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

2014 ◽  
Vol 662 ◽  
pp. 103-106
Author(s):  
Le Le Ma ◽  
Gang Liu

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.

2014 ◽  
Vol 886 ◽  
pp. 168-171 ◽  
Author(s):  
Le Le Ma ◽  
Hong Yan Xu ◽  
Shou Zhi Pu

A new unsymmetrical photochromic diarylethene 1-(2-methyl-3-benzothiophene)-2-(2-methyl-5-aminomethane-3-thienyl) perfluorocyclopentene was synthesized and its optoelectronic properties, such as photochromism and the fluorescence spectra of diarylethene1oin acetonitrile solution was investigated. The compound exhibited good photochromism in solution with alternating irradiation by UV/Vis light, and the maxima absorption of its closed-ring isomer1care 530 nm. The open-ring isomer of the diarylethene1oexhibited relatively strong fluorescence at 375 nm. Its fluorescence intensity decreased along with the photochromism from open-ring isomers to closed-ring isomers upon irradiation with 297 nm UV light.


2014 ◽  
Vol 1003 ◽  
pp. 35-38
Author(s):  
Le Le Ma ◽  
Hong Yan Xu ◽  
Gang Liu

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.


2013 ◽  
Vol 473 ◽  
pp. 81-84
Author(s):  
Yong Jun Tang ◽  
Hong Yan Xu ◽  
Shou Zhi Pu

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.


2013 ◽  
Vol 763 ◽  
pp. 57-60
Author(s):  
Wei Wei Geng ◽  
Shi Qiang Cui ◽  
Shou Zhi Pu

A unsymmetrical photochromic diarylethene, 1-(2,5-dimethyl thiazole)-2-[4-(2-cyanophenyl)-3-thieny} perfluorocyclopentene (1a),was synthesized, and its optoelectronic properties were also investigated in detail. The results showed that this compound exhibited reversible photochromism, changing from colorless to orange red after irradiation with UV light both in solution and in PMMA amorphous film.The open-ring isomer of the diarylethene 1 exhibited relatively strong fluorescence at 432 nm when excited at 384 nm. The fluorescence intensity declined along with the photochromism upon irradiation with 297 nm light.The diarylethene exhibited a fluorescence switches along with the photochromism from open-ring isomers to closed-ring isomers. When irradiated by UV light, the photocyclization reaction was occurred and the emission intensity of the diarylethene decreased significantly, due to producing the non-fluorescence closed-ring isomers. The back irradiation by appropriate wavelength visible light regenerated its open-ring isomers and recovered the original emission intensity.


2014 ◽  
Vol 1078 ◽  
pp. 102-105
Author(s):  
Gang Li ◽  
Gang Liu ◽  
Shou Zhi Pu

A novel unsymmetrical photochromic diarylethene compound 1-(2-methyl-3-benzothienyl)-2-[3-methyl-2-thienyl] perfluorocyclopentene was designed and constructed successfully. Its optoelectronic properties have been discussed systematically, such as photochromic, fluorescence switch, kinetics experiments in hexane solution and PMMA. The consequences showed that this compound exhibited good reversible photochromism. The maxima absorption of compound closed-ring isomer 1c is 468nm. Upon irradiation with 297nm UV light, Its fluorescence intensity decreased along with the photochromism from open-ring isomers to closed-ring isomers upon irradiation with 297 nm UV light.


2014 ◽  
Vol 1078 ◽  
pp. 110-113
Author(s):  
Le Le Ma ◽  
Hong Yan Xu ◽  
Qing Zhang ◽  
Gang Liu

A new fluorescent switch based on a photochromic diarylethene, 1-[2-methyl-5-(4-hydroxymethylphenyl)-3-thienyl]-2-[2-methyl-5-(4-azidomethylphenyl)-3-thienyl] perfluorocyclopentene has been synthesized, And its properties have been discussed systematically in acetonitrile solution and in PMMA, such as photochromic, fluorescence switch and kinetics experiments, and its optoelectronic properties, The results showed that this compound exhibited reversible photochromism and the maxima absorption of compound closed-ring isomer 1c is 590 nm. Its fluorescence intensity decreased along with the photochromism from open-ring isomers to closed-ring isomers.


2011 ◽  
Vol 474-476 ◽  
pp. 1591-1594
Author(s):  
Gang Liu ◽  
Ming Liu ◽  
Qing Zhang ◽  
Shou Zhi Pu ◽  
Wei Jun Liu

A unsymmetrical photochromic diarylethene, 1-[2-methyl-5-(3,4-difluorophenyl) -3-thienyl]-2- (2-cyano-1,5-dimethyl-4-pyrryl) perfluorocyclopentene (1o), 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 both in solution and in PMMA amorphous film. The open-ring isomer of the diarylethene 1 exhibited relatively strong fluorescence both in hexane solution. The fluorescence intensity decreased along with the photochromism upon irradiation with 297 nm light and its closed-ring isomer showed almost no fluorescence. Using diarylethene 1 as recording medium, polarization holographic optical recording was carried out successfully.


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 239-242 ◽  
pp. 2415-2418
Author(s):  
Gang Liu ◽  
Ming Liu ◽  
Shou Zhi Pu

An unsymmetrical photochromic diarylethene, 1-[2-methyl-5-(3,5-difluorophenyl)-3-thienyl]-2-(2-cyano-1,5-dimethyl-4-pyrryl)perfluorocyclopentene (1o), 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 both in solution and in PMMA amorphous film. The open-ring isomer of the diarylethene 1 exhibited relatively strong fluorescence both in hexane solution and in PMMA amorphous film. The fluorescence intensity decreased along with the photochromism upon irradiation with 297 nm light and its closed-ring isomer showed almost no fluorescence.


2014 ◽  
Vol 707 ◽  
pp. 40-43
Author(s):  
Yong Juan Tang ◽  
Shui Jun Xia ◽  
Shi Qiang Cui ◽  
Shou Zhi Pu

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.


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