Diarylethene 1o Research Articles

A New High Selective and Sensitive Fluorescent Probe for Al3+ based on Photochromic Salicylaldehyde Hydrazyl Diarylethene.

A new diarylethene derivative 1O decorated with a salicylaldehyde hydrazine moiety was designed and synthesized successfully, and its structure was confirmed by NMR. Diarylethene 1O showed eminent photochromism and high selectivity and sensitivity for Al3+ with turn-on fluorescent performance. As the concentration of Al3+ in 1O solution increased, the color of solution remarkably changed from dark to bright green with 313-fold fluorescent emission intensity enhancement. The 1:1 combination stoichiometry between 1O and Al3+ was verified by Job's plot and MS analysis. The association constant between 1O and Al3+ was 3.9 × 102mol-1 L, and the limit of detection toward Al3+ was 7.98 × 10-9mol L-1. Meanwhile, the probe can be utilized in practical water and logic circuits.

A novel diarylethene probe with high selective recognition of CN- and Mg2+and its application

A chemical sensor composed of pyridoxal hydrochloride schiff base based on diarylethene (1O) was synthesized. Its photochemical properties and selectivity to ions were further studied. The chemosensor could detect cyanide effectively and is almost undisturbed by other ions. When titrating CN−, the reaction aroused a distinct change in the absorption spectrum with the color change from transparent to yellow, and the fluorescence intensity centered at 562 nm was increased 68 folds. It also exhibited a good fluorescence sensing of Mg2+ with high selectivity and sensitivity. Upon addition of Mg2+, its emission intensity enhanced 110 folds, with the color change from dark to bright blue. Its good spectral response could be applied to molecular logic circuit. Moreover, the chemosensor could be made into test paper strips for the qualitative and quantitative detection of CN− and Mg2+.

A new fluorescence sensor based on diarylethene with a N'-(quinolin-8-ylmethylene)benzohydrazide group for Zn2+ detection

A novel photochromic diarylethene 1O composed of a N'-(quinolin-8-ylmethylene)benzohydrazide group as the binding unit for metal ions and perfluorodiarylethene as a photoswitching trigger has been designed and synthesized. 1O exhibited sensitivity to light irradiation and Zn2+. Stimulated by UV/Vis light and Zn2+, distinct changes were observed in the UV–vis and fluorescence spectra. The binding of Zn2+ caused the open-ring absorption band of 1O to display an intense absorption band at 412 nm with a notable color change from colorless to yellow. Furthermore, Zn2+ induced a fluorescence “turn-on” of 1400-fold and a fluorescence color change form dark to bright green due to the chelation-enhanced fluorescence effect. A Job’s plot established the 1:1 stoichiometry of the complex formation between 1O and Zn2+, and the limit of detection for Zn2+ is as low as 3.2 × 10–8 mol L–1. Therefore, the compound could be used as a selective and sensitive fluorescence ratiometric sensor for the detection of Zn2+. Finally, we demonstrated that the sensor can penetrate into HeLa cells and could be used for the determination of intracellular Zn2+.

A new diarylethene-derived probe for colorimetric sensing of Cu(II) and fluorometric sensing of Cu(II) and Zn(II): Photochromism and High Selectivity

A novel photochromic diarylethene derivative containing a 2-(methylthio)benzenamine Schiff base (1O) unit was synthesized and its selective fluorometric/colorimetric sensing of multiple metal ions in methanol was demonstrated. The addition of Cu2+ enhanced the absorption of 1O up to 44 folds with the concomitant color change from colorless to yellow, which could be easily observed by the naked eye. In addition, 1O exhibited selective fluorescence responses to Cu2+ and Zn2+ with different fluorescence signals. Cu2+ quenched the fluorescence of 1O up to 98%, while Zn2+ enhanced the fluorescence of 1O by 53.8 folds, accompanied by the fluorescence color changes from light red to dark and bright yellow, respectively. Both coordination stoichiometries between 1O and Cu2+, and 1O and Zn2+ were determined to be 1:1. In all, diarylethene 1O can be potentially used as a chemosensor of both Cu2+ and Zn2+.

Synthesis and Photochromic Properties of Diarylethene 1-[2-methyl-5- phenyl-3-thienyl]-2-[2-methyl-5-(4-benzoicacid)-3-thienyl] Perfluorocyclopentene

An unsymmetrical photochromic diarylethene 1O, 1-[2-methyl-5- phenyl-3- thienyl]-2- [2-methyl-5-(4-benzoicacid)-3-thienyl] perfluorocyclopentene was constructed, and its photochromic properties, fatigue resistance, kinetics of the photochromic cyclization/ cycloreversion and fluorescence were examined in detail. The results suggested that its photochromic behavior could be modulated by UV/Vis light, accompanied by the color change from colorless to blue. Ten coloration-decoloration cycles of 1O caused only 8.7 % degradation.

Synthesis and Photochromism Studies of 1‐(2‐methyl‐3‐benzoth iophenyl)‐2‐[2‐methyl‐5‐(4‐bromomethylphenyl)‐3‐thienyl] perfluorocyclopentene

An unsymmetrical photochromic diarylethene was synthesized and its photochromism and fluorescent properties were investigated in detail. The results showed that this compound exhibited reversible photochromism, changing from colorless to purple after irradiation with UV light in solution. Diarylethene 1o also exhibited obviously fluorescence switch property. What is more, the kinetic experiments illustrated that the cyclization/cycloreversion process of this compound was determined to be the zeroth/first reaction.

Synthesis and Properties of 1-(3,5-Dimethyl-4-isoxazolyl)-2- [2-methyl-5-(3-fluoro-4-chloro)phenyl-3- thienyl]perfluorocyclopentene

An asymmetrical photochromic diarylethene 1-(3,5-Dimethyl-4-isoxazolyl)-2-[2- methyl-5-(3-fluoro-4-chloro)phenyl-3-thienyl]perfluorocyclopentene (1o) was synthesized and its photochromic properties were investigated. Upon irradiation with 297 nm UV light, diarylethene 1o exhibited photochromism in solution and in PMMA film. Moreover, 1o also exhibited obviously fluorescence switches along with the photochromism.

Synthesis and Photochromism studies of 1-(2-methyl-3- benzothiophene)-2-[2-methyl-5-pyrenyl-3-thienyl] perfluorocyclopentene

A new unsymmetrical photochromic diarylethene 1o, which contains condensed nucleus was synthesized. Its photochromic both in hexane solution and in PMMA film and kinetics experiment were investigated in detail. The result indicated that this diarylethene had reversible photochromism, changing the color from colorless to purple both in hexane solution and in PMMA film upon appropriate irradiation with 297 nm UV light. What’s more, the kinetic experiments showed that the cyclization and cycloreversion processes were zeroth and first order reaction, respectively. This new photochromic system also exhibited fluorescence switching in hexane solution and in PMMA film.

Highly selective ratiometric fluorescent Zn2+ chemosensor based on diarylethene derivative with bi-8-carboxamidoquinoline unit.

An asymmetrical diarylethene (1O) with a bi-8-carboxamidoquinoline unit was synthesized. Its photochromic and fluorescence performances on stimulation with both light and metal ions showed that the diarylethene could serve as a highly selective ratiometric fluorescent chemosensor to detect Zn2+ ions based on internal charge transfer and chelation-enhanced fluorescence processes. The diarylethene could selectively discriminate Zn2+ from Cd2+ in acetonitrile. Furthermore, Job's plots based on fluorescence titration and electrospray ionization mass spectrometry analysis showed 1 : 1 binding stoichiometry between 1O and Zn2+ . The binding constant of 1O with Zn2+ , estimated using the Benesi-Hildebrand method, and the limit of detection were 3.37 × 105 M-1 and 4.6 × 10-8 mol/L, respectively. Additionally, the light and metal-responsive fluorescence behavior of 1O was used successfully to construct a molecular logic circuit with four inputs and one output. Copyright © 2016 John Wiley & Sons, Ltd.

Synthesis and Properties of 1-(2-Methyl-3-benzothiophene)-2-[2-methyl-5-(3-fluoro-4-chloro)phenyl-3-thienyl]perfluorocyclopentene

An asymmetrical photochromic diarylethene1-(2-Methyl-3-benzothiophene)-2-[2-methyl-5-(3-fluoro-4-chloro) phenyl-3-thienyl] perfluorocyclopentene (1o) was synthesized and its phtochromic, fluorescent properties were investigated in detail. This compound exhibited remarkable photochromism, upon irradiation with 297 nm UV light, the colorless solution of 1o turned to violetred with a new visible absorption band centered at 538 nm (ε = 1.17 × 104 L mol-1 cm-1) attributable to the closed-ring isomer 1c. The kinetic experiments showed that the cyclization and cycloreversion processes were zeroth and first order reaction, respectively. Moreover, diarylethene 1o also exhibited obviously fluorescence switches along with the photochromism.The emission intensity of diarylethene 1o in a photostationary state was quenched to ca. 27% in hexane.

Synthesis and Photochromism Studies of 1,2-bis[2-methyl-5-(4-bromomethylphenyl)-3-thienyl] Perfluorocyclopentene

A symmetrical photochromic diarylethene was synthesized, and its optoelectronic properties were also investigated. The results showed that this compound exhibited reversible photochromism, changing from colorless to blue after irradiation with UV light in solution. The open-ring isomer of the diarylethene 1o exhibited relatively strong fluorescence at 477 nm in acetonitrile solution (2×10-5 mol L-1) when excited at 325 nm. The fluorescence intensity decreased along with the photochromism upon irradiation with 297 nm light. What is more, the kinetic experiments illustrated that the cyclization/cycloreversion process of this compound was determined to be the zeroth/first reaction. In addition, the results demonstrated that the diarylethene 1o had remarkable photochromic properties.

Synthesis and Properties of 1-(2-Cyano-1,5-Dimethyl-4-Pyrryl)-2-{2-Methyl-[5-(4-Methylene-Hydroxyl)Phenyl]-3-Thienyl}Perfluorocyclopentene

A new asymmetrical photochromic diarylethene 1-(2-cyano-1,5-dimethyl-4-pyrryl)-2-{2-methyl-[5-(4-methylene-hydroxyl) phenyl]-3-thienyl} perflu-orocyclopentene (1o) was synthesized and its photochromic properties were investigated systematically. Upon irradiation with 297 nm UV light, 1o exhibited photochromism in acetonitrile solution and in a PMMA amorphous film. The kinetic experiments showed that the cyclization and cycloreversion processes were zeroth and first order reaction, respectively. In addition, diarylethene 1o also exhibited obvious fluorescence switches along with the photochromism.

Synthesis and Properties of 1,2-Bis[2-Methyl-5-(9,9-Dihexyl-Fluorene)-3-Thienyl]Perfluorocyclopentene

A new symmetrical photochromic diarylethene 1,2-bis [2-methyl-5-(9,9-dihexyl-fluorene)-3-thienyl] perfluorocyclopentene (1o) has been synthesized, and its optoelectronic properties, such as photochromism and the fluorescence spectra of diarylethene 1o in acetonitrile solution was investigated. The maxima absorption of compound closed-ring isomer 1c is 619 nm. The open-ring isomer of the diarylethene 1o exhibited fluorescence at 390 nm. Its fluorescence intensity decreased along with the photochromism from open-ring isomers to closed-ring isomers upon irradiation with 297 nm UV light,The results showed that this compound exhibited reversible photochromism and fluorescent switching in solution after irradiation with UV light and visible light.

Research on Photochromic Materials with Synthesis and Properties of 1-(2-Methyl-3-Benzothiophene)-2-[2-Methyl-5-(3-Cyanophenyl)-3-Thienyl]Perfluorocyclopentene

An asymmetrical photochromic diarylethene1-(2-Methyl-3-benzothiophene)-2-[2-methyl-5-(3-cyanophenyl)-3-thienyl] perfluorocyclopentene (1o) was synthesized and its phtochromic, fluorescent properties in both solution and PMMA films were investigated in detail. This compound exhibited remarkable photochromism, upon irradiation with 297 nm UV light, the colorless solution of 1o turned to violet with a new visible absorption band centered at 535 nm (ε = 1.08 × 104 L mol-1 cm-1) attributable to the closed-ring isomer 1c. The emission intensity of diarylethene 1o in a photostationary state was quenched to ca. 32% in hexane and 43% in PMMA film.

Research on Photochromic Materials with Synthesis and Properties of 1-(3,5-Dimethyl-4-isoxazolyl)-2-[2-methyl-5-(<i>p</i>-ethoxyphenyl)-3-thienyl]perfluorocyclopentene

An asymmetrical photochromic diarylethene 1-(3,5-Dimethyl-4-isoxazolyl)-2-[2-methyl-5-(p-ethoxyphenyl)-3-thienyl] perfluorocyclopentene (1o) was synthesized and its photochromic properties were investigated. Upon irradiation with 297 nm UV light, 1o exhibited photochromism in hexane solution. The kinetic experiments showed that the cyclization and cycloreversion processes were zeroth and first order reaction, respectively. Moreover, diarylethene 1o also exhibited obviously fluorescence switches along with the photochromism.

Research on Photochromic Materials with Synthesis and Application of 1-(2-methyl-3-benzothienyl)-2-[2-methyl-(5-ethynyl)trimethylsilane-3-thienyl] Perfluorocyclopentene

A new unsymmetrical photochromic diarylethene compound, 1-(2-methyl-3-benzothienyl)-2-(2-methyl-(5-ethynyl) trimethylsilane-3-thienyl) perfluorocyclopentene (1o) has been synthesized, and its optoelectronic properties, such as photochromism and the fluorescence spectra of diarylethene 1o in hexane solution was investigated. The results showed that this compound exhibited reversible photochromism in solution. The maxima absorption of compound closed-ring isomer 1c are 538 nm. Its fluorescence intensity decreased along with the photochromism from open-ring isomers to closed-ring isomers upon irradiation with 297 nm UV light.

Synthesis and Properties of 1-(2,4-Dimethyl-5-thiazolyl)-2-(2-methyl-5-(2-methyl)-3-thienyl)perfluorocyclopentene

An asymmetrical photochromic diarylethene 1-(2,4-dimethyl-5-thiazolyl)-2-(2-methyl-5-(2-methyl)-3-thienyl) perfluorocyclopentene (1o) was synthesized and its photochromic properties were investigated. Upon irradiation with 297 nm UV light, 1o exhibited photochromism in solution and in PMMA film. The kinetic experiments showed that the cyclization and cycloreversion processes were zeroth and first order reaction, respectively. Moreover, diarylethene 1o also exhibited obviously fluorescence switches along with the photochromism.

Synthesis and Photochromic Properties of 1-(2-methyl-1-phenyl)-2-[2-methyl-5-(4-formylphenyl)-3-thienyl]perfluoroyclopentene

An unsymmetrical photochromic diarylethene 1-(2-methyl-1-phenyl)-2-[2-methyl-5-(4-formylphenyl)-3-thienyperfluoroyclopentene (1o) was designed and constructed successfully. Its photochromic properties were examined. The results showed that the compound exhibits good photochromism with UV/Vis light irradiation. The diarylethene 1o changed the color from colorless to blueviolet upon irradiation with 297 nm UV light, in which absorption maxima were observed at 549 and 581nm in hexane and PMMA films, respectively.The photochromic cyclization/cycloreversion kinetics of 1o in hexane were determined by UV-Vis spectra upon alternating irradiation with UV and appropriate wavelength visible light.

Synthesis and Properties of [1-(2-Methyl-5-pheyl-3-thienyl)-2-(2-methyl-5-(4-cyanophenyl)-3-thienyl]perfluorocyclopentene for Fluorescence Switch

A novel unsymmetrical photochromic diarylethene 1o, which is named [1-(2-Methyl-5-pheyl-3-thienyl)-2-(2-methyl-5-(4-cyanophenyl)-3-thienyperfluorocyclopentene, was synthesized and its structure authenticated. What is more, photochromic, kinetics and fluorescence properties of the diarylethene were investigated in detail. The result indicated that this diarylethene photochromism could be controlled by UV-Vis light, changing the color from colorless to blue in hexane solution upon appropriate irradiation with 297 nm light, respectively. Its In the meantime, the kinetic experiments illustrated that the cyclization/cycloreversion process of this compound was determined to be the zeroth/first reaction. In addition, the fluorescence intensity of diarylethene decreased dramatically from open-ring isomer to closed-ring isomer. The fluorescence switching property can be potential use for optical data storage.

Synthesis and Photochromism Studies of 1-(2-Methyl-3-Benzothiophenyl)-2-[2-Methyl-5-(4-Azidomethyl)-3-Thienyl]Perfluorocyclopentene

An unsymmetrical photochromic diarylethene 1-(2-methyl-3-benzothiophenyl)-2-[2-methyl-5-(4-azidomethyl)-3-thienyperfluorocyclopentene was synthesized, and its optoelectronic properties were also investigated. The results showed that this compound exhibited reversible photochromism, changing from colorless to darkorange after irradiation with UV light in solution. The open-ring isomer of the diarylethene 1o exhibited relatively strong fluorescence at 457 nm in acetonitrile solution (2×10-5 mol L-1) when excited at 287 nm. The fluorescence intensity decreased along with the photochromism upon irradiation with 297 nm light. The electrochemical properties indicated that the oxidation onset and the Eg of the open-ring isomer were lower than the closed-ring isomer.