Stimulus-Responsive Supercooled π-Conjugated Liquid and Its Application in Rewritable Media

Sato, Yuika; Mutoh, Yuichiro; Morishita, Shuhei; Tsurumachi, Noriaki; Isoda, Kyosuke

doi:10.1021/acs.jpclett.1c00247

Cited by 8 publications

(4 citation statements)

References 47 publications

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“…RESPONSIVE MATERIALS triggers for crystallizing supercooled liquids because they can generate crystal nuclei. Similar to other examples, the phase transition of a supercooled liquid induced by mechanical force has been reported in N-heteroacene derivatives [141] and cyanostilbene derivatives. [142] Another attempt at a response to mechanical force is mechanically induced fluorescence color changes (MIFCs) derived from microscale phase separation.…”

Section: Mechanical Force Stimulisupporting

confidence: 81%

“…In addition to shearing, ultrasonic waves and adding sea sand are practical triggers for crystallizing supercooled liquids because they can generate crystal nuclei. Similar to other examples, the phase transition of a supercooled liquid induced by mechanical force has been reported in N ‐heteroacene derivatives [141] and cyanostilbene derivatives [142] …”

Section: Mechanical Force Stimulisupporting

confidence: 78%

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Responsive molecular liquid materials

Tateyama

Nakanishi

2023

Responsive Materials

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This review focuses on solvent‐free molecular liquid materials that exhibit changes in response to stimuli. Along with the recent development of soft functional materials, research on functional liquids possessing free deformability and ease of molding is becoming a new trend. A typical method for designing functional molecular liquids (FMLs) introduces flexible alkyl side‐chains around a π‐conjugation unit at the center of the molecule. As a result, the aggregation between π‐conjugated units is inhibited, and an entropy‐rich room temperature liquid is obtained. FMLs designed in this way can exhibit unique and exciting stimulus responses due to the high density of functional units and fluidity. Such notable features include electrochromism, phase transitions, and dynamic changes in the nanostructure. In addition, some stimulus responses are reversible and thanks to the fluidity, return to their initial state under relatively mild conditions, such as room temperature or slight heating. To elicit such effective stimulus responses, selecting an optimal π‐core, and modifying it with the appropriate alkyl side‐chains (length, branching, and substitution position) is essential. A deep understanding of the alkyl–π molecular design will enable the creation of more attractive stimuli‐responsive FMLs, which are of high value in advanced fields such as healthcare, security, sensors, soft electronics, and robotics.

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Section: Mechanical Force Stimulisupporting

confidence: 81%

Section: Mechanical Force Stimulisupporting

confidence: 78%

Responsive molecular liquid materials

Tateyama

Nakanishi

2023

Responsive Materials

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“…Although supercooling can complicate the search for thermodynamically stable functional molecular liquids and on-demand energy release from heat storage media, , it also presents opportunities to create new types of stimuli-responsive functional materials. Examples include mechanically induced crystallization of an SCL that can be used for rewritable inks, − as well as phase change materials that store heat that can be released when solidification is induced . The ability of SCLs to undergo solidification when exposed to a specific stimulus is key to their utility.…”

Section: Introductionmentioning

confidence: 99%

Robust Supercooled Liquid Formation Enables All-Optical Switching Between Liquid and Solid Phases of TEMPO

Rodriguez,

Lam,

Anwar

et al. 2024

ACS Omega

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Organic molecules that undergo supercooling can provide the basis for novel stimuli-responsive materials, but the number of such compounds is limited. Results in this paper show that the stable organic radical 2,2,6,6-tetramethyl-1-piperidine-1-oxyl (TEMPO) can form a stable supercooled liquid (SCL). Upon melting and cooling back to room temperature, the TEMPO SCL can persist for months, even after mild physical agitation. Its high vapor pressure can enable crystal growth at remote locations within the sample container over the course of days. Optical, electron paramagnetic resonance, and birefringence measurements show no evidence of new chemical species or partially ordered phases in the supercooled liquid. TEMPO's free radical character permits absorption of visible light that can drive photothermal melting to form the SCL, while a single nanosecond light pulse can initiate recrystallization of the SCL at some later time. This capability enables all-optical switching between the solid and the SCL phases. The physical origin of TEMPO's remarkable stability as an SCL remains an open question, but these results suggest that organic radicals comprise a new class of molecules that can form SCLs with potentially useful properties.

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“…[34][35][36][37] There are only limited examples of liquid materials exhibiting phasedependent changes in luminescence, and for most of these materials, the luminescence is more intense in the crystal form than that in the liquid form. [38][39][40][41] Such materials would exhibit emission fading during melting, and this would hinder the visualization of the local disordering process.…”

mentioning

confidence: 99%

Light-melting Diketone Crystal with ON-OFF-ON Luminescence Evolution

Komura

Sotome

Miyasaka

et al. 2022

Preprint

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Crystal melting by light irradiation, that is, the phenomenon of photoinduced crystal-melt transition (PCMT), can dramatically change material properties with high spatiotemporal resolution. However, both the process and mechanism of PCMT remain unknown owing to a lack of suitable probes and the poor diversity of compounds exhibiting PCMT. Here, we report the first instance of PCMT with luminescence evolution. We show that a heteroaromatic 1,2-diketone crystal exhibits ON-OFF-ON luminescence changes under continuous ultraviolet irradiation, which can be ascribed to the sequential PCMT processes of crystal loosening and conformational isomerization before macroscopic melting. Single-crystal X-ray structural analysis, thermal analysis, and theoretical calculations of three diketones revealed that weak intermolecular interactions and the presence of a disordered layer in the crystal are essential for PCMT. Our results provide fundamental insights into the melting process of molecular crystals and should aid the molecular design of PCMT-active materials that are based on emissive compounds, as opposed to the classical molecular designing based on nonemissive photochromic scaffolds such as azobenzenes.

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Stimulus-Responsive Supercooled π-Conjugated Liquid and Its Application in Rewritable Media

Cited by 8 publications

References 47 publications

Responsive molecular liquid materials

Responsive molecular liquid materials

Robust Supercooled Liquid Formation Enables All-Optical Switching Between Liquid and Solid Phases of TEMPO

Light-melting Diketone Crystal with ON-OFF-ON Luminescence Evolution

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