Mechanoresponsive turn-on phosphorescence by a desymmetrization approach

Tani, Yosuke; Komura, Mao; Ogawa, Takuji

doi:10.1039/d0cc01949f

Cited by 24 publications

(28 citation statements)

References 43 publications

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“…Diketone 3 was synthesised by the cross-benzoin condensation of the corresponding aldehydes, followed by oxidation (see ESI † for details). 9 After purification, overnight solvent removal at reduced pressure and 40 °C afforded 3 as a liquid ( Fig. 1c ); as-prepared 3 was confirmed to be pure and solvent-free by 1 H NMR and 13 C NMR spectroscopy, and elemental analysis.…”

Section: Resultsmentioning

confidence: 98%

“…S7 † ). 9 In addition, density functional theory (DFT) calculations at the UB3LYP-D3/6-311G(d) level of theory suggest that the most stable conformer of 3′ (in which the silyl groups in 3 are replaced by H) in the lowest triplet state (T 1 ) is the TP conformer ( Fig. 2c , S12, and Table S1 † ).…”

Section: Resultsmentioning

confidence: 99%

“…1b ). 9 Notably, unlike typical chromophores with rigid skeletons, the diketone skeleton is flexible, with five distinct conformers. Among them, a trans -planar (TP) conformer has two-fold intramolecular chalcogen bonds and is responsible for the efficient RTP in the amorphous solid states despite its minor proportion.…”

Section: Introductionmentioning

confidence: 99%

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Room-temperature phosphorescence of a supercooled liquid: kinetic stabilisation by desymmetrisation

2021

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Section: Resultsmentioning

confidence: 98%

Section: Resultsmentioning

confidence: 99%

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Room-temperature phosphorescence of a supercooled liquid: kinetic stabilisation by desymmetrisation

2021

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“…Furthermore, when bromine atoms were substituted by diverse linkage mode with different position or amount, improved phosphorescence performance can be achieved for BrFlu‐CBr (with Φ P =4.56 %), compared to other substituted modes (BrFlu‐C with 0.39 %, Flu‐CBr with 1.22 %, 2BrFlu‐CBr with 0.79 %) due to strong Br−Br interactions [44] . Thus, the linkage modes of substitutions not only adjust the molecular configurations and ICT effect through electronic effect and steric hindrance, but also influence intermolecular interactions in different directions, leading to the tunable RTP performance [45] …”

Section: Linkage Modes Of Substituentsmentioning

confidence: 98%

Substituent Effects in Organic Luminogens with Room Temperature Phosphorescence

Liao

2021

ChemPhotoChem

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Organic room temperature phosphorescence (RTP) materials have attracted much attention for their potential applications in various areas. Many diverse molecular design strategies have been proposed to achieve efficient intersystem crossing (ISC) and stable triplet excited states of organic materials. Among them, the introduction of substituents with different types, linkage positions and amounts, can play a key role in moderating the RTP effect resulting from their tunable electronic properties and steric hindrance. Minor differences between substituents can change the molecular packing in aggregated states significantly, facilitating improved RTP performance with rational design. This Concept reviews the relationship between substituent effects, aggregated structure and RTP properties by the systematic investigation of organic luminogens bearing different substituents. The aim of this Concept is to aid researchers so as to accelerate the development of RTP materials by providing insight into the internal mechanism and reviewing efficient strategies through the introduction of suitable substituents.

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“…[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. [206][207][208][209][210][211][212] Applications such as sensors, displays, memories, optical waveguides for hydrostatic or flex measurements, and light-emitting fabrics, [151,186,204,[213][214][215][216][217] represent a solid foundation for the spreading of mechanoresponsivity in the robotic communities. The self-healing properties found in several of the aforementioned systems are also of particular interest for soft robotics.…”

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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Mechanoresponsive turn-on phosphorescence by a desymmetrization approach

Abstract: Mechanoresponsive turn-on of room-temperature phosphorescence of a metal-free organic 1,2-diketone is reported. Desymmetrization selectively modifies the emission of the crystal.

Cited by 24 publications

References 43 publications

Room-temperature phosphorescence of a supercooled liquid: kinetic stabilisation by desymmetrisation

Room-temperature phosphorescence of a supercooled liquid: kinetic stabilisation by desymmetrisation

Substituent Effects in Organic Luminogens with Room Temperature Phosphorescence

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

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