Photochromism and Optical Recording of a Novel Diarylethene Bearing Phenanthrene Unit

2013 ◽  
Vol 763 ◽  
pp. 79-83 ◽  
Author(s):  
Xue Li ◽  
Cong Bin Fan ◽  
Gang Liu

Photochromic molecules are part of a large class of materials in which light stimulus not only induces a color variation but also affects other physicochemical properties. In the paper, an asymmetrical photochromic diarylethene, 1-(2,4-dimethyl-3-thiazole)-2-[2-methyl-5-(10-phenanthrenyl)-3-thienyPerfluorocyclopentene was synthesized and its photochromic and fluorescent properties were systematically investigated. The compound exhibited remarkable photochromic, changing from colorless to OrangeRed after irradiation with UV light both in solution and in PMMA film. In addition, its fluorescence property was also discussed. When irradiation with UV light, the fluorescence intensity declined remarkably. The results showed that the diarylethene exhibited a relatively strong fluorescence switch along with the photochromism from open-ring isomer to closed-ring isomer. Using this diarylethene 1a as optical storage was performed successfully.

2011 ◽  
Vol 239-242 ◽  
pp. 3290-3293
Author(s):  
Hong Liang Liu ◽  
Shou Zhi Pu ◽  
Wei Jun Liu ◽  
Shi Qiang Cui

A novel photochromic diarylethene based on isoxazole moiety was synthesized and its photochromic and fluorescent properties were also investigated. It underwent reversible cyclization and cycloreversion reactions upon alternating irradiation with UV and visible light in hexane and in PMMA film. The compound exhibited remarkable photochromism, changing from colorless to purple after irradiation with UV light. When irradiation with UV light, the fluorescence intensity declined remarkably. The results showed that the diarylethene exhibited a relatively strong fluorescence switch along with the photochromism from open-ring isomer to closed-ring isomer. Using this dithienylethene 1c as optical storage was performed successfully.


2011 ◽  
Vol 295-297 ◽  
pp. 1070-1073
Author(s):  
Hong Liang Liu ◽  
Gang Liu ◽  
Shi Qiang Cui ◽  
Wei Jun Liu

A novel photochromic diarylethene based on isoxazole moiety was synthesized and its photochromic and fluorescent properties were also investigated. This compound exhibited reversible photochromism, changing from colorless to red after irradiation with UV light both in solution and in poly-methyl methacrylate (PMMA) amorphous film. Also, it exhibited remarkable fluorescence switching in the solid state. The results showed that the diarylethene exhibited a relatively strong fluorescence switch along with the photochromism from open-ring isomer to closed-ring isomer. Using this dithienylethene 1c as optical storage was performed successfully.


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.


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.


2011 ◽  
Vol 197-198 ◽  
pp. 421-424
Author(s):  
Duo Hua Jiang ◽  
Shou Zhi Pu ◽  
Wei Jun Liu ◽  
Pei Jian Yan ◽  
Ming Liu

A novel unsymmetrical diarylethene derivative bearing both phenyl and thiophene moieties, in which a trifluoromethyl 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 584 nm in hexane and at 593 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 420 nm when excited at 322 nm.


2013 ◽  
Vol 830 ◽  
pp. 290-293
Author(s):  
Shui Jun Xia ◽  
Hai Chang Ding ◽  
Gang Liu

A novel photochromic diarylethene based on thiophene and a six-membered aryl moieties 1-(2-methyl-5-chloro-3-thienyl)-2-(2-trifluoromethylphenyl) perfluorocyclopentene has been 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 in PMMA film. The fluorescence intensity of diarylethene decreased along with the photochromism from open-ring isomer to closed-ring isomer upon irradiation with 254 nm UV light in PMMA. The fluorescence intensity decreases along with the increase of solution concentration.


2011 ◽  
Vol 327 ◽  
pp. 53-56
Author(s):  
Hong Liang Liu ◽  
Shou Zhi Pu ◽  
Shi Qiang Cui ◽  
Wei Jun Liu

A novel photochromic diarylethene based on pyrazole moiety was synthesized and its photochromic and fluorescent properties were also investigated. The compound exhibited remarkable photochromism, changing from colorless to purple after irradiation with UV light both in solution and in PMMA film. In hexane solution and in PMMA film, the open-ring isomer of the diarylethene 1 exhibited relatively remarkable fluorescence. The results indicated that the pyrazole moiety played a very important role during the process of photochromic reaction for the diarylethene derivative. Using this dithienylethene 1c 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 164 ◽  
pp. 166-169 ◽  
Author(s):  
Shang Hua He ◽  
Wei Jun Liu ◽  
Gang Liu

Photochromism is referred to as a photoinduced reversible transformation reaction between two isomers, open and closed, with different absorption spectra upon irradiation with light of an appropriate wavelength. A new photochromic diarylethene, 1-[2-methyl-5-(3, 5-difluorophenyl)-3-thienyl]-2-(2-methyl-3-benzofuran)perfluorocyclopentene(1o), has ben synthesized. The compound showed good phtochromism both in solution and in solid states. Diarylethene 1o changed the color from colorless to magenta upon irradiation with 313 nm UV light, in which absorption maxima were observed at 523 nm in hexane and at 529 nm in PMMA film, respectively. Especially, the diarylethene exhibited a relatively strong fluorescence switches along with the phtochromism from open-ring isomers to closed-ring isomers in solid states. Using diarylethene 1c/PMMA film as recording medium, optical recording was performed successfully. This new photochromic system also exhibited remarkable optical storage character


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