Esterifiable/hydrolytic control of photochromism of diarylethenes with 8-hydroxyquinoline derivatives

Song, Bo; Li, Haixia; Lin, Yanli; Zhao, Chunlin; Sai, Huazheng; Zhang, Shiman; Zhang, Fushi; Xiang, Jinjuan

doi:10.1016/j.jphotochem.2012.05.005

Cited by 7 publications

(6 citation statements)

References 33 publications

(31 reference statements)

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“…Diarylethenes That Undergo Electrochemical Cyclization and Cycloreversion Reactions [194][195][196][197]199 Several photochromic diarylethene derivatives, the reactivity of which is controlled by the addition of acid or base, have been reported. [240][241][242][243][244][245][246]250 Although diarylethene 127, in which (4pyridyl)ethynyl units are attached to the 6π-electron hexatriene moiety, undergoes a normal photochromic reaction in CH 2 Cl 2 , the photochromic reactivity is strongly suppressed upon quaternarization of the pyridine moieties in any solvent. 240 The gated photoreactivity is locked by the addition of trifluoroacetic acid and unlocked by diethylamine.…”

Section: Gated Reactivitymentioning

confidence: 99%

“…Gated photochromic reactivity is the property that additional external stimuli, such as another photons, chemicals, or heat, can control the photochromic reactions. Various approaches to attain the gated reactivity have been proposed. − ,− ,− …”

Section: Propertiesmentioning

confidence: 99%

“…Several gated reaction systems based on chemical stimuli have been developed to manipulate the photochromic reactivity, as listed in Table . − Maleimide-type diarylethene derivatives having a N -( O -hydroxyphenyl) group 119 and 120 were designed and synthesized to introduce chemically gated reactivity . These derivatives are photochemically inactive because excited states of the molecules are efficiently quenched by an intramolecular proton transfer.…”

Section: Propertiesmentioning

confidence: 99%

“…Several photochromic diarylethene derivatives, the reactivity of which is controlled by the addition of acid or base, have been reported. − , Although diarylethene 127 , in which (4-pyridyl)ethynyl units are attached to the 6π-electron hexatriene moiety, undergoes a normal photochromic reaction in CH 2 Cl 2 , the photochromic reactivity is strongly suppressed upon quaternarization of the pyridine moieties in any solvent . The gated photoreactivity is locked by the addition of trifluoroacetic acid and unlocked by diethylamine.…”

Section: Propertiesmentioning

confidence: 99%

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Photochromism of Diarylethene Molecules and Crystals: Memories, Switches, and Actuators

et al. 2014

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Section: Gated Reactivitymentioning

confidence: 99%

Section: Propertiesmentioning

confidence: 99%

Section: Propertiesmentioning

confidence: 99%

Section: Propertiesmentioning

confidence: 99%

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Photochromism of Diarylethene Molecules and Crystals: Memories, Switches, and Actuators

et al. 2014

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“…Several attempts to modulate the photochromic properties of diarylethenes for practical applications have recently been reported. [7][8][9][10][11][12][13][14][15][16][17][18][19] Recently, it was found that the photochromic properties of some organic molecules can be induced by an external stimulus such as chemicals, [20][21][22] heat 23 or oxidation/reduction. 24 For instance, Irie 20 reported that photochemically inactive diarylethene derivatives having a N-(O-hydroxyphenyl) group underwent a photochromic reaction when they were esterified by the addition of acetic anhydride.…”

Section: Introductionmentioning

confidence: 99%

Chemical control of photochromism and a multiresponsive molecular switch based on a diarylethene derivative containing naphthol

Liu

et al. 2014

Photochem Photobiol Sci

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A photochemically inactive diarylethene derivative with a naphthol group bridging through the imidazole unit (DIN) was synthesized to characterize a multifunctional switch. Upon stimulation by radiation (UV and visible light), the target diarylethene derivative DIN was not photochemically inactive but photo-active, it could be photo-converted into a keto compound. Moreover, the photochromic reaction of DIN was observed when it was stimulated by the addition of acid or methylation. Fluorescence quenching and the bathochromic effect occurred when DIN was stimulated by the addition of copper ions and a base, respectively. Its optical properties could be regulated by various chemical stimuli. Thus, it can potentially be utilized as a multiresponsive molecular switch.

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Future‐Oriented Advanced Diarylethene Photoswitches: From Molecular Design to Spontaneous Assembly Systems

et al. 2022

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cycloreversion of DAE under light irradiation produces many exciting functional effects, such as changes in photophysical and photochemical properties, [12] changes in the shape or mechanical properties of the solid, [13] electrical conductivity, [7b,14] and the generation of reactive oxygen species (ROS). [15] This type of photochromic compound can be considered a stilbene derivative. At this time, the most widely known and systematically studied DAE derivative structure contains two aryl groups and a benzene ring (usually two identical or different thiophene units with low aromatic stabilization energy [16] ) and a five-membered ring of perfluorocyclopentene and cyclopentene units [17] where the ethene bridge is located, which significantly improve photochromism. [18] In essence, the DAE photoisomerization process is a reversible electrocyclic reaction of the central 6π-electron systems. [2] Under light irradiation, DAE can rapidly and reversibly transform between its open and closed forms, and that transformation is accompanied by a color change caused by a change in the π-conjugation distribution. [2] The important thing is that the colorless opened-and colored closed-ring isomers are both thermally stable; that is, cyclization and cycloreversion do not proceed spontaneously in the dark; they need to be driven by external light irradiation at specific wavelengths. [2,19] Compared with classic lightresponsive molecules such as azobenzene, [20] the light intensity required to drive the isomerization of DAE is relatively low. Moreover, even after multiple cycles, the photochromic performance does not show significant fatigue in either the solution or solid state. [2,18b,21] DAE research to this point can be roughly divided into three stages in chronological order: early exploration of DAE's molecular structure and theory, nearly two decades of purpose-oriented molecular structure modification research, and about ten years of research into practical applications of DAE in assembly systems. Research before about 2000 focused mainly on developing more abundant DAE-derivative structures and advancing the systematic understanding of DAE's physical and chemical properties and switching performance. To regulate its switching performance and give it new functionality, many strategies for modifying the ethene bridge and aryl groups of DAE have been proposed. [22] In the first two research stages, the mechanisms and structural modification of DAE isomerization were thoroughly and systematically explored, and countless important Diarylethene (DAE) photoswitch is a new and promising family of photochromic molecules and has shown superior performance as a smart trigger in stimulus-responsive materials. During the past few decades, the DAE family has achieved a leap from simple molecules to functional molecules and developed toward validity as a universal switching building block. In recent years, the introduction of DAE into an assembly system has been an attractive strategy that enables the photochromic behavior of the b...

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Esterifiable/hydrolytic control of photochromism of diarylethenes with 8-hydroxyquinoline derivatives

Cited by 7 publications

References 33 publications

Photochromism of Diarylethene Molecules and Crystals: Memories, Switches, and Actuators

Photochromism of Diarylethene Molecules and Crystals: Memories, Switches, and Actuators

Chemical control of photochromism and a multiresponsive molecular switch based on a diarylethene derivative containing naphthol

Future‐Oriented Advanced Diarylethene Photoswitches: From Molecular Design to Spontaneous Assembly Systems

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