Photochromism of a New Unsymmetrical Diarylethene Bearing both Thiazole and a Methoxyl Group

2011 ◽  
Vol 295-297 ◽  
pp. 228-231
Author(s):  
Hui Li ◽  
Shou Zhi Pu ◽  
Shi Qiang Cui

A new unsymmetrical isomeric diarylethene bearing an electron-donating methoxyl group atortho-positions of the terminal phenyl ring was synthesized, namely 1-(2,4-dimethyl-5-thiazolyl) -2-[2-methyl-5-(2-methoxyphenyl)-3-thienyl]perfluorocyclopentene (1o). The compound displayed excellent photochromism both in solution and in PMMA film. The isomeric compound also functioned as a fluorescence switch by photoirradiation in solution. In addition, cyclic voltammetry tests showed that the electron-donating methoxyl group at the terminal benzene ring had a significant effect on the electrochemical properties of the isomeric diarylethene.

2007 ◽  
Vol 85 (1) ◽  
pp. 12-20 ◽  
Author(s):  
Tianshe Yang ◽  
Shouzhi Pu ◽  
Bing Chen ◽  
Jingkun Xu

New types of asymmetrical photochromic diarylethene derivatives having a pyrazole unit, namely 1-[1,3,5-trimethyl-1-pyrazol-4-yl],2-[2-methyl-5-(4-methoxylphenyl)-1-thien-3-yl]perfluorocyclopentene (1a), 1-[1,3,5-trimethylpyrazol-4-yl],2-[2-methyl-5-(3-methoxylphenyl)-1-thien-3-yl] perfluorocyclopentene (2a), 1-[1,3,5-trimethyl-pyrazol-4-yl],2-[2-methyl-5-(2-methoxylphenyl)-1-thien-3-yl]perfluorocyclopentene (3a), and 1-[1,3,5-trimethyl-pyrazol-4-yl],2-[2-methyl-5-phenyl-1-thien-3-yl]perfluorocyclopentene (4a), were synthesized. Their optical and electrochemical properties, such as photochromism, photochromic cyclization–cycloreversion kinetics, and fluorescence and electrochemical properties were investigated in detail. The results show that all of these compounds have good photochromism, high cycloreversion quantum yield, and relatively strong fluorescence. Their cyclization-cycloreversion processes were determined to be zeroth to first order reactions. The oxidations of diarylethenes 1a–4a were initiated at 0.73, 1.11, 0.79, and 1.03 V, respectively. Furthermore, introduction of the electron-donating methoxyl group at different positions of the terminal phenyl ring was found to strongly influence these optical and electrochemical properties.Key words: photochromism, diarylethene, electron-donating group, optical and electrochemical properties.


2014 ◽  
Vol 952 ◽  
pp. 88-91
Author(s):  
Zhao Yan Tian ◽  
Feng Xia Sun ◽  
Shou Zhi Pu

A new unsymmetrical photochromic diarylethene 1-[2-methyl-5-(1,3-difluorophenyl)-3-thienyl]-2-[2-methyl-5-(4-methoxylphenyl)-3-thienyl] perfluorocyclopentene has been synthesized,which a methoxyl group was substituted at the para-positions of the terminal phenyl ring. The photochromism of this compound was investigated, the results showed that this compound exhibited reversible photochromism, inducing cyclization and cycloreversion reactions upon alternating irradiation with UV and visible light both in solution and in a PMMA film. When irradiated 297 nm UV light, in hexane solution the maximum absorption was observed at 289 nm and 588 nm in opening-ring form and in close-ring form, respectively.


2012 ◽  
Vol 490-495 ◽  
pp. 3672-3675
Author(s):  
Hui Li ◽  
Yuan Ming Tu ◽  
Gang Liu

A new unsymmetrical photochromic diarylethene has been synthesized, namely {1-(2,5-dimethyl-3-thienyl),2-[2-methyl-5-(4-trifluoromethylphenyl)-3-thienyl]}perfluorocyclopentene. Its properties, including photochromic reactivity in solution and fluorescence property both in solution and in PMMA film were investigated. It underwent reversible cyclization and cycloreversion reactions upon alternating irradiation with UV and visible light. The isomeric compound functioned as a fluorescence switch by photoirradiation both in solution and in PMMA film. The fluorescence intensity also showed regular changes along with the change of concentration.


2011 ◽  
Vol 197-198 ◽  
pp. 522-525
Author(s):  
Wei Jun Liu ◽  
Shou Zhi Pu ◽  
Duo Hua Jiang ◽  
Pei Jian Yan

An unsymmetrical diarylethene derivative bearing both phenyl and thiophene moieties, in which a methoxyl group was substituted at the para-positions of the terminal phenyl ring, was synthesized. At the same time, its photochromic properties and fluorescence switch were investigated in detail. The results showed that this compound exhibited reversible photochromism, undergoing reversible cyclization and cycloreversion reactions upon alternating irradiation with UV and visible light both in solution and in PMMA film. The fluorescence intensity of diarylethene decreased dramatically along with the photochromism from open-ring isomer to closed-ring isomer upon irradiation with 297 nm UV light in hexane.


2012 ◽  
Vol 455-456 ◽  
pp. 17-20
Author(s):  
Hui Li ◽  
Shou Zhi Pu ◽  
Shi Qiang Cui

A new unsymmetrical isomeric diarylethene was synthesized, namely 1-(2,4-dimethyl-5-thiazolyl)-2-[2-methyl-5- (3-methoxyphenyl)-3-thienyl] perfluorocyclopentene (1o). Its photochromic reactivity both in solution and in PMMA film, photoconversion ratio at photostationary state, and fluorescence were investigated in detail. The compound displayed excellent photochromism both in solution and in PMMA film. The isomeric compound also functioned as a fluorescence switch and concentration dependence on the fluorescence spectrum in hexane.


2013 ◽  
Vol 788 ◽  
pp. 194-197
Author(s):  
Shu Hong Jing ◽  
Shou Zhi Pu ◽  
Cong Bin Fan

A new unsymmetrical isomeric diarylethene was synthesized, namely1-[2-methyl-(5-(4-hydroxyl) phenyl) -3-thieny-2-(2-methyl-3-benzothiophene) perfluorocyclopentene (1o). Its photochromic reactivity both in solution and in PMMA film, photoconversion ratio at photostationary state, and fluorescence were investigated in detail. The compound displayed excellent photochromism both in solution and in PMMA film. The isomeric compound also functioned as a fluorescence switch and concentration dependence on the fluorescence spectrum in hexane.


2011 ◽  
Vol 393-395 ◽  
pp. 389-392
Author(s):  
Hui Li ◽  
Shou Zhi Pu ◽  
Wei Jun Liu

A new photochromic diarylethene bearing an isoxazole unit has been synthesized, namely {1-(3,5-dimethyl-4-isoxazolyl), 2-[2-methyl-5-(3-methoxyphenyl)-3-thienyl]}perfluorocyclopentene. Its properties, including photochromic reactivity both in solution and in PMMA film, photoconversion ratio at photostationary state, fluorescence and optical recording property were investigated. It underwent reversible cyclization and cycloreversion reactions upon alternating irradiation with UV and visible light both in hexane and in PMMA. The isomeric compound also functioned as a fluorescence switch by photoirradiation. Using this dithienylethene as optical storage was performed successfully.


2013 ◽  
Vol 327 ◽  
pp. 89-93
Author(s):  
Shui Jun Xia ◽  
Gang Liu ◽  
Shi Qiang Cui

A novel unsymmetrical diarylethene derivative bearing thiophene moieties, in which a methyl group was substituted at the ortho-positions of the terminal phenyl ring, was synthesized. At the same time, its photochromic properties and fluorescence switch were investigated in detail. The results showed that this compound exhibited reversible photochromism, undergoing reversible cyclization and cycloreversion reactions upon alternating irradiation with UV and visible light both in solution and in PMMA film,and its absorption maxima were observed at 556 nm in hexane and at 560 nm in PMMA amorphous film, respectively, upon irradiation with 297 nm UV light. The fluorescence intensity of diarylethene decreased dramatically along with the photochromism from open-ring isomer to closed-ring isomer upon irradiation with 297 nm UV light in PMMA.


2012 ◽  
Vol 490-495 ◽  
pp. 3722-3725 ◽  
Author(s):  
Duo Hua Jiang ◽  
Gang Liu ◽  
Wei Jun Liu ◽  
Shi Qiang Cui

An unsymmetrical diarylethene derivative bearing both phenyl and benzofuranyl, in which a trifluoromethyl group was substituted at the para-positions of the terminal phenyl ring, was synthesized. At the same time, its photochromic properties and fluorescence switch were investigated in detail. The results showed that this compound exhibited reversible photochromism, undergoing reversible cyclization and cycloreversion reactions upon alternating irradiation with UV and visible light both in solution and in PMMA film, and its absorption maxima were observed at 498 nm in hexane and at 505 nm in PMMA amorphous film, respectively, upon irradiation with 297 nm UV light. In hexane solution, the open-ring isomer of the diarylethene 1 exhibited relatively strong fluorescence at 419 nm when excited at 330 nm


Materials ◽  
2020 ◽  
Vol 13 (3) ◽  
pp. 624 ◽  
Author(s):  
Alina Iuliana Pruna ◽  
Nelly Ma. Rosas-Laverde ◽  
David Busquets Mataix

Graphene oxide (GO)-modified polypyrrole (PPy) coatings were obtained by electrochemical methods in the presence of the anionic surfactant, sodium dodecyl sulfate (SDS). The structure, morphology, and electrochemical properties of the coatings were assessed by Fourier transform infrared (FTIR) spectroscopy, Raman spectroscopy, scanning electron microscopy (SEM) and cyclic voltammetry at varying scan rates, respectively. The properties of the obtained coatings were analyzed with the GO and PPy loadings and electrodeposition mode. The hybrid coatings obtained galvanostatically showed a coarser appearance than those deposited by cyclic voltammetry CV mode and improved performance, respectively, which was further enhanced by GO and PPy loading. The capacitance enhancement can be attributed to the SDS surfactant that well dispersed the GO sheets, thus allowing the use of lower GO content for improved contribution, while the choice of suitable electrodeposition parameters is highly important for improving the applicability of GO-modified PPy coatings in energy storage applications.


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