Thermosalient effect of two polymorphs of a diketopyrrolopyrrole dye with different crystal systems and molecular arrangements

So, Hee-Soo; Minami, Takaya; Jindo, Takumi; Matsumoto, Shinya

doi:10.1039/c8ce00940f

Cited by 28 publications

(26 citation statements)

References 36 publications

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“…corresponds to the melting point, whereas the first peak is relatively broad, corresponding to a polymorphic phase transition. This polymorphic phase transition indicates the thermosalient effect accompanied by mechanical behaviour, and the PXRD result of PR3Y right after the phase transition coincided with the results obtained for PR3O (So et al, 2018). This suggests that PR3O is thermodynamically more stable after the phase transition and the two polymorphs are in an enantiotropic relationship with each other.…”

Section: Figuresupporting

confidence: 82%

“…6 resulted in two different combinations of concomitant polymorphs. So et al (2018) and its chemical structure was confirmed by conventional analytical techniques. The crystallization of PR3C was carried out by liquid-liquid diffusion and the liquid-vapour diffusion method using a combination of various good (highly soluble) and poor (insoluble or less soluble) solvents ( Table 1).…”

Section: Tablementioning

confidence: 84%

“…In our earlier study on the occurrence of polymorphism of N,N 0 -bispropylated chlorinated-DPP dye [3,6-bis(4-chlorophenyl)-2,5-dipropyl-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione, hereafter abbreviated as PR3C], we found two polymorphs; furthermore, the yellow polymorph (PR3Y) was found to change into the orange polymorph (PR3O) with dynamical behaviour such as bursting, flipping and jumping upon heating. We determined that this dynamical behaviour might be associated with a sudden release of accumulated stress on one propyl group upon heating (So et al, 2018). We also obtained a new red polymorph (PR3R) in addition to PR3O and PR3Y ( Fig.…”

Section: Introductionmentioning

confidence: 83%

“…Crystallographic details.The crystal structures of PR3O and PR3Y have been published previously(So et al, 2018).…”

mentioning

confidence: 99%

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Three differently coloured polymorphs of 3,6-bis(4-chlorophenyl)-2,5-dipropyl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione

Matsumoto

2019

Acta Crystallogr Sect B

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In this paper, the conformational polymorphism of a chlorinated diketopyrrolopyrrole (DPP) dye having flexible substituents in a non-hydrogen-bonding system is reported. The propyl-substituted DPP derivative (PR3C) has three polymorphic forms, each showing a different colour (red, orange and yellow). All polymorphs could be obtained concomitantly under various crystallization conditions. The results of the crystal structure analysis indicate that PR3C adopts different conformations in each polymorph. The packing effect caused by the difference in the arrangement of neighbouring molecules was found to play an important role in the occurrence of the observed polymorphism. The thermodynamic stability relationship between the three polymorphs was identified by thermal analysis and indicates that the yellow polymorph is the thermally stable form. The results indicate that the yellow form and orange form are enantiotropically related, and the other polymorph is monotropically related to the others.

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Section: Figuresupporting

confidence: 82%

Section: Tablementioning

confidence: 84%

Section: Introductionmentioning

confidence: 83%

“…Crystallographic details.The crystal structures of PR3O and PR3Y have been published previously(So et al, 2018).…”

mentioning

confidence: 99%

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Three differently coloured polymorphs of 3,6-bis(4-chlorophenyl)-2,5-dipropyl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione

Matsumoto

2019

Acta Crystallogr Sect B

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“…The effect was first noted in 1983, and after a long hiatus, it was explored in greater detail in the anticholinergic agent oxitropium bromide in 2010 . Encouraged by these studies, over 20 new examples have been reported in the last decade that are categorized in three classes based on their structures, with a number of notable reports of serendipitous observations increasing in the past several years . It has also been demonstrated that the rates of the TS phase transitions are several orders of magnitude faster than other, more common solid–solid transitions .…”

Section: Introductionmentioning

confidence: 99%

Global Performance Indices for Dynamic Crystals as Organic Thermal Actuators

Karothu

Halabi

et al. 2020

Advanced Materials

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same basic thermodynamic principles of energy transduction and are collectively referred to as actuators. [1][2][3][4][5][6][7][8][9][10] While complex natural biomechanical systems have evolved to aid functions such as dispersal and survival, the artificially manufactured actuators are specifically designed for integration in mechatronic or adaptronic systems that range from miniature devices such as navigation and positioning systems in flying machines, to complex systems that can perform tasks in specific environments, such as humanoid robots and spacecraft. The current applications of actuators are many and diverse; they include sensors, [11,12] artificial muscles, [13] soft robotics, [14] and energy-harvesting materials. [15] Simple or complex actuating motions can be induced by heat, light, electricity, pressure, and moisture, among other stimuli, and can be realized with shape-memory polymers, [16] conductive fibers, [17] liquid crystal elastomers, [18] piezoelectric, [19] magnetostrictive, [20] and electromagnetic materials. [21] The energy supplied to the artificial actuators can vary from fluid pressure or flow in the pneumatics, to current, charge or voltage in the electromagnetic, piezoelectric and magnetostrictive actuators, to heat in shape memory and thermal expansion actuators.The active media in actuators include fluids, hard solids such as metals, and even complex soft matter such as tissuesensembles of cells with similar structure that act together to perform a specific function. While molecular crystals do not immediately appeal as working actuating medium, their dynamic properties have recently transpired as an alternative to other materials and they are thought to hold an untapped potential for miniature, soft actuating devices, quickly shaping up into a new research field, crystal adaptronics. [22,23] Smallscale demonstrations of the usefulness of molecular crystals as microscale devices, including cantilevers, [24,25] ratchets, [26] optical waveguides, [27][28][29][30][31][32][33][34][35][36] and other "crystal gears" [37] that can move or reshape are occasionally reported for dynamic crystals. Although being very illustrative, these demonstrations have thus far remained limited to a laboratory scale and have not been implemented in actual, functional devices. Some of the obstacles toward wider applications are difficulties with reproducible growth of crystals of predictable size without the use Crystal adaptronics is an emergent materials science discipline at the intersection of solid-state chemistry and mechanical engineering that explores the dynamic nature of mechanically reconfigurable, motile, and explosive crystals. Adaptive molecular crystals bring to materials science a qualitatively new set of properties that associate long-range structural order with softness and mechanical compliance. However, the full potential of this class of materials remains underexplored and they have not been considered as materials of choice in an engineer's toolbox. A set of general performance metric...

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Bending, Jumping, and Self‐Healing Crystals

Naumov

Чижик

Commins

et al. 2019

Mechanically Responsive Materials for Soft Robotics

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Thermosalient effect of two polymorphs of a diketopyrrolopyrrole dye with different crystal systems and molecular arrangements

Abstract: Two polymorphs of a diketopyrrolopyrrole dye, one yellow and the other orange, were obtained.

Cited by 28 publications

References 36 publications

Three differently coloured polymorphs of 3,6-bis(4-chlorophenyl)-2,5-dipropyl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione

Three differently coloured polymorphs of 3,6-bis(4-chlorophenyl)-2,5-dipropyl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione

Global Performance Indices for Dynamic Crystals as Organic Thermal Actuators

Bending, Jumping, and Self‐Healing Crystals

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