Photosalient Phenomena that Mimic <i>Impatiens</i> Are Observed in Hollow Crystals of Diarylethene with a Perfluorocyclohexene Ring

Hatano, Eri; Morimoto, Masakazu; Imai, Takahito; Hyodo, Kengo; Fujimoto, Ayako; Nishimura, Rokuro; Sekine, Akiko; Yasuda, Nobuhiro; Yokojima, Satoshi; Nakamura, Shinichiro; Uchida, Kôji

doi:10.1002/anie.201706684

Cited by 87 publications

(61 citation statements)

References 32 publications

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“…[3] Such materials would combine the molecular order of single crystals with the properties of soft matter. [4] Av ariety of crystalline materials that display stimuliresponsive behaviour, [5] including breathable metal-organic frameworks, [6] spin-crossover materials, [7] thermosalience, [8] mechanosalience, [9] and photosalience [10] have been reported along with examples of both plastically [11] and elastically flexible crystals. [3a,8b, 12] Often, the fundamental mechanisms that lead to this behaviour are not well understood [11d,13] even though such materials may have applications in diverse areas from precision engineering to flexible electronics.…”

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Elastically Flexible Crystals have Disparate Mechanisms of Molecular Movement Induced by Strain and Heat

et al. 2018

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Elastically flexible crystals form an emerging class of materials that exhibit a range of notable properties. The mechanism of thermal expansion in flexible crystals of bis(acetylacetonato)copper(II) is compared with the mechanism of molecular motion induced by bending and it is demonstrated that the two mechanisms are distinct. Upon bending, individual molecules within the crystal structure reversibly rotate, while thermal expansion results predominantly in an increase in intermolecular separations with only minor changes to molecular orientation through rotation.

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confidence: 99%

Elastically Flexible Crystals have Disparate Mechanisms of Molecular Movement Induced by Strain and Heat

et al. 2018

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“…Locking the crystal through the introduction of supramolecular hydrogen‐bonding urethane motifs causes mechanical stress to build‐up upon UV light irradiation that results in the crystals “exploding” after accumulating enough stress . This rare phenomenon, termed the “photosalient effect,” could also be shown in the case of remarkable hollow‐shaped crystals of a DAE with the classical perfluorocyclohexene bridge, while single‐wall crystals of the same molecule experienced photoinduced bending . The intensity as well as the direction of incident light affect the resulting motion, for example, stepwise irradiation triggered delayed motion in certain DAE crystals, whereas irradiating a crystal with two different wavelengths of UV light triggered the crystal to move in two different directions.…”

Section: Crystalline Photoswitchable Materialsmentioning

confidence: 99%

Enlightening Materials with Photoswitches

2020

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reversible conversion between their stable and (meta)stable isomers triggered by light. The return to their native, thermo dynamically most stable isomer is gener ally induced by using another wavelength of light or simply by heat, depending on the thermal stability of the (meta)stable isomer. Retinal-the prototypical photo switch in biology-showcases impressively how structural changes occurring during a lightinduced doublebond isomerization can lead to vision or allow microorganisms to convert photons into metabolic energy. In analogy, over the years, scientists have learned that the lightdriven isomeriza tion of small molecules can be collected, possibly amplified, and transformed into macroscopic property changes, such as mechanical motion, [1] charge carrying ability, [2] assembly and disassembly of macroscopic aggregates, [3] as well as switching of surfaces and their properties. [4] Materials, which for the purpose of this review are consid ered to be solid objects or organized assemblies in solution, provide unique advantages to enhance the function of photo switches and even create new functions when compared to their standalone molecular selves (for the primarily discussed photochromic molecules herein, see Figure 1). One must, how ever, consider the inherent challenges that may present them selves when working with photoswitches in close proximity to one another. Intermolecular interactions, such as aggregation, excitation quenching, low freevolume, as well as the poten tially much higher optical density of materials can drastically lower the overall photoresponse. Yet with proper macromo lecular and supramolecular design, functions can be achieved through the incorporation of photoswitches in a material that simply cannot be obtained by an isolated molecule on its own. Here, we highlight recent examples from the literature that have appeared during the past decade since our previous review in this journal, [5] with particular focus on the order of the photos witches in relation to their environment and its impact on mate rial properties and device performance.Conceptually, one can think about maximizing a photo switching unit's effect by giving it "order" with relation to its surrounding, in particular to other switching units (Figure 2). The lowest possible order is undoubtedly demonstrated by dis persing photochromic molecules in a bulk amorphous material. If aggregation of the photoswitches can be overcome, switching units are placed in random orientation to each other giving rise to a more or less isotropic material. Starting from this scenario of randomly distributed photochromic entities, one can think about providing order in two dimensions by placing Incorporating molecular photoswitches into various materials provides unique opportunities for controlling their properties and functions with high spatiotemporal resolution using remote optical stimuli. The great and largely still untapped potential of these photoresponsive systems has not yet been fully exploited due to the fundamental challenge...

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“…Uchida and Morimoto et al. reported a hollow crystal of diarylethene (Figure a, b, and e) that displayed a remarkable photosalient phenomenon . Interestingly, it was observed that the flying debris released from the crystal exceeded several meters per second upon UV irradiation.…”

Section: Classification Of Photomechanical Organic Crystals Based On mentioning

confidence: 99%

Photomechanical Organic Crystals as Smart Materials for Advanced Applications

Aguila

Gao

et al. 2019

Chemistry A European J

102

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Photomechanical molecular crystals are receiving much attention due to their efficient conversion of light into mechanical work and advantages including faster response time; higher Young's modulus; and ordered structure, as measured by single‐crystal X‐ray diffraction. Recently, various photomechanical crystals with different motions (contraction, expansion, bending, fragmentation, hopping, curling, and twisting) are appearing at the forefront of smart materials research. The photomechanical motions of these single crystals during irradiation are triggered by solid‐state photochemical reactions and accompanied by phase transformation. This Minireview summarizes recent developments in growing research into photoresponsive molecular crystals. The basic mechanisms of different kinds of photomechanical materials are described in detail; recent advances in photomechanical crystals for promising applications as smart materials are also highlighted.

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Photosalient Phenomena that Mimic Impatiens Are Observed in Hollow Crystals of Diarylethene with a Perfluorocyclohexene Ring

Cited by 87 publications

References 32 publications

Elastically Flexible Crystals have Disparate Mechanisms of Molecular Movement Induced by Strain and Heat

Elastically Flexible Crystals have Disparate Mechanisms of Molecular Movement Induced by Strain and Heat

Enlightening Materials with Photoswitches

Photomechanical Organic Crystals as Smart Materials for Advanced Applications

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