Diarylethene 1o Research Articles

Synthesis, Photochromic Properties of a Novel Unsymmetrical Hybrid Diarylethene Material with Benzene Unit

A new unsymmetrical photochromic diarylethene 1o, which is named 1-[2-methyl-5-(4-methoxyphenyl)-3-thienyl]-2-[2-methyl-5-(4-formyphenyl)-3-thienyl] perfluorocyclopentene, was synthesized. Its optical properties, including photochromic reactivity, kinetics and fluorescence properties were investigated in detail. The result indicated that the diarylethene underwent reversible photochromism, changing between colorless and blue in hexane solution and in PMMA, respectively. 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 fluorescence switching properties.

Synthesis and Properties of 1-[2-trifluoromethylpheny-2-[2-methyl-5-(3,5-difluorophenyl)-3-thienyl] perfluorocyclopentene

An asymmetrical photochromic diarylethene 1-[2-trifluoromethylpheny-2-[2-methyl-5-(3,5-difluorophenyl)-3-thienyperfluorocyclopentene (1o) was synthesized and its phtochromic, fluorescent properties in both solution and PMMA films were investigated in detail. This compound exhibited remarkable photochromism, upon irradiation with 297 nm UV light, the colorless solution of 1o turned to plum with a new visible absorption band centered at 544 nm (ε =3.75 × 103 L mol-1 cm-1) attributable to the closed-ring isomer 1c.The fluorescence intensity of diarylethene decreased dramatically along with the photochromism from open-ring isomer to closed-ring isomer in PMMA films and in hexane. The emission intensity of diarylethene 1o in a photostationary state was quenched to ca. 64% in hexane and 27% in PMMA films.

Photochromism Properties of a New Unsymmetrical Diarylethene Bearing a Benzene Unit

A new photochromic diarylethene compound 1-[(2-methyl-5-(4-trifluoromethyphenyl)-3-thienyl)]-2-{2-methyl-5-[2-(1,3-dioxolane)]-3-thienyl} perfluorocyclopentene 1O was synthesized. Its optoelectronic properties, such as photochromism in solution as well as in poly-methylmethacrylate (PMMA) amorphous films, fluorescences switch were investigated in detail. Upon irradiated UV light it changes from colorless to purple in solution and PMMA amorphous film, respectively. Finally, the diarylethene 1O was exhibited remarkable fluorescence switch properties along with the cyclization reactions. When the concentration arrived at 1 × 10-5 mol L-1, the fluorescence peak had the maximum.

Study on Photochromic Properties of 1-(2-methoxyphenyl)-2-[2-methyl-5-(1,3-dioxolane)-3-thienyl]perfluorocyclopentene

A new unsymmetrical photochromic diarylethene 1o, which is named 1-(2- methoxyphenyl)-2-[2-methyl-5-(1,3-dioxolane)-3-thienyl]perfluorocyclopentene, was synthesized. Its photochromic and simulated molecule structure were also investigated in detail. This diarylethene underwent reversible photochromism, changing between colorless and blue in hexane solution upon appropriate irradiation with UV/vis light. The kinetic experiments illustrated that the cyclization/cycloreversion process of this compound was determined to be the zeroth/first reaction. In addition, this compound can be used as optical recording materials.

Synthesis and Application of Photochromic Materials in Holographic Recording of a Asymmetrical Diarylethene

A novel unsymmetrical diarylethene derivative containing thiophene moieties, in which a methoxy group was substituted at the para-positions of the terminal phenyl ring, was synthesized. Its photochromic properties were investigated in detail, the results indicated that the diarylethene 1o changed the color from colorless to blue, which the absorption maxima were observed at 611 and 627 nm in hexane and PMMA film when irradiation with 297 nm UV light. Additionally, the open-ring isomer of the diarylethene 1o exhibited relatively strong fluorescence at 305 nm in hexane when excited at 322 nm and the fluorescence intensity progressively decreased accompany with the photocyclization occurs. Finally, using this diarylethene as recording medium, polarization optical recording was carried out successfully.

Synthesis, Photochromic Properties of a Hybrid Diarylethene Material with a Benzene Unit

A new photochromic diarylethene compound [1-(2-methyl-5-phenyl-3-thienyl)-2-(2-methyl-5-1,3-dioxolane-3-thienyl)] perfluorocyclopentene 1o was synthesized and its photochromic properties and fluorescence switch were investigated in detail. Upon irradiated UV light it changes from colorless to purple in solution and PMMA amorphous film, respectively. Finally, the diarylethene 1o was exhibited remarkable fluorescence switch properties along with the cyclization reactions. When the concentration arrived at 5 × 10-5 mol L-1, the fluorescence peak had the maximum.

Photochemistry Properties of a Novel Photochromic Diarylethene Derivative

A new unsymmetrical photochromic diarylethene, 1-[2, 4-dimethyl-5-thiazoly-2-[2-methyl-5-(3-methylphenyl)-3-thienyperfluorocyclopentene (1o) were synthesized, and its properties, such as photochromism in solution as well as in poly-methylmethacrylate (PMMA) amorphous films, and fluorescence properties were investigated in detail. The results showed the compound exhibited good photochromism in hexane solution and in PMMA amorphous film, the maxima absorption of its closed-ring isomer 1c are 492 nm and 498 nm respectively. The open-ring isomer of the diarylethene 1 exhibited relatively strong fluorescence at 465 nm in hexane solution (5 × 10-5 mol/L) when excited at 289 nm. 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.

Synthesis and Properties of a Novel Photochromic Diarylethene 1-(2,4-dimethyl-5-thiazolyl)-2-[2-methyl-5-(4-formylphenyl)-3-thienyl]perfluorocyclopentene

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.

Study on Photochromic Compounds with Synthesis Photochromic Diarylethenes Based on Five-Membered Heterocycle and Benzenze Ring

A novel photochromic diarylethene 1-{[2-methyl-5-formyl-3-thieny}-2-[2-methyl-5-(2-cyanophenyl)-3-thienyperfluorocyclopentene (1o) has been synthesized for the examination of its properties including photochromism, fluorescence properties and optical recording. The concentration effect in hexane solution was investigated also. The result indicated that the diarylethene 1o changed the color from colorless to royalblue upon irradiation with 297 nm UV light, in which absorption maxima were observed at 592 and 603 nm in hexane and PMMA film, respectively. The colorless open form with fluorescence character could be regenerated by irradiation with visible light. In hexane solution, when the concentration at 2 × 10-5 mol/L the fluorescence peak have the maximum. The cyano group and its substituted position can availably modulate the optical and electrochemical behaviours of these diarylethene derivatives. In addition, polarization optical recording using this diarylethene as recording medium was performed successfully.

Study on Material Properties with Synthesis and Properties of a Photochromic Diarylethene with Acetal Unit

A new unsymmetrical photochromic diarylethene with an acetal unit was synthesized and its photochromic and fluorescent properties were also investigated. The compound exhibited remarkable photochromism both in solution and PMMA film. In PMMA film, the open-ring isomer of the diarylethene 1o exhibited relatively strong fluorescence at 377 nm when excited at 372 nm. All results indicated that the acetal unit played an important role during the process of photochromic reaction for the diarylethene derivatives.

Synthesis and Application of a New Diarylethene with Composite Properties for Polarization Holographic Recording

A new unsymmetrical photochromic diarylethene bearing a benfuran and a thiophene aryl unit 1-(2-methyl-3-benfuran)-2-{2-methyl-5-[2-(1,3-dioxolane)]-3-thienyl}perfluorocyclopentene (1o) has been synthesized. It’s optoelectronic properties, such as photochromism in solution as well as in polymethylmethacrylate(PMMA) amorphous films, fluorescence and photon-mode polarization multiplexing holographic recording were investigated. Diarylethene 1o changed the color from colorless to red upon irradiation with 313 nm UV light, in which absorption maxima were observed at 509 nm in hexane and at 520 nm in PMMA amorphous film, respectively. This new photochromic system also exhibited remarkable fluorescence intensity and clear fluorescent switches by photo irradiation in solution. Finally, rewritable holographic optical storage using 1a was performed.

Study on Advanced Composite Synthesis of a New Photochromic Diarylethene Materials with Bearing Thiophene Units

A novel unsymmetrical photochromic diarylethene bearing bisthiophene moiety 1-[2,5-dimethyl-3-thienyl]-2-[2-methyl-5-(2-methylphenyl)-3-thienyl]perfluoroyclopentene (1o) was synthesized and its photochromic, fluorescent and optical storage properties were also investigated. The compounds exhibited remarkable photochromism both in solution and in PMMA film. The result indicated that the diarylethene 1o changed the color from colorless to purple upon irradiation with 297 nm UV light, in which absorption maxima were observed at 527 and 541 nm in hexane and PMMA film, respectively. The open-ring isomer of the diarylethene 1 also exhibited relatively strong fluorescence both in hexane and PMMA film. The fluorescence intensity declined along with the photochromism upon irradiation with 297 nm light. In addition, optical recording using diarylethene 1c as recording medium was carried out successfully.

Properties and Application of a Novel Diarylethene Photochromism Material with a Naphthyl Ring

A new unsymmetrical photochromic diarylethene 1-(2-methylnaphthyl)-2-(2-n-butyl-5-formyl-3-thienyl) perfluorocyclopentene (1o), was synthesized and its optoelectronic properties, such as photochromism in solution as well as in poly-methylmethacrylate (PMMA) amorphous films, and the fluorescence spectra of diarylethene 1o were investigated. The diarylethene can be potentially used as holographic optical recording medium

Photochromism and Fluorescence of a Novel Unsymmetrical Diarylethene Material Bearing Benzene and Thiophene Ring

A new photochromic diarylethene compound, 1-[2-methyl-(5-(4- dioxolane) phenyl)-3-thienyl]-2-(2-methyl-3-benzothiophene)perfluorocyclopentene (1o)was synthesized. Its properties, including photochromism and fluorescence were investigated in detail both in solution and PMMA amorphous film. It underwent reversible cyclization and cycloreversion reactions upon alternating irradiation with UV and visible light in hexane. The compound showed good phtochromism both in solution and in solid states. Diarylethene 1o changed the color from colorless to purple upon irradiation with 297 nm UV light, in which absorption maxima were observed at 539 nm in hexane and at 547nm in PMMA film, respectively. Using diarylethene 1c/PMMA film as recording medium, optical recording was performed successfully. This new photochromic system also exhibited remarkable optical storage character

Synthesis of a Photochromic Diarylethene Material Bearing Fluorine Atoms for Rewritable Holographic Optical Storage

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

Synthesis a New Function Materials and Photochromic Properties of Diarylethene Bearing a Naphthalene and Isoxazole Moiety

A new photochromic diarylethene compound 1-(2-methylnaphthyl)-2-(3, 5-dimethyl-4-isoxazolyl)perfluorocyclopentene (1o), was synthesized and its photochromic and fluorescent properties were investigated. Diarylethene 1o changed the color from colorless to yellow upon irraditation with 297 nm UV light, which the absorption maxima were observed at 446 nm in hexane solution. The kinetic experiments indicated that the cyclization/cycloreversion process of the compound was determined to be the zeroth/first order reaction in hexane solution. The fluorescence intensity decreased along with the photochromism upon irradiation with 297 nm light and its closed-ring isomer showed weak fluorescence

Synthesis and Properties of a Novel Photochromic Diarylethene Material Bearing Two Five-Membered Aryl Unit

A new unsymmetrical photochromic diarylethene, 1-(2,5-dimethyl-3-thienyl)-2-(2 -methyl-5-p-tolyl-3-thienyl)perfluorocyclopentene (1) was synthesized, and its photochromic and fluorescence properties were investigated. The results showed the compound exhibited good photochromism in hexane solution and in PMMA amorphous film with alternating irradiation by UV/Vis light, the maxima absorption of its closed-ring isomer 1c are 541 nm and 551 nm respectively. The open-ring isomer of the diarylethene 1 exhibited relatively strong fluorescence at 360 nm in hexane solution (5 × 10-5 mol/L) when excited at 305 nm. 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 1 in hexane increase from 1 × 10-6 mol/L to 1 × 10-3 mol/L, the fluorescence intensity of the open-ring isomer become strong first, then become weak

Efficient Synthesis and Photochromic Properties of a New Unsymmetrical Photochromic Diarylethene Base on Naphthalene Unit

A new diarylethenes [1-(2-methyl-1-naphthyl), 2-(2-methyl-5-1,3-dithiolane-3-thienyl)]perfluorocyclopentene 1o based on a hybrid structure of naphthalene and thiophene has been developed. Its properties including photochromism, kinetics and fluorescence were investigated in detail. The results indicated that the compound exhibited good photochromism, which changing from colorless to orange after irradiation with 297 nm UV light both in solution and in PMMA film. The fluorescence switching properties shown the fluorescence spectrum of diarylethene 1o was decreased remarkable along with the cyclization reactions. Finally, using this diarylethene as recording medium, polarization optical recording was carried out successfully.

Photochromic, Kinetics, and Fluorescence of a Novel Diarylethene

A new unsymmetrical photochromic diarylethene, 1-(2-ethyl-3-benzofuranyl)-2-(2,5 -dimethyl-3-thienyl)perfluorocyclopentene (1) was synthesized, and its photochromic properties and kinetics of the photochromic cyclization/cycloreversion were investigated. The results showed that the cyclization/cycloreversion process of these compounds were determined to be the zeroth/first order reaction.The compound exhibited good photochromism in hexane solution with alternating irradiation by UV/Vis light, and the maxima absorption of its closed-ring isomer 1c are 502 nm. The open-ring isomer of the diarylethene 1 exhibited relatively strong fluorescence at 402 nm in hexane solution (2 × 10-5 mol/L) and 412 nm in PMMA amorphous film when excited at 312 nm and 310 nm,respectively. The fluorescence intensity decreased along with the photochromism upon irradiation with 297 nm light and its closed-ring isomer showed almost no fluorescence.The fluorescence spectra of diarylethene 1o depended on the concentration.

Synthesis and Properties of a New Type Diarylethene Bearing Benzo[b]thiophen Aryl Unit

A new type photochromic diarylethene, 1-(2-methyl-3-benzothiophenyl)-2- [2-methyl-5-(3,5-difluorophenyl)-3-thienyl]perfluorocyclopentene (1o) was synthesized, and its photochromic and fluorescent properties were investigated. This compound exhibited reversible photochromism, changing from colorless to pink after irradiation with UV light both in solution and in PMMA amorphous film. In addition, the fluorescence spectra of diarylethene 1o evidently depended on the concentration in hexane.