Two novel rhodamine-based molecules with different mechanochromic and photochromic properties in solid state

Ma, Zhiyong; Ji, Ya-Jian; Lan, Youshi; Kuang, Gui‐Chao; Jia, Xinru

doi:10.1039/c8tc00145f

Cited by 34 publications

(26 citation statements)

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“…Therefore, it is of great significance to fabricate sensor materials with multiple functions to further widen the scope of application in different fields. [32][33][34][35][36][37] However, reports on such materials are very rare.…”

Section: Introductionmentioning

confidence: 99%

An ESIPT-based fluorescent switch with AIEE, solvatochromism, mechanochromism and photochromism

Liu

et al. 2019

Mater. Chem. Front.

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Section: Introductionmentioning

confidence: 99%

An ESIPT-based fluorescent switch with AIEE, solvatochromism, mechanochromism and photochromism

Liu

et al. 2019

Mater. Chem. Front.

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“…The pristine powder of 2a16 showed intense and sharp peaks, suggesting the crystalline state (Figure C). In contrast, the PXRD curve obtained by grinding showed lesser peaks, indicating that the powder had changed from the crystalline state to an amorphous one under the mechanical stress. − After fuming the ground powder in acetone, some new peaks were detected. The minor differences in their PXRD curves of the fumed powder and the pristine powder indicated that the powder had changed from one crystalline phase to another, which was also consistent with their different emission spectra between the pristine powder and the fumed powder (Figure B).…”

Section: Resultsmentioning

confidence: 97%

“…In contrast, the PXRD curve obtained by grinding did not exhibit obvious peak, indicating that the pristine powder had changed from the crystalline state to an amorphous one after mechanical stress. [43][44][45][46] Upon fuming the ground powder in acetone, some new peaks appeared. The partly different PXRD curves of fumed powder compared to those of the pristine powder demonstrated the change from one crystalline phase to another, which was also consistent with their different emission spectral between pristine powder and fumed powder (Figure 6B).…”

Section: Aie Properties Of 2a16mentioning

confidence: 99%

Development of Rofecoxib-Based Fluorescent Probes and Investigations on Their Solvatochromism, AIE Activity, Mechanochromism, and COX-2-Targeted Bioimaging

Xie

Zheng

et al. 2021

Anal. Chem.

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Cyclooxygenase-2 (COX-2) fluorescent probes are promising tools for early cancer diagnosis. Traditionally, COX-2 probes were designed by connecting two parts, a fluorophore and a COX-2 binding unit, via a flexible linker. Herein, a new class of COX-2-specific fluorescent probes have been developed by one-step modification from rofecoxib by an integrative approach to combining the fluorophore and binding units into one. Among them, several new rofecoxib analogues not only retained their COX-2 binding ability but also exhibited attractive fluorescent properties, such as tunable Blue-Red emission, solvatochromism, AIE behavior and mechanochromism. Notably, the emission of 2a16 can be switched between greenish-yellow in the crystalline state to red-orange in the amorphous state by grinding and fuming treatments. Furthermore, the highly fluorescent compound 2a16 (Фf = 0.94 in powder) displayed much stronger fluorescent imaging of COX-2 in HeLa cancer cells overexpressing COX-2 than RAW264.7 normal cells with minimal expressing of COX-2. Most importantly, 2a16 can light up human cancer tissues from adjacent normal tissues with much brighter fluorescence by targeting COX-2 enzyme. These results illustrate the potential of 2a16 as a new red fluorescent probe for human cancer imaging in clinical applications.

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“…[159,162,186,187] Interestingly, many of these systems could act sinergically with covalently-bound ones, yielding to more precise information about the mechanical history of the devices. [188] We summarized examples of the most common mechanoresponsive units found in the scientific literature in Figure 5, organizing them between those moieties that are covalently linked to polymers (Figure 5a) [169,170,[195][196][197][198][199][200][201]178,179,[189][190][191][192][193][194] and those molecules that are employed as dispersions in polymeric matrices (Figure 5b). [159,162,176,[202][203][204] The list is not exhaustive and for mechanochromic materials we address the reader to the comprehensive reviews of Sagara et al [150] and Chen et al [205] Moreover, several innovative molecular systems which can display different colors upon change of conformation or crystal structures, could expand the scope of mechanochromic materials in the near future, making more colorations available and improving the performances of the materials in terms of sensibility and reliability.…”

Section: From Cromatophore As Absorbance Elements Through Molecular Mechanochromic Devicesmentioning

confidence: 99%

A Perspective on Cephalopods Mimicry and Bioinspired Technologies toward Proprioceptive Autonomous Soft Robots

Giordano

Carlotti

Mazzolai

2021

Adv Materials Technologies

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scientific community. [1][2][3][4][5][6][7] Regardless, every time a living being reveals novel adaptive and dynamically reactive mimicry behavior, it inspires and fosters futuristic and unexpected technological outcomes. [8][9][10][11][12] At the biological level, the visual crypsis is the ability of a species to resemble the surroundings by matching the coloration and the geometrical patterns of the habitat. In this sense, a living being can control its appearance optically (thanks to arranged and optimized structures at the mesoscopic scale, by means of pigmentation, or emissive elements) and morphologically (it can show wrinkles and textures on the body to evade detection or observation). [13][14][15][16][17][18] Both these mechanisms are characterized by a time response that ranges from milliseconds to hundreds of seconds. In nature, several species take advantage of cryptic abilities, as, e.g., in cephalopods, [7] crustaceans, [19] reptilians, [1,20,21] insects, [22,23] birds, [24,25] shells, [26,27] plants, [28,29] among many. The biotic color changing and body patterning relate to reproductive, communicative, and defensive and/or predatory strategies. Unfortunately, the nervous or central control-chain system that steers these behaviors in animals and plants, is still somehow fogged for scientists. [7,[30][31][32] A complete knowledge about their central information process systems, can open to astonishing developments in many scientific branches, from neurobiology [33,34] to quantum biology. [35] Undoubtedly, the most debated case of study in the natural world are cephalopods, which not only are highly evolved and specialized in fast adaptive color changing displays, but also are able to actuate their skin to generate 3D patterns, when exposed to specific mechanical, thermal, optical, or chemical stimuli. Soft muscular arrangements, [36][37][38] spatially distributed and expandable absorbing components (namely chromatophores), [39,40] iridescent elements (namely irido phores), [41,42] and bright white scatterers (namely leucophores) [43] are responsible for textural, postural and color changing. Moreover, octopuses are a remarkable intelligent species, able, for example, to open a jar or avoid predators in the order of seconds. [44] Thus, cephalopods are usually regarded as a perfect example of embodied intelligence, [45] thanks to the symbiosis between their body's mechanics and morphology, and the distributed sensory neuro-motor-control system. Their "learning", "mechanical" and "material intelligence" will be our lodestars along this review, resulting in a fascinating connection between Octopus skin is an amazing source of inspiration for bioinspired sensors, actuators and control solutions in soft robotics. Soft organic materials, biomacromolecules and protein ingredients in octopus skin combined with a distributed intelligence, result in adaptive displays that can control emerging optical behavior, and 3D surface textures with rough geometries, with a remarkably high control speed (≈ms). To be able ...

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Two novel rhodamine-based molecules with different mechanochromic and photochromic properties in solid state

Abstract: Two novel molecules (AnRhB-1 and AnRhB-2) were synthesized using Rhodamine B and anthracene as building units via Schiff base chemistry with different spacers.

Cited by 34 publications

References 50 publications

An ESIPT-based fluorescent switch with AIEE, solvatochromism, mechanochromism and photochromism

An ESIPT-based fluorescent switch with AIEE, solvatochromism, mechanochromism and photochromism

Development of Rofecoxib-Based Fluorescent Probes and Investigations on Their Solvatochromism, AIE Activity, Mechanochromism, and COX-2-Targeted Bioimaging

A Perspective on Cephalopods Mimicry and Bioinspired Technologies toward Proprioceptive Autonomous Soft Robots

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