chemical shifts to the respective 13 С NMR signals of compounds 4b, indicating the preservation of carbon atom skeleton during the treatment of imines 4 with hydrochloric acid.…”

mentioning

confidence: 68%

“…8 The potential for practical applications of DAE in the indicated areas motivate synthetic studies of photochromes with precisely designed photophysical parameters, such as thermal stability of the photoinduced form, [9][10][11][12][13][14][15] quantum yield of the forward and reverse photoreaction, [16][17][18][19][20] and the phototransformation cyclicity. [21][22][23][24] An important direction of study, with the goal of improving the practical characteristics of DAE, is the development of synthetic methods for obtaining DAE with intramolecular noncovalent interactions and steric hindrance.…”

mentioning

confidence: 99%

Directed synthesis of new spiro-fused photochromes of diarylethene series

Belikov

Ievlev

Belikova

et al. 2015

Chem Heterocycl Comp

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518Diarylethenes (DAE, dihetarylethenes) are subject to intense study due to the possibility of using these compounds as photosensitive components in various applications, in particular, information processing, 1-4 optical switches for organic electronics, 5-7 and biosensors. 8 The potential for practical applications of DAE in the indicated areas motivate synthetic studies of photochromes with precisely designed photophysical parameters, such as thermal stability of the photoinduced form, 9-15 quantum yield of the forward and reverse photoreaction, 16-20 and the phototransformation cyclicity. 21-24 An important direction of study, with the goal of improving the practical characteristics of DAE, is the development of synthetic methods for obtaining DAE with intramolecular noncovalent interactions and steric hindrance. 25-31 One of the methods for creating a non-covalent interaction in DAE is the introduction of spiro-fused structures at the ethene linker. We should note that only isolated examples of spirofused DAE are known. 31-33 However, based on the current data, it is expected that the presence of spiro-fused moiety at the ethene linker could be used to confer certain useful properties to DAE. For example, some of the best forward quantum reaction yields have been demonstrated for spirofused DAE specifically due to the non-covalent interaction, caused by the presence of spirofusion. 31 By introducing or removing spirofusion it may be possible to tune the ability of DAE to undergo photochromic transformations. 32 The introduction of spirofusion may also be used for the preparation of DAE with several photoswitchable fragments. 33 The presented data show the importance of developing new approaches to the synthesis of diarylethenes featuring a rare combination of structural moieties, in particular spiro-fused systems. With this in mind, we set out to expand the range of available methods for the synthesis of DAE with spirofusion at the ethene linker.Recently we demonstrated a new approach to the synthesis of photochromic DAE, based on the transformations of intermediates obtained by reactions of tetracyanoethylene (TCNE) with 1,2-diarylethanones, namely, 3,4-diaryl-4-oxobutane-1,1,2,2-tetracarbonitriles. 34 At the same time, it is known that 4-oxoalkane-1,1,2,2-tetracarbonitriles based on some aliphatic and alkylaromatic ketones react with amines forming spiro compounds, containing an The reaction of tetracyanoethylated 1,2-diarylethanones with morpholine was used for directed synthesis of spiro-fused diarylethenes, 8-amino-1-imino(oxo)-6-morpholino-2-oxa-7-azaspiro[4.4]nona-3,6,8-triene-9-carbonitriles. The intermediates in this process were tetracyanoalkanone salts. The formation of spiranes was sensitive to the nature of aromatic substituents at the carbonyl group of 3,4-diaryl-4-oxobutane-1,1,2,2-tetracarbonitriles. The obtained spiro-fused diarylethenes exhibited photochromic properties.

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Extraordinarily High Thermal Stability of the Closed-ring Isomer of 1,2-Bis(5-methyl-2-phenylthiazol-4-yl)perfluorocyclopentene

Cited by 69 publications

References 12 publications

Photosalient Effect of a Diarylethene with a Perfluorocyclohexene Ring

Photosalient Effect of a Diarylethene with a Perfluorocyclohexene Ring

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

Directed synthesis of new spiro-fused photochromes of diarylethene series

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