Dithienylethenes with a Novel Photochromic Performance

Morimitsu, Kentaro; Shibata, Katsunori M.; Kobatake, Seiya; Irie, Masahiro

doi:10.1021/jo020114o

Cited by 152 publications

(92 citation statements)

References 22 publications

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“…Diarylethenes bearing a pyrazole unit have a relatively high cycloreversion quantum yield [27], whereas dithienylethenes bearing bulky alkoxy groups at 2-and 2 0 -positions of the thiophene rings have a very small cycloreversion quantum yield [28]. Kawai et al reported the triangular terthiophene derivatives which showed reversible photochromic reactions with high cyclization quantum yields [29].…”

Section: Introductionmentioning

confidence: 99%

Effects of substitution on the optoelectronic properties of photochromic diarylethenes bearing a pyrrole moiety

Liu

Wang

et al. 2011

Dyes and Pigments

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Section: Introductionmentioning

confidence: 99%

Effects of substitution on the optoelectronic properties of photochromic diarylethenes bearing a pyrrole moiety

Liu

Wang

et al. 2011

Dyes and Pigments

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“…This unstable blue-colored closed ring returns to the colorless open-ring form with a half life time of 37 s, which requires a thermal fading activation energy of 32.5 kJ mol −1 [68]. Furthermore, the introduction of bulky substituents at the reacting positions of dithenylethenes decreases the thermal stability of the closed-ring isomers at higher temperatures [69]. An extraordinarily high thermal stability of t 1/2 = 4.7 × 10 5 years was shown for a closed-ring isomer of 1,2-bis(5-methyl-2-phenylthiazol-4-yl) perfluorocyclopentene at 30 • C [70].…”

Section: Diarylethenesmentioning

confidence: 99%

Photochromic Responses in Polymer Matrices

Ramachandran

Urban

2011

Handbook of Stimuli‐Responsive Materials

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IntroductionMany concepts of photochromic systems have been inspired by nature. An illustrative example is the reversible shape changes of the photoreceptor molecule rhodopsin in eyes that produces a cascade of molecular rearrangements responding to light illumination [1]. Upon photoexcitation, all-trans retinal undergoes isomerization to 11-cis across the double bond, thus causing shape changes. Although this event occurs at the angstrom (Å) level, there are many molecular interconnected events and responses that are not fully understood. Similar processes have been observed in certain molecules in materials chemistry, although on a much smaller and at a less-orchestrated scale. These are known as photochromic molecules, which were discovered over 150 years ago in an organic crystal of tetracene, and later on, in inorganic and organometallic materials [2][3][4]. In spite of a long research history, a quest for new photochromic materials continues. Color changes induced by ultraviolet (UV) radiation caused by trans − − cis isomerization, ring opening-closing reactions, inter-or intramolecular charge transfer, or bimolecular cycloaddition reactions are of particular interest. To make use of their photochromic behavior in various applications, photochromic entities are often incorporated into polymer matrices.While creating individual molecules and understanding their electronic properties facilitated further advances in understanding molecular mechanisms governing photochromism, useful applications require fabrication into films, sheets, fibers, or beads. This is typically achieved by incorporating photochromic molecules into macromolecular matrices by doping or dispersing, or covalently attaching them onto a polymer backbone. Since photoisomerization of chromophores alter equilibrium conformations, the dimensions of the surrounding polymer matrix play an essential role in spatial rearrangements. The dimensional classifications of the matrix effect have been extensively examined [5], with notable applications in ophthalmic lens, optical storage media, photosensors, and biomedical devices. Furthermore, the kinetics of conformational changes of polymers with photochromic moieties depends upon their physical or chemical incorporation into the matrix [6]. As one Handbook of Stimuli-Responsive Materials. Edited by Marek W. Urban

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“…In previous literatures, numerous photochromic properties of diarylethene derivatives have been carried out (Yumoto, K. et al 2008, Morimitsu, K. et al 2002. However, there are few publications reported photochromic unsymmetrical hybrid diarylethene derivatives with methoxyphenyl moieties.…”

Section: Introductionmentioning

confidence: 99%

Synthesizes and Properties of 1-[2-methyl-5-(4-fluorophenyl)-3- thienyl]-2-[2-methyl-5-(3-methoxy-4-formyphenyl)-3-thienyl] perfluorocyclopentene

Duan¹,

Liu²

2017

dtmse

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A novel unsymmetrical photochromic diarylethene 1-[2-methyl-5-(4-fluorophenyl)-3-thienyl]-2-[2-methyl-5-(3-methoxy-4-formyphenyl)-3-thienyl]perfluorocyclopentene(1o), was successfully synthesized and its properties were investigated in detail, including photochromic reactivity kinetics and concentration effect. The results showed that the compound exhibited remarkable photochromism, changing between colorless and blue in solution by photoirradiation, respectively. What is more, the kinetic experiments illustrated that the cyclization/cycloreversion process of this compound was determined to be the zeroth/first reaction.

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Dithienylethenes with a Novel Photochromic Performance

Cited by 152 publications

References 22 publications

Effects of substitution on the optoelectronic properties of photochromic diarylethenes bearing a pyrrole moiety

Effects of substitution on the optoelectronic properties of photochromic diarylethenes bearing a pyrrole moiety

Photochromic Responses in Polymer Matrices

Synthesizes and Properties of 1-[2-methyl-5-(4-fluorophenyl)-3- thienyl]-2-[2-methyl-5-(3-methoxy-4-formyphenyl)-3-thienyl] perfluorocyclopentene

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