Temperature dependence of the photoinduced micro-crystalline surface topography of a diarylethene

Fujinaga, Noriko; Nishikawa, Naoki; Sakiyama, Shingo; Yamazoe, Seiji; Kojima, Yoshitaka; Tsujioka, Tsuyoshi; Yokojima, Satoshi; Nakamura, Shinichiro; Uchida, Kôji

doi:10.1039/c3ce41336e

Cited by 8 publications

(16 citation statements)

References 24 publications

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“…13 The confinement of the crystal lattice is relaxed upon UV irradiation. Photogenerated crystals of the closed-ring isomers self-aggregates to form the microcrystals of the closed-ring isomers on the surface via the softened states.…”

Section: Resultsmentioning

confidence: 99%

“…The residue was purified with silicagel chromatography to obtain 0.79 g (1.48 mmol) of 4o as colorless prisms in 28% yields. (a-p)), 1.08 (d, 3H, J=6.8 Hz (a-p)), 1.28 (d, 3H, J=6.8 Hz (p)), 1.31 (d, 3H, J=6.8 Hz (p)),1.80 (s, 3H, Ar-CH 3 (a-p)), 2.01 (s, 3H, Ar-CH 3 (a-p)), 2.22 (s, 3H, Ar-CH 3 (p)), 2.49 (s, 3H, Ar-CH 3 (p)), 3.07 (sep, 1H, J=6.8 Hz (a-p)), 3.09 (sep, 1H, J=6.8 Hz (p)), 7.17-7.40 (m, 14H, ((p)+(a-p)), 7.63-7.67 (m, 2H, ((p)+(a-p))), 7.76 (d, 2H, J=7.8 Hz ((p)+(a-p))) ppm, 13 were collected by the ω scan with a width of 0.3°/frame on a Bruker SMART APEX CCD diffractometer with graphitemonochromatized Mo Kα radiation (λ= 0.71073 Å) at 93K. Data reduction was performed using SAINT software, which corrects for Lorentz and polarization effects, and decay.…”

Section: -(23-dimethyl-5-phenylthiophen-3-yl)-2-(2-isopropyl-1benzomentioning

confidence: 99%

“…11 The photo-induced reversible topographical changes by crystal growth of 1c and 1o via softened surface of the single crystals and microcrystalline film were observed above T g of 1o. 13 While step and valley formation on the crystalline surface was observed below T g of 1o. These appearances of the phenomena are characterized by the T g where the molecular confinement by crystalline lattice is drastically changed.…”

Section: Introductionmentioning

confidence: 96%

“…Upon UV irradiation, photogenerated 1c self-aggregates each other to form the microcrystals of 1c on the surface via the softened state. 13 We have previously reported the photogenerated crystal of cubic and needleshaped crystals upon UV irradiation. Plate-shaped crystals remained as unknown.…”

Section: Introductionmentioning

confidence: 99%

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Photoinduced topographical changes on microcrystalline surfaces of diarylethenes

et al. 2016

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DSC curves measured for a mixture of 4o and 4c, absorption spectral changes of 4o, thermal stability of 4c, force curves obtained by SPM on single crystalline surfaces and relation between temperatures and slope of force curves By alternate irradiation with UV and visible lights, reversible topographical changes were observed on the microcrystalline surfaces of diarylethene derivatives above the glass transition temperatures (T g ) of their open-ring isomers. For the photogenerated closed-ring isomers, the crystal growth proceeded at the surface softened by molecular movement. This is self-aggregation of the closed-ring isomers. The photogenerated surface topographies appear depending on their crystal habits of the closed-ring isomers. Reflecting the properties (crystal habits) of diarylethene derivatives, we obtained cubic, needle, and plate-shaped crystals of the closed-ring isomers on the microcrystalline surfaces of the open-ring isomers by the irradiation with UV light. Even a derivative having one isopropyl group at a reactive carbon atom, whose closed-ring isomer is thermally unstable, showed the photoinduced topographical changes, because the T g of open-ring isomer is around ambient temperatures. Scheme 1. Molecular structures of open-(o) and closed-ring (c) isomers of the diarylethenes 1, 2, 3, and 4.

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Section: Resultsmentioning

confidence: 99%

Section: -(23-dimethyl-5-phenylthiophen-3-yl)-2-(2-isopropyl-1benzomentioning

confidence: 99%

Section: Introductionmentioning

confidence: 96%

Section: Introductionmentioning

confidence: 99%

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Photoinduced topographical changes on microcrystalline surfaces of diarylethenes

et al. 2016

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“…The topographies of the microcrystalline surfaces of 2 o–4 o before and after UV irradiation are summarized in Figure in comparison to those of 1 o . Diarylethene 2 o has a rough surface covered with crystals . After UV irradiation followed with storage in the dark at 115 °C, which is lower than the eutectic temperature of 121 °C, the surface was covered by small lumps of 2 c crystals having a diameter of around 1 μm (Figure e).…”

Section: Photoinduced Topographical Changes On Diarylethene Microcrysmentioning

confidence: 99%

Photochromic Crystalline Systems Mimicking Bio‐Functions

Uchida

Nishimura

Hatano

et al. 2018

Chemistry A European J

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Photoresponsive crystalline systems mimicking bio-functions are prepared using photochromic diarylethenes. Upon UV irradiation of the diarylethene crystal, the photogenerated closed-ring isomers self-aggregate to form needle-shaped crystals on the surface. The rough surface shows the superhydrophobic lotus effect. In addition, the rose-petal effects of wetting, the anti-reflective moth-eye effect, and a double-roughness structure mimicking the surface of a lotus leaf are observed by controlling the heating procedures, UV irradiation processes, and molecular structural modification. By changing the molecular structure, a superhydrophilic surface mimicking a snail shell can be generated. We also find the crystal of a diarylethene derivative that shows a photosalient effect. The effect is observed partly due to the hollow structure of the crystal. It is demonstrated that a photo-response similar to the response of impatiens plant to stimulation is observed by packing small beads in the hollow. These photoresponsive functions are unique, and they demonstrate a macroscopic response by means of microscopic molecular movement induced by light. In the future, such a molecular assembly system will be a promising candidate for fabricating photoresponsive architectures and soft robots.

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Photoinduced Reversible Topographical Changes on Photochromic Microcrystalline Surfaces

Uchida

2015

Advances in Organic Crystal Chemistry

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Temperature dependence of the photoinduced micro-crystalline surface topography of a diarylethene

Cited by 8 publications

References 24 publications

Photoinduced topographical changes on microcrystalline surfaces of diarylethenes

Photoinduced topographical changes on microcrystalline surfaces of diarylethenes

Photochromic Crystalline Systems Mimicking Bio‐Functions

Photoinduced Reversible Topographical Changes on Photochromic Microcrystalline Surfaces

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