Efficient Synthesis, Photochromism and Application of a Photochromic Diarylethene Bearing a Benzene Unit

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 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.


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.


2013 ◽  
Vol 788 ◽  
pp. 211-214
Author(s):  
Jun Jie Song ◽  
Gang Liu ◽  
Ren Jie Wang

A novel unsymmetrical isomeric photochromic diarylethene based on benzofuran, 1-[2-methyl-3-benzofura-2-[2-methyl-5-(10-phenanthrenyl)-3-thienyperfluorocyclopentene, was designed and synthesized. Its fluorescent and photochromic properties were also investigated in detail. The compound exhibited excellent photochromism, changing from colorless to hot pink after irradiation with UV light both in solution and in PMMA film. Furthermore, the fluorescence intensity of the photochromic diarylethene 1a declined remarkably, when irradiation with UV light. Using this diarylethene 1a as optical storage and fluorescence switches was performed successfully.


2011 ◽  
Vol 239-242 ◽  
pp. 1609-1612
Author(s):  
Shi Qiang Cui ◽  
Shou Zhi Pu ◽  
Wei Jun Liu

A new photochromic compound 1-(2-ethyl-3-benzothienyl)-2- (2-n-propyl-5-formyl-3-thienyl) perfluorocyclopentene (1a) was synthesized, its photochromic properties were examined, the result indicated that the color of the compound 1a changed from colorless to a blue one upon irradiation with 297 nm UV light, a new absorption maxima were observed at 578 and 587 nm in hexane and PMMA film, respectively. The diarylethene 1a exhibited relatively strong fluorescence in hexane solution and the fluorescence intensity decreased along with the photochromism upon irradiation with 297 nm light. This new photochromic compound also exhibited remarkable holographic optical recording 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.


2013 ◽  
Vol 788 ◽  
pp. 198-202
Author(s):  
Xiao Ting Li ◽  
Hui Li ◽  
Shi Qiang Cui

A new unsymmetrical photochromic diarylethene, 1-(2, 4-dimethyl-5-thiazolyl)-2-[2-methyl-5-(4-formylphenyl)-3-thienyperfluorocyclopentene (1o) were synthesized. At the same time, its photochromic properties and fluorescence switch were investigated in detail. The results showed 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 of closed-ring isomer 1c were observed at 501 nm in hexane and at 510 nm in PMMA amorphous film, respectively, upon irradiation with 297 nm UV light. The open-ring isomer of the diarylethene 1 exhibited relatively strong fluorescence at 449 nm in hexane solution (2 × 10-5 mol/L) and 450 nm in PMMA amorphous film when excited at 300 nm and 292 nm, respectively. The fluorescence intensity decreased along with the photochromism upon irradiation with 297 nm light. The fluorescence intensity of diarylethene 1o also depended on the concentration. When the concentration of diarylethene 1o in hexane increase from 1 × 10-6 mol/L to 2 × 10-4 mol/L, the fluorescence intensity of the open-ring isomer become strong first, then become weak.


2014 ◽  
Vol 1003 ◽  
pp. 39-42
Author(s):  
Jun Jie Song ◽  
Gang Liu

A novel isomeric photochromic diarylethene, 1-(2-methyl-5-phenyl-3-thienyl)-2-[2-methyl-5-(4-pentylphenyl)-3-thienyl] perfluorocyclopentene, was designed and synthesized. Its fluorescent and photochromic properties were also studied in detail. The compound exhibited excellent photochromism, changing from colorless to bule after irradiation with UV light both in solution and in PMMA film. In addition, the fluorescence intensity of the photochromic diarylethene 1a declined remarkably, when irradiation with UV light.


2011 ◽  
Vol 295-297 ◽  
pp. 216-219
Author(s):  
Duo Hua Jiang ◽  
Gang Liu ◽  
Wei Jun Liu ◽  
Shi Qiang Cui

A novel unsymmetrical diarylethene derivative bearing both indole and thiophene moieties, in which a cyanol group was substituted at the meta-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 592 nm in hexane and at 607 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. In hexane solution, the open-ring isomer of the diarylethene 1 exhibited relatively strong fluorescence at 426 nm when excited at 350 nm.


2012 ◽  
Vol 602-604 ◽  
pp. 892-895
Author(s):  
Gang Liu ◽  
Long Liang ◽  
Duo Hua Jiang

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 599 nm in hexane and at 609 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 light in PMMA. In hexane solution, the open-ring isomer of the diarylethene 1 exhibited relatively strong fluorescence at 419 nm when excited at 309 nm. The fluorescence intensity is highest at the concentration of 5.0×10-5 mol/L when excited at 309 nm.


2012 ◽  
Vol 455-456 ◽  
pp. 13-16
Author(s):  
Duo Hua Jiang ◽  
Gang Liu ◽  
Wei Jun 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 548 nm in hexane and at 558 nm in PMMA amorphous film, respectively, upon irradiation with 297 nm UV light. The PMMA film of the diarylethene 1a exhibited relatively strong fluorescence at 413 nm when excited at 311 nm. The fluorscence intensity is highest at the concentration of 1.0×10-4 mol/L when excited at 311 nm.


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