Ultimate diastereoselectivity in the ring closure of photochromic diarylethene possessing facial chirality

Shiozawa, Tatsuya; Hossain, Mohammed Kamrul; Ubukata, Takashi; Yokoyama, Yasushi

doi:10.1039/c0cc00240b

Cited by 38 publications

(9 citation statements)

References 48 publications

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“…1 : 1 in most cases unless the diarylethene derivative is characteristically designed to form the AP form. 31,32 In addition, the diarylethene derivative can thermally transform to each conformation in solution at room temperature. This is the reason why the cyclization conversion in solution upon irradiation with UV light is relatively high (69-97%) while the photocyclization quantum yield is around 50%.…”

Section: Photochromism Of Diarylethene Homopolymers In the Solid Statementioning

confidence: 99%

Photochromic polymers bearing various diarylethene chromophores as the pendant: synthesis, optical properties, and multicolor photochromism

2011

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Photochromic polymers with various diarylethene derivatives were synthesized by a conventional radical polymerization of styrene derivatives having diarylethene chromophores as the pendant. All the polymers exhibited reversible photochromism in the film as well as in solution, while the photocyclization conversion in the film decreased in comparison with that in solution because of a restriction of the conformational structure in the solid state. Although the photocyclization and photocycloreversion quantum yields at the initial stage of the reactions in the film were comparable to those in solution, the apparent cycloreversion quantum yield decreased along with the reaction, which is derived from a distribution of the quantum yields in the solid state. Finally, the photochromic terpolymers consisting of three diarylethene monomers which show photochromism changing color to cyan, magenta, and yellow were synthesized. The terpolymers were demonstrated to show bright colors including black, green, red, and blue both in solution and in the solid state by selective bleaching processes. Such multicolor photochromic polymers composed of diarylethene derivatives have a potential for rewritable photochromic display devices.

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Section: Photochromism Of Diarylethene Homopolymers In the Solid Statementioning

confidence: 99%

Photochromic polymers bearing various diarylethene chromophores as the pendant: synthesis, optical properties, and multicolor photochromism

2011

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“…Diarylethene derivatives , are one of the representative systems whose photochromic properties originate from photoinduced cyclization (ring-closing) and cycloreversion (ring-opening) reactions with high thermal stability and durability to the photodegradation. A number of investigations on the switching of physical and chemical properties through cyclization and cycloreversion reactions have been conducted, − and specific excitation methods have opened new functionality such as multiphoton-gated photochromism, − one-color reversible reactions, and plasmon-coupled photoreactions . Moreover, it was found for several derivatives that the morphology change of the crystals can be induced through the photochromic reaction in the crystalline phase, , and this property is expected to apply into the mesoscopic photodriven actuators. − …”

Section: Introductionmentioning

confidence: 99%

Solvent Polarity Dependence of Photochromic Reactions of a Diarylethene Derivative As Revealed by Steady-State and Transient Spectroscopies

et al. 2016

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Solvent polarity dependence of photochromic reactions such as cyclization and cycloreversion of a photochromic diarylethene derivative, 1,2-bis(2-methyl-3-benzothienyl)perfluorocyclopentene, was investigated by steady-state spectroscopic and femtosecond laser photolysis methods. For the cyclization reaction, it was revealed that the quantum yield decreased with an increase in solvent polarities, mainly due to the decrease in the fraction of the conformer with C 2 symmetry favorable for the cyclization. This result indicated that the branching ratio for the cyclization and the deactivation to the open-ring isomer at the conical intersection was almost independent of the solvent polarity. On the other hand, it was found for the cycloreversion process that the closed-ring isomer in the S1 state rapidly deactivated into the ground state in competition with the activated process leading to the conical intersection providing a pathway toward both open- and closed-ring minima in the ground state. The cycloreversion reaction quantum yield also decreasing with an increase in the solvent polarity was attributed to larger increase of the direct deactivation into the ground state from the excited state minimum of the closed-ring isomer.

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“…We have focused our efforts on achieving high diastereoselectivity in the photochromism of diarylethenes with the aid of chiral factors such as asymmetric stereogenic carbon atoms or an axially or facially chiral unit, introduced within the molecules themselves 2. So far, we have achieved completely diastereoselective ring‐closing reactions with several compounds 2a,b,d. However, although the highly enantioselective photochromic reactions of diarylethenes in a chiral crystalline state have been reported,3 those in solution have yet to be achieved 4…”

Section: Methodsmentioning

confidence: 99%

Enantioselective Photochromism of Diarylethenes in Human Serum Albumin

Fukagawa

Kawamura

Ubukata

et al. 2013

Chemistry A European J

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Ultimate diastereoselectivity in the ring closure of photochromic diarylethene possessing facial chirality

Abstract: A bisthienylethene with hitherto unprecedented facial chirality imposed by a triethyleneglycol bridge on a thiophene ring was synthesized and its photochromic ring closure was shown to occur with 100% diastereoselectivity upon UV-light irradiation.

Cited by 38 publications

References 48 publications

Photochromic polymers bearing various diarylethene chromophores as the pendant: synthesis, optical properties, and multicolor photochromism

Photochromic polymers bearing various diarylethene chromophores as the pendant: synthesis, optical properties, and multicolor photochromism

Solvent Polarity Dependence of Photochromic Reactions of a Diarylethene Derivative As Revealed by Steady-State and Transient Spectroscopies

Enantioselective Photochromism of Diarylethenes in Human Serum Albumin

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