Reversible Single-Crystal-to-Single-Crystal Phase Transition of Chiral Salicylidenephenylethylamine

Takanabe, Akifumi; Katsufuji, T.; Johmoto, Kohei; Uekusa, Hidehiro; Shiro, Motoo; Koshima, Hideko; Asahi, Toru

doi:10.3390/cryst7010007

Cited by 11 publications

(15 citation statements)

References 21 publications

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“…The DSC measurement revealed two sharp endothermic peaks at T c = 260.56 and 260.49 K on the first and second heatings, respectively, and a sharp exothermic peak at 255.89 K on cooling (Fig. 2), which indicated a reversible first-order transition similar to other reported phase transitions (Chen et al, 2015;Khan et al, 2015;Smets et al, 2015;Takanabe et al, 2017;Zeb et al, 2017). The observed enthalpy change and heat hysteresis are 4.34 J g À1 and 4.64 K. The average entropy change, ÁS, measured from the DSC curve is 0.0168 J g À1 K À1 or 6.4584 J mol À1 K À1 , and provided ÁS ¼ R ln N, then the possible configurations, N, equals to 2.17, indicating the two-site order-disorder characteristic of the studied transition (Asghar et al, 2016;Besara et al, 2011;Jain et al, 2009;Mą czka et al, 2014).…”

Section: Structural Phase Transition Of Hbasupporting

confidence: 81%

Temperature-induced order–disorder structural phase transitions of two-dimensional isostructural hexamethylenetetramine co-crystals

Chia

Quah

2017

Acta Crystallogr Sect B

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Hexamethylenetetramine-benzoic acid (1/2) (HBA) and hexamethylenetetramine-4-methylbenzoic acid (1/2) (HMBA) co-crystals undergo order-disorder structural phase transition from a low-temperature monoclinic crystal structure to a high-temperature orthorhombic crystal structure at the transition temperatures of 257.5 (5) K (Pn ↔ Fmm2) and 265.5 (5) K (P2/n ↔ Cmcm), respectively, using variable-temperature single-crystal X-ray diffraction analysis. The observed phase transitions were confirmed to be reversible first-order transitions as indicated by the sharp endothermic and exothermic peaks in the differential scanning calorimetry measurement. The three-molecule aggregate of HBA and HMBA consists of a hexamethylenetetramine molecule and two benzoic acid or two 4-methylbenzoic acid molecules, respectively. The acid molecules are ordered at the low-temperature phase and are equally disordered over two positions, which are related by a mirror symmetry, at the high-temperature phase. The two-dimensional supramolecular constructs common to both co-crystals are formed by three-molecule aggregates via weak intermolecular C-H...O and C-H...π interactions into molecular trilayers parallel to the ac plane with small XPac dissimilarity indices and parameters. The PIXEL interaction energies of all corresponding molecular contacts were calculated and the results are comparable between HBA and HMBA co-crystals, resulting in similar lattice energies and transition temperatures despite their two-dimensional isostructural relationship. The observed phase transitions of these two energetically similar co-crystals are triggered by similar mechanisms, i.e. the molecular rotator ordering and structural order-disorder transformation, which induced non-merohedral twinning with similar twin matrices in the low-temperature crystal form of both co-crystals.

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Section: Structural Phase Transition Of Hbasupporting

confidence: 81%

Temperature-induced order–disorder structural phase transitions of two-dimensional isostructural hexamethylenetetramine co-crystals

Chia

Quah

2017

Acta Crystallogr Sect B

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“…The difference in these transition enthalpies supports that enol-keto photoisomerization triggers the phase transition β → γ, but does not trigger the phase transition α → β due to a larger enthalpy. The enthalpy at the phase transition β → γ is also smaller than other structural phase transitions of molecular crystals 18,21,24,30,[33][34][35] .…”

Section: Discussionmentioning

confidence: 81%

Photo-triggered phase transition of a crystal

et al. 2019

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Structural phase transitions induced by external stimuli such as temperature, pressure, electromagnetic fields, and light play crucial roles in controlling the functions of solid-state materials. Here we report a new phase transition, referred to as the photo-triggered phase transition, of a photochromic chiral salicylideneamine crystal. The crystal, which exhibits a thermal single-crystal-to-single-crystal phase transition which is reversible upon heating and cooling, transforms to the identical phase upon light irradiation at temperatures lower than the thermal transition temperature. The photo-triggered phase transition originates from the strain of trans-keto molecules produced by enol-keto photoisomerization owing to the small energy barrier associated with changes in the crystal structure. The photo-triggered phase is metastable and returns to the initial stable phase via back isomerization from the trans-keto to enol form.

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“…The chiroptical and optical anisotropic properties of photomechanical Schiff bases were previously studied under UV irradiation [ 10 ]. Such properties as ferroelectricity, piezoelectricity and second-order optical non-linearity were reported [ 11 , 12 ].…”

Section: Introductionmentioning

confidence: 99%

Spectroscopic Identification of Hydrogen Bond Vibrations and Quasi-Isostructural Polymorphism in N-Salicylideneaniline

et al. 2021

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The ortho-hydroxy aryl Schiff base 2-[(E)-(phenylimino)methyl]phenol and its deutero-derivative have been studied by the inelastic incoherent neutron scattering (IINS), infrared (IR) and Raman experimental methods, as well as by Density Functional Theory (DFT) and Density-Functional Perturbation Theory (DFPT) simulations. The assignments of vibrational modes within the 3500–50 cm−1 spectral region made it possible to state that the strong hydrogen bond in the studied compound can be classified as the so-called quasi-aromatic bond. The isotopic substitution supplemented by the results of DFT calculations allowed us to identify vibrational bands associated with all five major hydrogen bond vibrations. Quasi-isostructural polymorphism of 2-[(E)-(phenylimino)methyl]phenol (SA) and 2-[(E)-(phenyl-D5-imino)methyl]phenol (SA-C6D5) has been studied by powder X-ray diffraction in the 20–320 K temperature range.

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Reversible Single-Crystal-to-Single-Crystal Phase Transition of Chiral Salicylidenephenylethylamine

Cited by 11 publications

References 21 publications

Temperature-induced order–disorder structural phase transitions of two-dimensional isostructural hexamethylenetetramine co-crystals

Temperature-induced order–disorder structural phase transitions of two-dimensional isostructural hexamethylenetetramine co-crystals

Photo-triggered phase transition of a crystal

Spectroscopic Identification of Hydrogen Bond Vibrations and Quasi-Isostructural Polymorphism in N-Salicylideneaniline

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