Recent progress in the design of conjugated polydiacetylenes with reversible thermochromic performance: a review

MuYu, Congcong; Zhao, Jingying; Yang, Guang

doi:10.1039/d3py00213f

Cited by 13 publications

(4 citation statements)

References 97 publications

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“…Indeed, although the 52.8°angle is slightly off from the optimal 45°angle, the 3.91 Å distance between the reactive carbons C11/C11′ is slightly shorter than 4 Å, and the stacking translation distance (d = 4.79 Å) of the monomers (Figure 3) is close to the optimal value of 4.9 Å. The calculated density of the single crystal of DA4 is 1.258 g/cm 3 , which turns out to be similar to that of the calculated density of the DA2 isomer (1.252 g/cm 3 ). However, unlike DA2, DA4 crystal reacts to light at room temperature swiftly (minute timescale), becoming increasingly pink over time, thus witnessing the polymerization event.…”

Section: Da4 (Rs-meso-isomermentioning

confidence: 84%

“…The supramolecular assembly and crystal engineering of functional polydiacetylenes (PDAs) generate smart materials, which respond to stimuli such as pH, temperature, and chemical and biological targets . The PDAs are not only pH- and thermochromic but also photo-, mechano-, and radiochromic, , dominated by a transition between a nonemissive form, sometimes called the “blue” form, and a fluorescent state (“red” form) .…”

Section: Introductionmentioning

confidence: 99%

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Selective Chirality-Driven Photopolymerization of Diacetylene Crystals

Baillargeon,

Boivin,

Vaillancourt

et al. 2024

Crystal Growth & Design

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Crystal engineering of two diacetylene monomers was achieved by branching two chiral groups [R = PhC*MeNH(CO2)CH2] exhibiting an enantiopure configuration of S,S-(DA2) and an achiral R,S-meso-isomer (DA4). The X-ray structures of DA2 and DA4 reveal the presence of supramolecular arrangements driven by intermolecular H-bonding. A significant intermolecular closer proximity in DA4 than that in DA2 is depicted, ultimately resulting in a slow thermal (days) and swift (min) photochemical polymerization of DA4 to form PDA5, whereas DA2 is unreactive. DFT computations indicate that in both cases the lowest energy-excited state is the charge-transfer state [CT; PhC*MeNH(CO2) → π*(−CC–CC−)]. Therefore, this outcome illustrates a drastic selectivity via a settle change in a carbon configuration. Analysis demonstrates that PDA5 is nonemissive and that its coloration arises from a π → π* excitation of the polymer backbone (DFT computations).

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Section: Da4 (Rs-meso-isomermentioning

confidence: 84%

Section: Introductionmentioning

confidence: 99%

Selective Chirality-Driven Photopolymerization of Diacetylene Crystals

Baillargeon,

Boivin,

Vaillancourt

et al. 2024

Crystal Growth & Design

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“…[ 56–62 ] The stimuli responsivity has been tuned by the control of the flexibility in the organized states, such as molecular design of diacetylene (DA) monomers and intercalation of the guests in the interlayer space of the self‐assembled amphiphilic DA molecules. [ 63–73 ] However, mechanical stresses other than shear stress are not detected only using PDA because the molecular motion is not induced by the mechanical stresses. In our previous works, responsiveness to compression and weak frictional stress was achieved by combining mechanoresponsive capsule integrated in the device.…”

Section: Introductionmentioning

confidence: 99%

High‐Sensitive Spatiotemporal Distribution Imaging of Compression Stresses Based on Time‐Evolutional Responsiveness

Ono,

Seishima,

Shigeta

et al. 2024

Small

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Mechanoresponsive materials have been studied to visualize and measure stresses in various fields. However, the high‐sensitive and spatiotemporal imaging remain a challenging issue. In particular, the time evolutional responsiveness is not easily integrated in mechanoresponsive materials. In the present study, high‐sensitive spatiotemporal imaging of weak compression stresses is achieved by time‐evolutional controlled diffusion processes using conjugated polymer, capsule, and sponge. Stimuli‐responsive polydiacetylene (PDA) is coated inside a sponge. A mechanoresponsive capsule is set on the top face of the sponge. When compression stresses in the range of 6.67–533 kPa are applied to the device, the blue color of PDA is changed to red by the diffusion of the interior liquid containing a guest polymer flowed out of the disrupted capsule. The applied strength (F/N), time (t/s), and impulse (F·t/N s) are visualized and quantified by the red‐color intensity. When a guest metal ion is intercalated in the layered structure of PDA to tune the responsivity, the device visualizes the elapsed time (τ/min) after unloading the stresses. PDA, capsule, and sponge play the important roles to achieve the time evolutional responsiveness for the high‐sensitive spatiotemporal distribution imaging through the controlled diffusion processes.

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“…in polar organic solvents. Although covalent modification of DA monomer or PDA can theoretically improve the stability of blue phase PDAs in polar organic solvents, 30,31 alteration in DA or PDA structure may cause more indeterminacy in topological polymerization ability of monomer or sensitivity to external stimuli of the polymers 32–34 . Therefore, preparing the blue phase PDA‐based sensors with stimuli‐responsive colorimetric in polar organic solvents by a simple method without intrinsically changing the structure is in need to expanding their sensing application.…”

Section: Introductionmentioning

confidence: 99%

Stimuli‐responsive colorimetric polydiacetylene sensor in polar organic solvent

Ma,

Hu,

Jiang

et al. 2023

J of Applied Polymer Sci

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Polydiacetylene (PDA) has been actively employed as sensing vehicles owing to its unique colorimetric feature upon environmental stimulation. Here, blue phase PDA has been constructed by topological polymerization of commercial diacetylene acid (DA) noncovalently modified by guest amines. Specifically, PDA including 1‐naphthylmethylamine noncovalently bonded on both sides exhibits long‐term stability in polar organic solvents. The stability of PDA depended upon both the structures of the DA and the guest molecule, underscoring a stabilizing mechanism dominated by noncovalent bonding and strong π–π interaction. Accordingly, the blue phase PDA shows a colorimetric response from blue to red upon exposure to stimuli influencing noncovalent bonding and π–π interaction, such as elevated temperature, the existence of acid or alkali at concentrations as low as 50 ppm. Therefore, the PDA developed in this study has the potential of serving as a colorimetric sensor for detecting subtle environment changes and especially for measuring the quality of polar organic solvents recovered from industrial effluent.

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Recent progress in the design of conjugated polydiacetylenes with reversible thermochromic performance: a review

Abstract: Π-conjugated polydiacetylenes (PDAs) have attracted enormous attention based on their unique structures and properties.

Cited by 13 publications

References 97 publications

Selective Chirality-Driven Photopolymerization of Diacetylene Crystals

Selective Chirality-Driven Photopolymerization of Diacetylene Crystals

High‐Sensitive Spatiotemporal Distribution Imaging of Compression Stresses Based on Time‐Evolutional Responsiveness

Stimuli‐responsive colorimetric polydiacetylene sensor in polar organic solvent

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