Efficient Synthesis and Photochromic Properties of a New Diarylethene Bearing a Condensed Aromatics Moiety

2012 ◽  
Vol 455-456 ◽  
pp. 33-36
Author(s):  
Ren Jie Wang ◽  
Hong Ying Xia ◽  
Gang Liu ◽  
Shi Qiang Cui

A new class of diarylethenes based on a hybrid structure of thiophene and naphthalene has been developed and its properties including photochromism, kinetics and fluorescence were investigated in detail. The results showed that the compound exhibited obvious photochromism, changing from colorless to red after irradiation with 297 nm UV light both in solution and in PMMA film. The kinetic experiments indicated that the cyclization/cycloreversion process of the compound was determined to be the zeroth/first order reaction in hexane solution. At last, the results demonstrated that the diarylethene compound had attractive properties for potential application in optical storage.

2010 ◽  
Vol 156-157 ◽  
pp. 462-466
Author(s):  
Shi Qiang Cui ◽  
Shou Zhi Pu ◽  
Gang Liu ◽  
Wei Jun Liu

A new photochromic compound 1-[2,5-dimethyl-3-thienyl]-2-[2-methyl-5-pyridine-3-yl-3-thieyl] perfluoroyclopentene(1a) was synthesized, its photochromic properties were examined, the result indicated that the color of the compound 1a changed from colorless to a purple one upon irradiation with 297 nm UV light, a new absorption maxima were observed at 549 and 553 nm in hexane and PMMA film, respectively. The the photochromic reaction kinetics indicated that the cyclization processes of 1 belong to the zeroth order reaction and the cycloreversion process belong to the first order reaction.This new photochromic system also exhibited remarkable optical storage character.


2011 ◽  
Vol 295-297 ◽  
pp. 1038-1041
Author(s):  
Ren Jie Wang ◽  
Gang Liu ◽  
Hong Ying Xia ◽  
Shi Qiang Cui

A novel photochromic diarylethene bearing a six-membered aryl unit, 1-[2-methyl-5-(3-fluorophenyl)-3-thienyl]-2-(2-methoxylphenyl)perfluorocyclopentene (1o), was synthesized and its photochromic properties, fluorescence switch and optical recording were investigated in detail. This compound exhibited remarkable photochromism, changing from colorless to blue after irradiation with 297 nm UV light both in solution and in PMMA film, respectively. The new diarylethene also exhibited excellent fluorescence intensity and fluorescence switches by photoirradiation in hexane solution. Finally, photo-mode rewritable optical storage using 1o was performed. The images demonstrated that the compound as optical storage material was very sensitive responding to 633 nm recording laser, and the recorded-signals were provided with high S/N ratio.


2012 ◽  
Vol 490-495 ◽  
pp. 3733-3737
Author(s):  
Shu Hong Jing ◽  
Shou Zhi Pu ◽  
Shi Qiang Cui

A new photochromic diarylethene compound, 1-(2,4-dimethoxy-5-pyrimidine)-2-[2-methyl-5-(3-pyridine)-3-thienyl]perfluorocyclopentene(1a), was synthesized, and its photochromic reactivity, fluorescent and electrochemical property were also investigated. Diarylethene 1a changed the color from colorless to pink upon irradiation with UV light, in which absorption maxima were observed at 520 and 519 nm in hexane and PMMA film, respectively. The the photochromic reaction kinetics indicated that the cyclization processes of 1 belong to the zeroth order reaction and the cycloreversion process belong to the first order reaction. This new photochromic system also exhibited remarkable fluorescence switching in hexane solution and this new photochromic system also exhibited remarkable optical storage character.


2013 ◽  
Vol 327 ◽  
pp. 78-82
Author(s):  
Zhi Yuan Sun ◽  
Xiao Dan Zhang ◽  
Shi Qiang Cui ◽  
Shou Zhi Pu

A novel unsymmetrical photochromic diarylethene 1-(2-methyl-3-benzofuran)-2-[5-(2-methylbenzene)-2-methyl-3-thieny perfluorocyclopentene1owas synthesized, then its photochromic, Kinetics and fluorescence properties were investigated. The results showed that the diarylethene compound had good photochromism upon irradiation with 297 nm UV light, in which the absorption maximum were observed at 510 nm in hexane solution and 524 nm in poly methyl methacrylate (PMMA) film. Besides, the cyclization and cycloreversion process of the compound were determined to be the zeroth and first order reaction by UV-Vis spectra, respectively. And, the open-ring isomer of the diarylethene exhibited relatively stronger fluorescence at 427 nm when excited at 273 nm in hexane solution.


2012 ◽  
Vol 583 ◽  
pp. 105-108
Author(s):  
Shi Qiang Cui ◽  
Yan Hua Yang ◽  
Shou Zhi Pu

Photochromism; Diarylethene materials; Fluorecence; Reaction kinetics. Abstract. A new unsymmetrical photochromic diarylethene, 1-(2-methyl-5-phenyl-3-thienyl)-2-[2-methyl-5-(4-formyl-phenyl)-3-thienyl]perfluorocyclopentene (1a), was synthesized, and its photochromic properties and reaction kinetics were investigated, respectively. The compound exhibited good photochromism both in solution and in PMMA film with alternating irradiation by UV/Vis light. The cyclization processes of compound 1a belong to the zeroth order reaction, while the cycloreversion processes belong to the first order reaction. The optical recording results indicated that the new photochromic diarylethene can be applied in high capacity optical storage.


2014 ◽  
Vol 1003 ◽  
pp. 27-30
Author(s):  
Guan Ming Liao ◽  
Dan Dan Xue ◽  
Chun Hong Zheng ◽  
Shou Zhi Pu

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.


2014 ◽  
Vol 1003 ◽  
pp. 55-58
Author(s):  
Dan Dan Xue ◽  
Guan Ming Liao ◽  
Chun Hong Zheng ◽  
Shou Zhi Pu

A new photochromic diarylethene compound bearing a rhodamine B unit, 1-(2-methyl-3-benzofuryl)-2-{2-methyl-5-[4-formyloxyethyl (rhodamine-B)] phenyl-3-thienyl} perfluorocyclopentene (1o) was synthesized, and its photochromic properties such as photochromism in solution as well as in a polymethylmethacrylate (PMMA) amorphous film were investigated specfically. 1o exhibits good photochromism upon alternating irradiation with UV light and visible light (> 510 nm) in hexane and a PMMA film. The kinetic experiments showed that the cyclization and cycloreversion processes were zeroth and first order reaction, respectively.


2010 ◽  
Vol 156-157 ◽  
pp. 665-669
Author(s):  
Tao Feng Wang ◽  
Zhi Gang Liu ◽  
Shou Zhi Pu ◽  
Gang Liu

A new unsymmetrical photochromic diarylethene 1-[2,5-dimethyl-3-thienyl]-2-[3,5-difluorophenyl]perfluoroyclopentene (1a) was synthesized, its photochromic, fluorescent and optical strorage properties were examined, the result indicated that the diarylethene 1a changed the color from colorless to purple upon irradiation with 313 nm UV light, in which absorption maxima were observed at 542nm and 556nm in hexane and PMMA film, respectively. This new photochromic system exhibited remarkable fluorescence intensity and clear fluorescent switches by photoirradiation in PMMA film. The results showed that the cyclization/cycloreversion process of the compound was determined to be the zeroth/first order reaction. This new photochromic system also exhibited remarkable optical storage character.


2012 ◽  
Vol 164 ◽  
pp. 280-283
Author(s):  
Wei Jun Liu ◽  
Wei Ping Wang ◽  
Duo Hua Jiang ◽  
Gang Liu

An unsymmetrical diarylethene derivative was synthesized, and 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 574 nm in hexane and at 579 nm in PMMA amorphous film, respectively, upon irradiation with 297 nm UV light. The diarylethene 1a in hexane solution exhibited relatively strong fluorescence at 413 nm when excited at 322 nm. The fluorscence intensity is highest at the concentration of 1.0×10-4 mol/L when excited at 322 nm.


2011 ◽  
Vol 295-297 ◽  
pp. 220-223
Author(s):  
Tao Feng Wang ◽  
Gang Liu ◽  
Shi Qiang Cui

A new unsymmetrical photochromic diarylethene of bis (1,3,5-trimethyl-4-pyrazole)ethane and bis(2-methyl-3-benzofuran)ethane was synthesized, its photochromic, fluorescent and optical strorage properties were examined, the result indicated that the diarylethene 1a changed the color from colorless to violet upon irradiation with 297 nm UV light, in which new absorption maxima were observed at 539nm and 556nm in hexane and PMMA film, respectively. This new photochromic system exhibited remarkable fluorescence intensity and clear fluorescent switches by photoirradiation in hexane. The results showed that the cyclization/cycloreversion process of the compound was determined to be the zeroth/first order reaction. This new photochromic system also exhibited remarkable optical storage character.


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